CATALYST FOR HYDROSILYLATION REACTION, HYDROGENATION REACTION, AND HYDROSILANE REDUCTION REACTION

Abstract

Provided is a catalyst which comprises a compound represented by formula (1) and which exhibits activity for at least one type of reaction selected from among hydrosilylation reaction or hydrogenation reaction with respect to an aliphatic unsaturated bond and hydrosilane reduction reaction with respect to a carbon-oxygen unsaturated bond or a carbon-nitrogen unsaturated bond. Formula (1): M.sub.n(L.sub.m) {M represents Fe, Co, or Ni having an oxidation number of 0, L represents an isocyanide ligand represented by formula (2), n denotes an integer of 1-8, and m denotes an integer of 2-12. Formula (2): (CN).sub.x—R.sup.1 (R.sup.1 represents a mono- to trivalent-organic group having 1-30 carbon atoms, optionally being substituted by a halogen atom, and optionally having interposed therein one or more atoms selected from among O, N, S, and Si; and x denotes an integer of 1-3)}.

Claims

1. A method for producing a product of a hydrosilylation reaction between an aliphatic unsaturated bond-containing compound and a Si—H bond-containing compound, wherein the method comprises contacting the aliphatic unsaturated bond-containing compound and the Si—H bond-containing compound with a catalyst comprising a compound represented by formula (1) below:
M.sub.n(L).sub.m  (1) wherein M represents Fe, Co, or Ni with an oxidation number of 0, L represents an isocyanide ligand represented by formula (2) below, n represents an integer of 1 to 8, and m represents an integer of 2 to 12,
(CN).sub.x—R.sup.1  (2) wherein R.sup.1 represents a monovalent to trivalent organic group that has 1 to 30 carbon atoms, and x represents an integer of 1 to 3, wherein the monovalent organic group that has 1 to 30 carbon atoms is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosanyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, norbornyl, adamantyl, phenyl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, o-biphenylyl, m-biphenylyl, p-biphenylyl, tolyl, 2,6-diisopropylphenyl, a mesityl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, and an arylalkyl group having 7 to 20 carbon atoms.

2. The method according to claim 1, wherein the aliphatic unsaturated bond-containing compound is an olefin compound, a silane compound or an organopolysiloxane having an alkenyl group bonded to a Si atom.

3. The method according to claim 1, wherein, in the formula (2), x is 1.

4. The method according to claim 1, wherein, in the formula (1), when n=1, m=2, 4, or 5, when n=2 to 4, m=an integer of 6 to 10, and when n=8, m=12.

5. The method according to claim 1, wherein, in the formula (1), when M is Fe, n=1 and m=5, when M is Co, n=2 and m=8, and when M is Ni, n=1 and m=2 or 4, or n=3, 4, or 8 and m=4, 6, 7, or 12.

6. The method according to claim 1, wherein M in the formula (1) is Fe or Co.

7. A method for producing a product of a hydrogenation reaction between an aliphatic unsaturated bond-containing compound and a Si—H bond-containing compound, wherein the method comprises contacting the aliphatic unsaturated bond-containing compound and the Si—H bond-containing compound with a catalyst comprising a compound represented by formula (1) below:
M.sub.n(L).sub.m  (1) wherein M represents Fe, Co, or Ni with an oxidation number of 0, L represents an isocyanide ligand represented by formula (2) below, n represents an integer of 1 to 8, and m represents an integer of 2 to 12,
(CN).sub.x—R.sup.1  (2) wherein R.sup.1 represents a monovalent to trivalent organic group that has 1 to 30 carbon atoms, and x represents an integer of 1 to 3, wherein the monovalent organic group that has 1 to 30 carbon atoms is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosanyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, norbornyl, adamantyl, phenyl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, o-biphenylyl, m-biphenylyl, p-biphenylyl, tolyl, 2,6-diisopropylphenyl, a mesityl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, and an arylalkyl group having 7 to 20 carbon atoms.

8. The method according to claim 2, wherein the aliphatic unsaturated bond-containing compound is an olefin compound, a silane compound or an organopolysiloxane having an alkenyl group bonded to a Si atom.

9. The method according to claim 2, wherein, in the formula (2), x is 1.

10. The method according to claim 2, wherein, in the formula (1), when n=1, m=2, 4, or 5, when n=2 to 4, m=an integer of 6 to 10, and when n=8, m=12.

11. The method according to claim 2, wherein, in the formula (1), when M is Fe, n=1 and m=5, when M is Co, n=2 and m=8, and when M is Ni, n=1 and m=2 or 4, or n=3, 4, or 8 and m=4, 6, 7, or 12.

12. The method according to claim 2, wherein M in the formula (1) is Fe or Co.

13. A method for producing a product of a reduction reaction between (i) a Si—H bond-containing compound and (ii) a compound having a carbon-oxygen unsaturated bond or a carbon-nitrogen unsaturated bond, wherein the method comprises contacting (i) the Si—H bond-containing compound and (ii) the compound having a carbon-oxygen unsaturated bond or the compound having the carbon-nitrogen unsaturated bond, with a catalyst comprising a compound represented by formula (1) below:
M.sub.n(L).sub.m  (1) wherein M represents Fe, Co, or Ni with an oxidation number of 0, L represents an isocyanide ligand represented by formula (2) below, n represents an integer of 1 to 8, and m represents an integer of 2 to 12,
(CN).sub.x—R.sup.1  (2) wherein R.sup.1 represents a monovalent to trivalent organic group that has 1 to 30 carbon atoms, and x represents an integer of 1 to 3, wherein the monovalent organic group that has 1 to 30 carbon atoms is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosanyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, norbornyl, adamantyl, phenyl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, o-biphenylyl, m-biphenylyl, p-biphenylyl, tolyl, 2,6-diisopropylphenyl, a mesityl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, and an arylalkyl group having 7 to 20 carbon atoms.

14. The method according to claim 13, wherein the compound having a carbon-oxygen unsaturated bond or a carbon-nitrogen unsaturated bond is an aldehyde compound, a ketone compound, an amide compound, or a nitrile compound.

15. The method according to claim 13, wherein, in the formula (2), x is 1.

16. The method according to claim 13, wherein, in the formula (1), when n=1, m=2, 4, or 5, when n=2 to 4, m=an integer of 6 to 10, and when n=8, m=12.

17. The method according to claim 13, wherein, in the formula (1), when M is Fe, n=1 and m=5, when M is Co, n=2 and m=8, and when M is Ni, n=1 and m=2 or 4, or n=3, 4, or 8 and m=4, 6, 7, or 12.

18. The method according to claim 13, wherein M in the formula (1) is Fe or Co.

Description

DESCRIPTION OF EMBODIMENTS

[0060] Below the invention is described in more detail.

[0061] The invention provides a catalyst including a compound represented by formula (1) below, and having activity in at least one reaction selected from hydrosilylation reaction or hydrogenation reaction on an aliphatic unsaturated bond and hydrosilane reduction reaction on a carbon-oxygen unsaturated bond or a carbon-nitrogen unsaturated bond.

M.sub.n(L).sub.m  (1)

[0062] In formula (1), M represents Fe, Co, or Ni with an oxidation number of 0, L represents an isocyanide ligand represented by formula (2) below, n represents an integer of 1 to 8, and m represents an integer of 2 to 12.

(CN).sub.x—R.sup.1  (2)

[0063] In formula (1), as mentioned above, n represents 1 to 4, and m represents 2 to 10; from the viewpoints of the stability of the complex and catalytic activity, it is preferable that, in the case where n is 1, m be 2, 4, or 5; in the case where n=2 to 4, m be an integer of 6 to 10; in the case where n=8, m be 12; it is more preferable that, in the case where M is Fe, n be 1 and m be 5; in the case where M is Co, n be 2 and m be 8; in the case where M is Ni, n be 1 and m be 2 or 4, or n be 3, 4, or 8 and m be 4, 6, 7, or 12.

[0064] In formula (2), R.sup.1 represents a monovalent to trivalent organic group that has 1 to 30 carbon atoms and is optionally substituted with a halogen atom and in which one or more atoms selected from oxygen, nitrogen, sulfur, and silicon are optionally interposed, and x represents an integer of 1 to 3.

[0065] Specific examples of the halogen atom include fluorine, chlorine, bromine, and iodine.

[0066] The monovalent to trivalent organic group having 1 to 30 carbon atoms is not particularly limited, but is preferably a monovalent to trivalent hydrocarbon group having 1 to 30 carbon atoms.

[0067] Examples of monovalent hydrocarbon groups include alkyl, alkenyl, alkynyl, aryl, alkyl aryl, and aralkyl groups.

[0068] The alkyl groups may be straight, branched or cyclic, is preferably 1 to 20, more preferably 1 to 10 alkyl group. Examples include straight or branched alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, and n-eicosanyl; and cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, norbornyl, and adamantyl.

[0069] The alkenyl group is preferably an alkenyl group having 2 to 20 carbon atoms, and examples include ethenyl, n-1-propenyl, n-2-propenyl, 1-methylethenyl, n-1-butenyl, n-2-butenyl, n-3-butenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1-ethylethenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, n-1-pentenyl, n-1-decenyl, and n-1-eicosenyl.

[0070] The alkynyl group is preferably an alkynyl group having 2 to 20 carbon atoms, and examples include ethynyl, n-1-propynyl, n-2-propynyl, n-1-butynyl, n-2-butynyl, n-3-butynyl, 1-methyl-2-propynyl, n-1-pentynyl, n-2-pentynyl, n-3-pentynyl, n-4-pentynyl, 1-methyl-n-butynyl, 2-methyl-n-butynyl, 3-methyl-n-butynyl, 1,1-dimethyl-n-propynyl, n-1-hexynyl, n-1-decynyl, n-1-pentadecynyl, and n-1-eicosynyl.

[0071] The aryl or alkylaryl group is preferably an aryl group having 6 to 20 carbon atoms or an alkylaryl group having 7 to 20 carbon atoms, and specific examples include phenyl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, o-biphenylyl, m-biphenylyl, p-biphenylyl, tolyl, 2,6-dimethylphenyl, 2,6-diisopropylphenyl, a mesityl group, and the like.

[0072] The aralkyl group is an arylalkyl group preferably having 7 to 30 carbon atoms and more preferably having 7 to 20 carbon atoms, and specific examples include benzyl, phenylethyl, phenylpropyl, naphthylmethyl, naphthylethyl, a naphthylpropyl group, and the like.

[0073] Suitable divalent hydrocarbon groups include alkylene, arylene and aralkylene groups.

[0074] The alkylene groups may be straight, branched or cyclic ones, preferably alkylene groups having 1 to 20 carbon atoms. Examples include straight or branched alkylene groups such as methylene, ethylene, propylene, trimethylene, n-butylene, isobutylene, s-butylene, n-octylene, 2-ethylhexylene, n-decylene, n-undecylene, n-dodecylene, n-tridecylene, n-tetradecylene, n-pentadecylene, n-hexadecylene, n-heptadecylene, n-octadecylene, n-nonadecylene, and n-eicosanylene; and cycloalkylene groups such as 1,4-cyclohexylene.

[0075] Examples of the arylene group include o-phenylene, m-phenylene, p-phenylene, 1,2-naphthylene, 1,8-naphthylene, 2,3-naphthylene, and 4,4′-biphenylene.

[0076] Examples of the aralkylene group include —(CH.sub.2).sub.y—Ar— wherein Ar is an arylene group having 6 to 20 carbon atom and y is an integer of 1 to 10, —Ar—(CH.sub.2).sub.y— wherein Ar and y are as defined above, and —(CH.sub.2).sub.y—Ar—(CH.sub.2).sub.y— wherein Ar is as defined above and y is each independently as defined above.

[0077] Specific examples of the trivalent hydrocarbon group include those represented by the following formulae, but are not limited to these.

##STR00001##

[0078] Specific examples of other organic groups in R.sup.1 above include alkoxy groups such as a methoxy group, an ethoxy group, a propoxy group, and an isopropoxy group; aryloxy groups such as a phenoxy group; alkyl halide groups such as a trifluoromethyl group; alkylamino groups such as a dimethylamino group; ester groups such as a methyl ester and an ethyl ester; a nitro group; a nitrile group; alkyl- or arylsilyl groups such as a trimethylsilyl group and a phenyldimethylsilyl group; alkoxysilyl groups such as a trimethoxysilyl group, a triethoxysilyl group, a dimethoxymethylsilyl group, and a diethoxymethylsilyl group; nitrogen-containing heterocycle-containing groups such as a pyridyl group; sulfur-containing heterocycle-containing groups such as a thienyl group; and the like.

[0079] Among these, R.sup.1 is preferably at least one hydrocarbon group selected from an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an alkylaryl group having 7 to 30 carbon atoms, and is more preferably a t-butyl group, a 1-adamantyl group, a mesityl group, a phenyl group, a 2,6-dimethylphenyl group, and a 2,6-diisopropylphenyl group.

[0080] One or more atoms selected from oxygen, nitrogen, silicon, sulfur, and phosphorus may be interposed in each of the organic groups described above, and each of the organic groups described above may be substituted with a halogen atom.

[0081] x in formula (2) above represents an integer of 1 to 3, and is preferably 1 or 2 and more preferably 1.

[0082] The isocyanide compound represented by formula (2) above may be obtained as a commercially available product, or may be synthesized by a known method. For example, it may be obtained by a method in which a formylated product is obtained from an amine compound and formic acid, and subsequently the formylated product is reacted with phosphoryl chloride in the presence of an organic amine to be turned into an isocyanide (Synthesis Method 1; see Organometallics, 2004, 23, 3976-3981); as a method for obtaining a formylated product under mild conditions, a formylated product can be obtained by forming acetic formic anhydride from acetic anhydride and formic acid, and reacting the acetic formic anhydride with an amine compound (Synthesis Method 2; see Org. Synth., 2013, 90, 358-366). The obtained formylated product can be turned into an isocyanide by the method described in Synthesis Method 1, which is the same as above.

[0083] The synthesis can be made also by a method in which an amine compound and dichlorocarbene are reacted together to produce an isocyanide, which is a method not involving formylation (Synthesis Method 3; see Tetrahedron Letters, 1972, 17, 1637-1640).

[0084] Examples of the isocyanide compound include alkyl isocyanides such as methyl isocyanide, ethyl isocyanide, n-propyl isocyanide, cyclopropyl isocyanide, n-butyl isocyanide, isobutyl isocyanide, sec-butyl isocyanide, t-butyl isocyanide, n-pentyl isocyanide, isopentyl isocyanide, neopentyl isocyanide, n-hexyl isocyanide, cyclohexyl isocyanide, cycloheptyl isocyanide, 1,1-dimethylhexyl isocyanide, 1-adamantyl isocyanide, and 2-adamantyl isocyanide; aryl isocyanides such as phenyl isocyanide, 2-methylphenyl isocyanide, 4-methylphenyl isocyanide, 2,4-dimethylphenyl isocyanide, 2,5-dimethylphenyl isocyanide, 2,6-dimethylphenyl isocyanide, 2,4,6-trimethylphenyl isocyanide, 2,4,6-tri-t-butylphenyl isocyanide, 2,6-diisopropylphenyl isocyanide, 1-naphthyl isocyanide, 2-naphthyl isocyanide, 2-methyl-1-naphthyl isocyanide; aralkyl isocyanides such as benzyl isocyanide and phenylethyl isocyanide.

[0085] Examples of the diisocyanide compound include 1,2-diisocyanoethane, 1,3-diisocyanopropane, 1,4-diisocyanobutane, 1,5-diisocyanopentane, 1,6-diisocyanohexane, 1,8-diisocyanooctane, 1,12-diisocyanododecane, 1,2-diisocyanocyclohexane, 1,3-diisocyanocyclohexane, 1,4-diisocyanocyclohexane, 1,3-diisocyano-2,2-dimethylpropane, 2,5-diisocyano-2,5-dimethylhexane, 1,2-bis(diisocyanoethoxy)ethane, 1,2-diisocyanobenzene, 1,3-diisocyanobenzene, 1,4-diisocyanobenzene, 1,1′-methylenebis(4-isocyanobenzene), 1,1′-oxybis(4-isocyanobenzene), 3-(isocyanomethyl)benzyl isocyanide, 1,2-bis(2-isocyanophenoxy)ethane, bis(2-isocyanophenyl)phenyl phosphonate, bis(2-isocyanophenyl) isophthalate, bis(2-isocyanophenyl) succinate.

[0086] Examples of the triisocyanide compound include 1,3-diisocyano-2-(isocyanomethyl)-2-methylpropane, 1,5-diisocyano-3-(2-isocyanoethyl)pentane, 1,7-diisocyano-4-(3-isocyanopropyl)heptane, and 3-isocyano-N,N′-bis(3-isocyanopropyl)propane-1-amine.

[0087] A catalyst made of an isocyanide complex represented by formula (1) above can be synthesized by a known method; for example, the synthesis can be made by a method in which an iron, cobalt, or nickel salt and a reducing agent are reacted together in an organic solvent in the presence of an isocyanide compound, or a method in which an iron-, cobalt-, or nickel-carbonyl complex and an isocyanide compound are reacted together in an organic solvent at high temperature under light irradiation or in the presence of a catalyst. The synthesis can be made also by reacting together an iron, cobalt, or nickel complex having a substitutable ligand and an isocyanide compound in an organic solvent.

[0088] The synthesis can be made also by reacting together an ate-type iron-, cobalt-, or nickel-isocyanide complex and an oxidizing agent in an organic solvent.

[0089] The iron, cobalt, or nickel salt mentioned above is not particularly limited, but is preferably a halide of Cl, Br, I, or the like, or a carboxylate such as acetate, and is more preferably a halide of Cl, Br, I, or the like, in view of reactivity with a reducing agent.

[0090] Specific examples of the iron salt include iron halides such as FeCl.sub.2, FeBr.sub.2, FeCl.sub.3, FeBr.sub.3, and FeI.sub.3; iron carboxylates such as Fe(OAc).sub.2, Fe(stearate).sub.2, and Fe(stearate).sub.3; and the like.

[0091] Specific examples of the cobalt salt include cobalt halides such as CoCl.sub.2, CoBr.sub.2, and CoI.sub.2; cobalt carboxylates such as Co(OAc).sub.2, Co(OBz).sub.2, Co(2-ethylhexanoate).sub.2, and Co(stearate).sub.2; and the like.

[0092] Specific examples of the nickel salt include nickel halides such as NiCl.sub.2, NiBr.sub.2, and NiI.sub.2; nickel carboxylates such as Ni(OAc).sub.2; and the like.

[0093] Specific examples of the iron-, cobalt-, or nickel-carbonyl complex mentioned above include Fe(CO).sub.5, Fe.sub.3(CO).sub.12, Co.sub.2(CO).sub.8, Ni(CO).sub.4, and the like.

[0094] As the substitutable ligand, olefin compounds such as 1,5-cyclooctadiene and butadienes; phosphorus ligands such as trimethylphosphine; and the like are given.

[0095] The reducing agent mentioned above is desirably a strong reducing agent that can reduce a metal in an iron, cobalt, or nickel salt up to zero-valence; for example, is preferably a reducing agent having an oxidation-reduction potential, with ferrocene as a standard, of less than or equal to −2.0 V in Non-Patent Document, Chem. Rev. 1996, 96, 887-910, and is particularly preferably a reducing agent having an oxidation-reduction potential of less than or equal to −2.3 V.

[0096] Specific examples include alkali metals such as sodium and potassium; alkali metal alloys such as sodium-potassium and sodium amalgam; alkali metal naphthalenide such as potassium naphthalenide; and the like, but are not limited to these.

[0097] Each of these alkali metals and alkali metal alloys may be one supported by a solid substance; examples include sodium, potassium, sodium-potassium alloy, or the like supported by silica, alumina, graphite, titanium oxide, zeolite, zinc oxide, cerium oxide, or polystyrene; among these, potassium-carrying graphite (hereinafter, abbreviated as KC.sub.8) is preferable from the viewpoint of reactivity, and sodium-carrying silica (Stage 1 or 2) is preferable in terms of low risk of ignitability etc. from the viewpoint of safety.

[0098] An alkali metal supported by any of these solid substances may be obtained as, for example, one synthesized by a conventionally known method such as a method described in JP 5048503B2, or may be obtained as a commercially available product, examples of which include KC.sub.8(manufactured by Strem Chemicals, Inc.), Na silica gel (manufactured by Aldrich Corporation, Stage I), Na silica gel (manufactured by Aldrich Corporation, Stage II), NaK.sub.2 silica gel (manufactured by Aldrich Corporation, Stage I), and the like.

[0099] The ate-type iron-, cobalt-, or nickel-isocyanide complex mentioned above is generally known as an ionic complex in which an iron-, cobalt-, or nickel-isocyanide complex is further reduced, and Na[Co(2,6-dimesityl isocyanide).sub.4] described in Non-Patent Document 51 and the like are known.

[0100] Ferrocenium triflate or the like is given as an oxidizing agent in the case where the synthesis is made by using an ate-type iron-, cobalt-, or nickel-isocyanide complex.

[0101] The isocyanide complex represented by formula (1) of the present invention is not particularly limited, and examples include the following.

[0102] Specific examples of iron-isocyanide complexes include Fe(CNMe).sub.5, Fe(CNEt).sub.5, Fe(CN.sup.nPr).sub.5, Fe(CN.sup.iPr).sub.5, Fe(CN.sup.nBu).sub.5, Fe(CN.sup.tBu).sub.5, Fe(CNCy).sub.5, Fe(CNAd).sub.5, Fe(CNCF.sub.3).sub.5, Fe(CNPh).sub.5, Fe(CNXylyl).sub.5, Fe(CNMes).sub.5, Fe(N.sub.2)[CN-(2,6-bismesitylphenyl)].sub.4, Fe[CN-(2-methyl-6-chlorophenyl)].sub.5, Fe[CN-(3,5-dimethoxyphenyl)].sub.5, Fe.sub.2(CNEt).sub.9, and the like.

[0103] Specific examples of cobalt-isocyanide complexes include Co.sub.2(CN.sup.tBu).sub.8, Co.sub.2(CNCy).sub.8, Co.sub.2(CNAd).sub.8, Co.sub.2(CNPh).sub.8, Co.sub.2(CNXylyl).sub.8, Co.sub.2(CNMes).sub.8, Co.sub.2[CN-(2-methyl-6-chlorophenyl)].sub.8, Co.sub.2[CN-(3,5-dimethoxyphenyl)].sub.8, Co[CN-(2,6-bismesitylphenyl)].sub.4, and the like.

[0104] Specific examples of nickel-isocyanide complexes include Ni(CNMe).sub.4, Ni(CNEt).sub.4, Ni(CN.sup.tBu).sub.4, Ni.sub.2(CN.sup.tBu).sub.4, Ni.sub.3(CN.sup.tBu).sub.6, Ni(CNCy).sub.4, Ni(CNPh).sub.4, Ni(CNMes).sub.4, Ni(CNXylyl).sub.4, Ni[CN-(4-MeOC.sub.6H.sub.4)].sub.4, Ni[CN-(4-NO.sub.2C.sub.6H.sub.4)].sub.4, Ni(CNC.sub.6F5).sub.4, Ni.sub.4(CN.sup.tBu).sub.6, Ni.sub.4(CN.sup.tBu).sub.7, Ni.sub.4(CNMe)(CN.sup.tBu).sub.6, Ni.sub.4(CNCy).sub.7, Ni.sub.8(CN.sup.iPr).sub.12, and the like.

[0105] In the above, .sup.nPr represents a n-propyl group, .sup.iPr an isopropyl group, .sup.nBu a n-butyl group, .sup.tBu a t-butyl group, Cy a cyclohexylyl group, Ad an adamantyl group, Ph a phenyl group, Mes a mesityl group, and Xylyl a 2,6-dimethylphenyl group.

[0106] When performing reaction using the isocyanide complex of the present invention as a catalyst, the amount of the catalyst used is not particularly limited; however, in view of obtaining the desired product with good yield by progressing reaction under mild conditions of approximately 20 to 100° C., it is preferable that more than or equal to 0.001 mol % of the isocyanide complex be used relative to 1 mol of a compound that is a substrate, it is more preferable that more than or equal to 0.01 mol % be used, and it is even more preferable that more than or equal to 0.05 mol % be used. On the other hand, the upper limit of the amount of the isocyanide complex used is not particularly set, but is approximately 10 mol % relative to 1 mol of the substrate and is preferably 5 mol %, from the economic point of view.

[0107] In the reaction using the catalyst of the present invention, a known two-electron donating ligand may be used in combination to the extent that the activity etc. of the catalyst are not impaired. The two-electron donating ligand is not particularly limited, but is preferably a ligand other than a carbonyl group, such as an ammonia molecule, an ether compound, an amine compound, a phosphine compound, a phosphite compound, or a sulfide compound.

[0108] The isocyanide compound may be further added to the extent that the activity etc. thereof are not impaired, and the addition amount in this case is preferably approximately 0.1 to 5 molar equivalents relative to the catalyst of the present invention.

[0109] The conditions of reaction using the catalyst of the present invention are not particularly limited; usually, the reaction temperature is approximately 10 to 100° C., and preferably 20 to 80° C., and the period of reaction is approximately 1 to 48 hours.

[0110] The reaction may be performed without a solvent, or may use an organic solvent as necessary.

[0111] In the case where an organic solvent is used, examples of the kind include aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, cyclopentyl methyl ether, tetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylenes, and mesitylene; and the like.

[0112] In the case where an organic solvent is used, the concentration of the catalyst is preferably 0.01 to 10 M and more preferably 0.1 to 5 M as molar concentration (M), in view of catalytic activity and economical efficiency.

[0113] The catalyst of the present invention may be used as a catalyst for hydrosilylation reaction or hydrogenation reaction on an aliphatic unsaturated bond or hydrosilane reduction reaction on a carbon-oxygen unsaturated bond or a carbon-nitrogen unsaturated bond.

[0114] In the reaction using the catalyst of the present invention, all the components may be collectively added, or components may be added in units of several components.

[0115] By using the catalyst of the present invention for hydrosilylation reaction, a product of hydrosilylation reaction between an aliphatic unsaturated bond-containing compound and a Si—H bond-containing compound is obtained.

[0116] As the use ratio between the aliphatic unsaturated bond-containing compound and the Si—H bond-containing compound in hydrosilylation reaction, the molar ratio of aliphatic unsaturated bonds/Si—H bonds is 1/10 to 10/1, preferably 1/5 to 5/1, and more preferably 1/3 to 3/1.

[0117] Specific examples of the aliphatic unsaturated bond-containing compound include the following.

(1) Carbon-Carbon Unsaturated Bond-Containing Hydrocarbon Compounds

[0118] Alkenes such as ethylene, propylene, butylene, isobutylene, hexenes, octenes, decenes, dodecenes, n-hexadecene, isohexadecene, n-octadecene, isooctadecene, norbornene, and trifluoropropene; alkynes such as ethyne, propyne, butynes, pentynes, hexynes, octynes, decynes, dodecynes, hexadecynes, and octadecynes; and aromatic group-containing alkenes such as styrene, 2-methylstyrene, 4-chlorostyrene, 4-methoxystyrene, α-methylstyrene, 4-methyl-α-methylstyrene, and allylbenzene.

(2) Allyl Ether Compounds

[0119] Allyl glycidyl ether, allyl glycol, allyl benzyl ether, diethylene glycol monoallyl ether, diethylene glycol allyl methyl ether, polyoxyethylene monoallyl ether, polyoxypropylene monoallyl ether, poly(oxyethylene-oxypropylene) monoallyl ether, polyoxyethylene diallyl ether, polyoxypropylene diallyl ether, poly(oxyethylene-oxypropylene) diallyl ether, and the like.

(3) Nitrogen-Containing Alkene Compounds

[0120] Allylamine, N,N-dimethylallylamine, N,N-diethylallylamine, N,N-di(n-propyl)allylamine, N,N-diisopropylallylamine, N,N-di(n-butyl)allylamine, N,N-diisobutylallylamine, N-t-butylallylamine, N-allylcyclohexylamine, N-allylmorpholine, N,N-diallylamine, triallylamine, N-allylaniline, N-vinylcarbazole, N-vinylformamide, N-vinylacetamide, N-vinylpyrrolidone, N-vinylphthalimide, and the like.

(4) Carbon-Carbon Unsaturated Bond-Containing Silane Compounds

[0121] Trimethylvinylsilane, triethylvinylsilane, trimethoxyvinylsilane, triethoxyvinylsilane, dimethoxymethylvinylsilane, diethoxymethylvinylsilane, methoxydimethylvinylsilane, ethoxydimethylvinylsilane, trimethoxyallylsilane, triethoxyallylsilane, triisopropoxyvinylsilane, phenyldimethoxyvinylsilane, phenyldiethoxyvinylsilane, diphenylmethoxyvinylsilane, diphenylethoxyvinylsilane, triphenylvinylsilane, triphenylvinylsilane, and the like.

(5) Carbon-Carbon Unsaturated Bond-Containing Siloxane Compounds

[0122] Pentamethylvinyldisiloxane, tetramethyldivinyldisiloxane, heptamethylvinyltrisiloxane, dimethyldiphenyldivinyldisiloxane, dimethylvinylsiloxy group-end-capped dimethylpolysiloxane, and a dimethylvinylsiloxy group-end-capped (dimethylsiloxane-diphenylsiloxane) copolymer. A trimethylsiloxy group-end-capped (dimethylsiloxane-methylvinylsiloxane) copolymer, a trimethylsiloxy group-end-capped (dimethylsiloxane-diphenylsiloxane-methylvinylsiloxane) copolymer, a dimethylvinylsiloxy group-end-capped (dimethylsiloxane-methylvinylsiloxane) copolymer, a dimethylvinylsiloxy group-end-capped (dimethylsiloxane-methylvinylsiloxane-diphenylsiloxane) copolymer, a hydroxy group-end-capped (dimethylsiloxane-methylvinylsiloxane) copolymer, α-vinyldimethylpolysiloxane, and the like.

[0123] In the aliphatic unsaturated bond-containing compound mentioned above, an unsaturated bond may exist at a molecular end or may exist in the interior, or a plurality of unsaturated bonds may exist in the molecule like in hexadienes and octadienes.

[0124] Also an alkene compound having a sulfide group like those shown below may be used as the aliphatic unsaturated bond-containing compound. In this case, unlike a silicon compound in which silicon is bonded to carbon at an end of an alkene, which is known in the case where a platinum catalyst is used, isomerization reaction of an alkene occurs, and a silicon compound in which silicon is bonded onto carbon adjacent to the sulfur element is obtained selectively.

(6) Alkene Compounds Having Sulfide Group

[0125] Methyl vinyl sulfide, ethyl vinyl sulfide, n-propyl vinyl sulfide, isopropyl vinyl sulfide, n-butyl vinyl sulfide, phenyl vinyl sulfide, benzyl vinyl sulfide, methyl allyl sulfide, ethyl allyl sulfide, n-propyl allyl sulfide, isopropyl allyl sulfide, n-butyl allyl sulfide, isobutyl allyl sulfide, phenyl allyl sulfide, benzyl allyl sulfide, allyl (n-propyl) disulfide, diallyl sulfide, diallyl disulfide, and the like.

Examples of the Si—H Bond-Containing Compound Include the Following Silanes and Siloxanes

(1) Silanes

[0126] Trimethoxysilane, triethoxysilane, triisopropoxysilane, dimethoxymethylsilane, diethoxymethylsilane, dimethoxyphenylsilane, diethoxyphenylsilane, methoxydimethylsilane, ethoxydimethylsilane, triphenylsilane, diphenyldisilane, phenyltrisilane, diphenylmethylsilane, phenyldimethylsilane, diphenylmethoxysilane, diphenylethoxysilane, and the like.

(2) Siloxanes

[0127] Pentamethyldisiloxane, tetramethyldisiloxane, heptamethyltrisiloxane, octamethyltetrasiloxane, dimethyl hydrogen siloxy group-end-capped dimethylpolysiloxane, dimethyl hydrogen siloxy group-end-capped methyl hydrogen polysiloxane, trimethylsiloxy group-end-capped methyl hydrogen polysiloxane, a dimethyl hydrogen siloxy group-end-capped (dimethylsiloxane-diphenylsiloxane) copolymer, a trimethylsiloxy group-end-capped (dimethylsiloxane-methylhydrosiloxane) copolymer, a trimethylsiloxy group-end-capped (dimethylsiloxane-diphenylsiloxane-methylhydrogensiloxane) copolymer, a dimethyl hydrogen siloxy group-end-capped (dimethylsiloxane-methylhydrogensiloxane) copolymer, a dimethyl hydrogen siloxy group-end-capped (dimethylsiloxane-methylhydrogensiloxane-diphenylsiloxane) copolymer, a hydroxy group-end-capped (dimethylsiloxane-methylhydrogensiloxane) copolymer, dimethyl hydrogen siloxy group-one-end-capped dimethylpolysiloxane, and the like.

[0128] Further, by reacting together an aliphatic unsaturated bond-containing compound and a hydrogen molecule in the presence of the catalyst of the present invention, a corresponding compound having a saturated bond is obtained.

[0129] Specific examples of the aliphatic unsaturated bond-containing compound include compounds similar to those given as examples in hydrosilylation reaction mentioned above.

[0130] As a means for introducing a hydrogen molecule into a reaction system in hydrogenation reaction, introduction may be made while gas containing hydrogen molecules is caused to flow or bubble in a reactor, or reaction may be performed in a pressure resistant vessel in which gas containing hydrogen molecules is enclosed. The pressure at this time is not particularly limited, but is preferably 0.1 to 3 MPa and more preferably 0.1 to 2 MPa from the viewpoint of safety.

[0131] Further, a product of hydrosilane reduction reaction between a compound having a carbon-oxygen unsaturated bond or a carbon-nitrogen unsaturated bond and a Si—H bond-containing compound is obtained in the presence of the catalyst of the present invention.

[0132] In this case, the use ratio between the compound having a carbon-oxygen unsaturated bond or a carbon-nitrogen unsaturated bond and the Si—H bond-containing compound is not particularly limited; however, as the molar ratio, (carbon-oxygen unsaturated bonds or carbon-nitrogen unsaturated bonds)/(Si—H bonds) is preferably 1/10 to 1/1, more preferably 1/5 to 1/1, and still more preferably 1/3 to 1/1.

[0133] As the Si—H bond-containing compound used in hydrosilane reduction reaction of a compound having a carbon-oxygen unsaturated bond or a carbon-nitrogen unsaturated bond of the present invention, compounds similar to those shown as examples in hydrosilylation reaction mentioned above are given; in view of reactivity and economical efficiency, among them, aryl group-containing silanes such as phenylsilane, diphenylsilane, and dimethylphenylsilane; a siloxane containing Si—H groups adjacent via an oxygen atom, such as 1,1,3,3-tetramethyldisiloxane, trimethylsiloxy group-end-capped methyl hydrogen polysiloxane, and dimethyl hydrogen siloxy group-end-capped methyl hydrogen polysiloxane, are preferable, and 1,1,3,3-tetramethyldisiloxane, 1,1,1,3,3-pentamethyldisiloxane, 1,1,1,3,5,5,5-heptamethyltrisiloxane, trimethylsiloxy group-end-capped methyl hydrogen polysiloxane, and dimethyl hydrogen siloxy group-end-capped methyl hydrogen polysiloxane are more preferable.

[0134] As the compound having a carbon-oxygen unsaturated bond or a carbon-nitrogen unsaturated bond that can be used for hydrosilane reduction reaction, a compound having an aldehyde, ketone, amide, or nitrile group, and the like are given; by reacting any of these compounds with a silane or a siloxane containing a Si—H group in the presence of the catalyst of the present invention and performing known post-treatment, the compound can be turned into a respective corresponding amine or alcohol compound.

[0135] Specific examples of the compound having a carbon-oxygen unsaturated bond or a carbon-nitrogen unsaturated bond include acetophenone, N,N-dimethylbenzamide, acetonitrile, and the like.

EXAMPLES

[0136] Synthesis Examples, Examples and Comparative Examples are given below by way of illustration and not by way of limitation.

[0137] All solvents were deoxygenated and dehydrated by well-known methods before they were used in the preparation of catalysts.

[0138] The catalysts obtained were stored in a nitrogen gas atmosphere at 25° C. until they were used in reaction.

[0139] Hydrosilylation reaction and solvent purification were always carried out in an inert gas atmosphere. The solvents and other ingredients were purified, dried and deoxygenated by well-known methods before they were used in various reactions.

[0140] The measurement of .sup.1H-NMR was performed using JNM-ECA600 and JNM-LA400 manufactured by JEOL Ltd, and IR measurement was performed using FT/IR-550 manufactured by JASCO Corporation.

[0141] In the chemical structure formulae shown below, hydrogen atoms are omitted in accordance with common expression.

[Synthesis Example 1] Synthesis of Cobalt Isocyanide Complex Co.SUB.2.(CN.SUP.t.Bu).SUB.8

[0142] Cobalt iodide (0.31 g, 1.0 mmol), tetrahydrofuran (hereinafter, abbreviated as THF) (15 mL), t-butyl isocyanide (0.33 g, 4.0 mmol), and KC.sub.8(manufactured by Strem Chemicals, Inc., 0.27 g, 2.0 mmol) were added in this order to a reactor, and stirring was performed at 25° C. for 12 hours. After that, the reaction solution was subjected to celite filtration, and the solvent of the filtrate was distilled under reduced pressure. The resulting dried substance was dissolved in pentane (approximately 40 mL), and the insoluble matter was removed by celite filtration. The filtrate was cooled to −35° C. to perform recrystallization; thus, Co.sub.2(CN.sup.tBu).sub.8 was obtained (0.24 g, 61%).

[0143] .sup.1H-NMR (600 MHz, C.sub.6D6) δ: 1.44 (s, 72H).

[0144] IR (ATR): v=1666 (CN (bridge)), 2093, 1977, 1942 (CN (terminal)) cm.sup.−1

[0145] Anal. Calcd. for C.sub.40H.sub.72N.sub.8Co.sub.2:

[0146] C: 61.36; H: 9.27; N: 14.31; Found: C: 61.06; H: 9.52; N: 14.05.

[Synthesis Example 2] Synthesis of Cobalt Isocyanide Complex Co.SUB.2.(CNAd).SUB.8

[0147] 0.31 g (1.0 mmol) of cobalt iodide, 0.65 g (4.0 mmol) of 1-isocyanoadamantane (hereinafter, abbreviated as CNAd), THF (15 mL), and KC.sub.8(0.27 g, 2.0 mmol) were added in this order to a reactor, and stirring was performed at 25° C. for 12 hours. After that, the reaction solution was subjected to celite filtration, and the solvent of the filtrate was distilled under reduced pressure. The resulting dried substance was dissolved in toluene (approximately 20 ml), and celite filtration was performed again. The solvent of the filtrate was distilled under reduced pressure, and then the dried substance was washed with a small amount of benzene (approximately 3 ml); thus, Co.sub.2(CNAd).sub.8 was obtained (0.33 g, 47%).

[0148] .sup.1H-NMR (396 MHz, C.sub.6D6) δ:

[0149] 2.32 (s, 48H), 2.06 (s, 24H), 1.71 (d, J=10.3, 24H),

[0150] 1.58 (d, J=10.3, 24H).

[0151] IR (ATR): v=1647 (CN (bridge)), 2101, 2000, 1954 (CN (terminal)) cm.sup.−1

[0152] Anal. Calcd. for C.sub.88H.sub.120N.sub.8Co.sub.2:

[0153] C: 75.08; H: 8.59; N: 7.96; Found: C: 75.16; H: 8.62; N: 7.46.

[Synthesis Example 3] Synthesis of Cobalt Isocyanide Complex Co.SUB.2.(CNMes).SUB.8

[0154] Cobalt iodide (13 mg, 0.10 mmol), mesityl isocyanide (58 mg, 0.40 mmol), THF (3 mL), and KC.sub.8(27 mg, 0.20 mmol) were added in this order to a reactor, and stirring was performed at 25° C. for 12 hours. After that, the reaction solution was subjected to celite filtration, and the solvent of the filtrate was distilled under reduced pressure. The resulting dried substance was dissolved in toluene (approximately 3 mL), and the insoluble matter was removed by celite filtration. Pentane (approximately 3 mL) was slowly added from above the filtrate to perform recrystallization; thus, a cobalt isocyanide complex of Co.sub.2(CNMes).sub.8 was obtained (42 mg, 66%).

[0155] .sup.1H-NMR (396 MHz, C.sub.6D6) δ:

[0156] 6.60 (s, 12H), 6.58 (s, 4H), 2.46 (s, 36H), 2.42 (s, 12H), 2.05 (s, 18H), 2.03 (s, 6H).

[0157] IR (ATR): v=1669 (CN (bridge)), 2063, 2026, 1954 (CN (terminal)) cm.sup.−1

[0158] Anal. Calcd. for C.sub.80H.sub.88N.sub.8Co.sub.2:

[0159] C: 75.10; H: 6.93; N: 8.60; Found: C: 75.21; H: 6.90; N: 8.60.

[Synthesis Example 4] Synthesis of Iron Isocyanide Complex Fe(CN.SUP.t.Bu).SUB.5

[0160] Iron bromide (22 mg, 0.10 mmol), THF (3 mL), t-butyl isocyanide (42 mg, 0.50 mmol), and KC.sub.8(27 mg, 0.20 mmol) were added in this order to a reactor, and stirring was performed at 25° C. for 12 hours. After that, the reaction solution was subjected to celite filtration, and the solvent of the filtrate was distilled under reduced pressure. The resulting dried substance was dissolved in pentane (approximately 4 mL), and the insoluble matter was removed by celite filtration. The filtrate was cooled to −35° C. to perform recrystallization; thus, Fe(CN.sup.tBu).sub.5 was obtained (30 mg, 63%).

[0161] .sup.1H-NMR (600 MHz, C.sub.6D6) δ: 1.29 (s, 45H).

[0162] IR (ATR): v=2119, 2000, 1943, 1826 (CN) cm.sup.−1

[Synthesis Example 5] Synthesis of Iron Isocyanide Complex Fe(CNAd).SUB.5 .Using Iron Bromide and KC.SUB.8

[0163] Iron bromide (216 mg, 1.0 mmol), THF (20 mL), adamantyl isocyanide (806 mg, 5.0 mmol), and KC.sub.8(manufactured by Strem Chemicals, Inc., 270 mg, 2.0 mmol) were added in this order to a reactor, and stirring was performed at 25° C. for 12 hours. After that, the reaction solution was subjected to celite filtration, and the solvent of the filtrate was distilled under reduced pressure. The resulting dried substance was dissolved in benzene (approximately 5 mL), and the insoluble matter was removed by celite filtration. Pentane was added to the filtrate, and then cooling was performed to −35° C. to perform recrystallization; thus, Fe(CNAd).sub.5 was obtained (601 mg, yield: 70%).

[0164] .sup.1H-NMR (396 MHz, C.sub.6D6) δ:

[0165] 2.15 (s, 30H), 1.88 (s, 15H), 1.50 (d, J=11.5, 15H),

[0166] 1.42 (d, J=11.5, 15H).

[0167] IR (ATR): v=2106 (CN) cm.sup.−1

[Synthesis Example 6] Synthesis of Nickel Isocyanide Complex Ni (CNtBu).SUB.4 .Using Nickel Bromide (Dimethoxyethane Adduct) and KC.SUB.8

[0168] Nickel bromide (a dimethoxyethane adduct) (31 mg, 0.1 mmol), THF (3 mL), t-butyl isocyanide (0.33 g, 0.4 mmol), and KC.sub.8(270 mg, 2.0 mmol) were added in this order to a reactor, and stirring was performed at room temperature for 30 minutes. After that, the reaction solution was subjected to celite filtration, and the solvent of the filtrate was distilled under reduced pressure. The resulting dried substance was dissolved in benzene (approximately 5 mL), and the insoluble matter was removed by celite filtration. Ether was added to the filtrate, and then cooling was performed to −35° C. to perform recrystallization; thus, Ni(CN.sup.tBu).sub.4 was obtained (21 mg, yield: 54%).

[0169] .sup.1H-NMR (396 MHz, C.sub.6D6) δ: 1.09 (s, 36H).

[0170] IR (ATR): v=2002 (CN) cm.sup.−1

[0171] Hydrosilylation Reaction Using Alkene as Substrate

[Example 1] Hydrosilylation Reaction by 1,1,1,3,3-pentamethyldisiloxane of α-methylstyrene Using Co.SUB.2.(CN.SUP.t.Bu).SUB.8 .as Catalyst

[0172] Co.sub.2(CN.sup.tBu).sub.8 obtained in Synthesis Example 1 (3.4 mg, 0.005 mmol), α-methylstyrene (129 μL, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 25° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.94 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 1.

[0173] .sup.1H-NMR (396 MHz, CDCl.sub.3) δ:

[0174] 7.27 (t, J=6.8, 2H), 7.21 (d, J=6.8, 2H), 7.15 (t, J=6.8, 1H),

[0175] 2.91 (sext, J=6.8, 1H), 1.28 (d, J=6.8, 3H), 0.90-0.98 (m, 2H),

[0176] 0.05 (s, 9H), −0.05 (s, 3H), −0.07 (s, 3H).

Examples 2 and 3

[0177] Reaction was performed in a similar manner to Example 1 except that, in place of Co.sub.2(CN.sup.tBu).sub.8, the cobalt-isocyanide complexes written in Table 1 (each 0.005 mmol) were used as catalysts. The results are shown in Table 1 below.

Comparative Example 1

Hydrosilylation Reaction by 1,1,1,3,3-Pentamethyldisiloxane of α-Methylstyrene Using, as Catalyst, Composition Consisting of Cobalt Pivalate, CNAd, and diethoxymethylsilane

[0178] 3 mg (0.01 mmol) of cobalt pivalate, 5 mg (0.03 mmol) of CNAd, and 100 μL of THF were added to a reactor, and were dissolved. 5.3 mg (0.04 mmol) of diethoxymethylsilane was added to the reactor, and stirring was performed at 25° C. for 1 hour. After that, α-methylstyrene (129 μL, 1.0 mmol) and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added, and stirring was performed at 25° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.94 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 1.

TABLE-US-00003 TABLE 1 Conversion Yield Catalyst (%) (%) Example 1 Co.sub.2(CN.sup.tBu).sub.8 >99 >99 Example 2 Co.sub.2(CNAd).sub.8 >99 >99 Example 3 Co.sub.2(CNMes).sub.8 >99 >99 Comparative Example 1 cobalt pivalate / CNAd /   10   10 diethoxymethylsilane

[Example 4] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of α-methylstyrene using Co.SUB.2.(CNAd).SUB.8 .as catalyst

[0179] Co.sub.2(CNAd).sub.8 obtained in Synthesis Example 2 (6.4 mg, 0.0005 mmol), α-methylstyrene (1.29 mL, 10 mmol), and 1,1,1,3,3-pentamethyldisiloxane (2.54 mL, 13 mmol) were added to a reactor, and stirring was performed at 80° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.94 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 2.

Comparative Example 2

Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of α-methylstyrene using Co.SUB.2.(CO).SUB.8 .as catalyst

[0180] Co.sub.2(CO).sub.8 (1.7 mg, 0.0005 mmol), α-methylstyrene (1.29 mL, 10 mmol), and 1,1,1,3,3-pentamethyldisiloxane (2.54 mL, 13 mmol) were added to a reactor, and stirring was performed at 80° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.94 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 2.

TABLE-US-00004 TABLE 2 Conversion Yield Catalyst (%) (%) Example 4 Co.sub.2(CNAd).sub.8 >99 >99 Comparative Example 2 Co.sub.2(CO).sub.8   88   88

[Example 5] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of styrene using Fe(CN.SUP.t.Bu).SUB.5 .as catalyst

[0181] Fe(CN.sup.tBu).sub.5 obtained in Synthesis Example 4 (4.7 mg, 0.01 mmol), styrene (114 μL, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 25° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.90 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 3.

[0182] .sup.1H-NMR (396 MHz, CDCl.sub.3) δ:

[0183] 7.24-7.29 (m, 2H), 7.13-7.22 (m, 3H), 2.61-2.68 (m, 2H),

[0184] 0.86-0.92 (m, 2H), 0.08 (s, 9H), 0.07 (s, 6H).

[Example 6] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of 1-octene using Co.SUB.2.(CNMes).SUB.8 .as catalyst

[0185] Co.sub.2(CNMes).sub.8 obtained in Synthesis Example 3 (6.4 mg, 0.005 mmol), 1-octene (157 μL, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 25° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.50 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 3.

[0186] .sup.1H-NMR (396 MHz, CDCl.sub.3) δ:

[0187] 1.21-1.37 (m, 12H), 0.88 (t, J=6.8, 3H), 0.50 (m, 2H), 0.06 (s, 9H), 0.03 (s, 6H).

[Example 7] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of styrene using Co.SUB.2.(CNMes).SUB.8 .as catalyst

[0188] Co.sub.2(CNMes).sub.8 obtained in Synthesis Example 3 (6.4 mg, 0.005 mmol), styrene (114 μL, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 25° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.90 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 3.

[0189] .sup.1H-NMR (396 MHz, CDCl.sub.3) δ:

[0190] 7.24-7.29 (m, 2H), 7.13-7.22 (m, 3H), 2.61-2.68 (m, 2H),

[0191] 0.86-0.92 (m, 2H), 0.08 (s, 9H), 0.07 (s, 6H).

[Example 8] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of allyl glycidyl ether using Co.SUB.2.(CNAd).SUB.8 .as catalyst

[0192] Co.sub.2(CNAd).sub.8 obtained in Synthesis Example 2 (6.4 mg, 0.005 mmol), allyl glycidyl ether (118 μL, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 25° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.51 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 3.

[0193] .sup.1H-NMR (396 MHz, CDCl.sub.3) δ:

[0194] 3.71 (dd, J=11.6, J=3.9, 1H) 3.37-3.51 (m, 3H),

[0195] 3.26 (dt, J=2.9, J=6.3, 1H), 2.62 (t, J=4.4, 1H), 2.62 (q, J=2.9, 1H),

[0196] 1.59-1.65 (m, 2H), 0.49-0.53 (m, 2H), 0.06 (s, 9H).

TABLE-US-00005 TABLE 3 Conversion Yield Alkene Catalyst (%) (%) Example 5 styrene Fe(CN.sup.tBu).sub.5 >99 99 Example 6 1-octene Co.sub.2(CNMes).sub.8 >99 24 Example 7 styrene Co.sub.2(CNMes).sub.8   90 44 Example 8 allyl glycidyl ether Co.sub.2(CNAd).sub.8 >99 90

[Example 9] Hydrosilylation reaction by 1,1,1,3,5,5,5-heptamethyltrisiloxane of α-methylstyrene using Co.SUB.2.(CN.SUP.t.Bu).SUB.8 .as catalyst

[0197] Co.sub.2(CN.sup.tBu).sub.8 obtained in Synthesis Example 1 (3.4 mg, 0.005 mmol), α-methylstyrene (129 μL, 1.0 mmol), and 1,1,1,3,5,5,5-heptamethyltrisiloxane (351 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 80° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.88 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 4.

[0198] .sup.1H-NMR (396 MHz, CDCl.sub.3) δ:

[0199] 7.27 (t, J=6.8, 2H), 7.21 (d, J=6.8,2H), 7.16 (t, J=6.8, 1H),

[0200] 2.92 (sext, J=6.8, 1H), 1.28 (d, J=6.8, 3H), 0.82-0.94 (m, 2H),

[0201] 0.09 (s, 9H), 0.07 (s, 9H), −0.12 (s, 3H).

[Example 10] Hydrosilylation reaction by triethoxysilane of α-methylstyrene using Co.SUB.2.(CNAd).SUB.8 .as catalyst

[0202] Co.sub.2(CNAd).sub.8 obtained in Synthesis Example 2 (6.4 mg, 0.005 mmol), α-methylstyrene (129 μL, 1.0 mmol), and triethoxysilane (213 mg, 1.3 mmol) were added to a reactor, and stirring was performed at 80° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A sextet at 3.00 ppm, which is a signal of protons on carbon adjacent to a phenyl group in the desired product, was observed, and the yield was found. The results are shown in Table 4.

[0203] .sup.1H-NMR (396 MHz, CDCl.sub.3) δ:

[0204] 7.27(t, J=6.8, 2H), 7.21 (d, J=6.8, 2H), 7.15 (t, J=6.8, 1H),

[0205] 3.73 (q, J=6.8, 6H), 2.96 (sext, J=6.8, 1H), 1.31 (d, J=6.8, 3H),

[0206] 1.18 (m, J=6.8, 9H), 1.03 (d, J=6.8, 2H).

[Example 11] Hydrosilylation reaction by diethoxy(methyl)silane of α-methylstyrene using Co.SUB.2.(CN.SUP.t.Bu).SUB.8 .as catalyst

[0207] Co.sub.2(CN.sup.tBu).sub.8 obtained in Synthesis Example 1 (3.4 mg, 0.005 mmol), α-methylstyrene (129 μL, 1.0 mmol), and diethoxy(methyl)silane (175 mg, 1.3 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A sextet at 2.96 ppm, which is a signal of protons on carbon adjacent to a phenyl group in the desired product, was observed, and the yield was found. The results are shown in Table 4.

[0208] .sup.1H-NMR (396 MHz, CDCl.sub.3) δ:

[0209] 7.27 (t, J=6.8, 2H), 7.21 (d, J=6.8, 2H), 7.15 (t, J=6.8, 1H),

[0210] 3.63-3.70 (m, 4H), 3.00 (sext, J=6.8, 1H), 1.32 (d, J=6.8, 3H),

[0211] 1.21 (t, J=6.8, 3H), 1.15 (t, J=6.8, 3H), 1.03 (d, J=6.8, 2H),

[0212] −0.08 (s, 3H).

TABLE-US-00006 TABLE 4 Conversion Yield Silane Catalyst (%) (%) Example 9 1,1,1,3,5,5,5- Co.sub.2(CN.sup.tBu).sub.8 >99 >99 heptamethyltrisiloxane Example 10 triethoxysilane Co.sub.2(CNAd).sub.8   84   45 Example 11 Diethoxy(methyl)silane Co.sub.2(CN.sup.tBu).sub.8 >99   92

[Example 12] Hydrosilylation reaction by polydimethylsiloxane endblocked at both terminals by dimethylhydrogensiloxy groups of allyl glycidyl ether using Co.SUB.2.(CNAd).SUB.8 .as catalyst

[0213] Co.sub.2(CNAd).sub.8 obtained in Synthesis Example 2 (6.4 mg, 0.005 mmol), allyl glycidyl ether (154 μL, 1.3 mmol), and polydimethylsiloxane endblocked at both terminals by dimethylhydrogensiloxy groups (degree of polymerization 18) (0.74 g, 0.50 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.54 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found (yield >99%).

[0214] .sup.1H-NMR (396 MHz, CDCl.sub.3) δ:

[0215] 3.70 (m, 1H), 2.95-2.90 (m, 2H), 3.45 (m, 3H), 3.15 (m, 1H),

[0216] 2.80 (m, 1H), 2.61 (m, 1H), 1.62 (m, 2H), 0.54 (m, 2H), 0.08 (br),

[0217] 0.05 (s), −0.08 (s).

[2] Hydrosilylation Reaction Using Sulfur-Containing Alkene as Substrate

[0218] ##STR00002##

[Example 13] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of ethyl vinyl sulfide using Co.SUB.2.(CN.SUP.t.Bu).SUB.8 .as catalyst

[0219] Co.sub.2(CN.sup.tBu).sub.8 obtained in Synthesis Example 1 (3.4 mg, 0.005 mmol), ethyl vinyl sulfide (88 mg, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 25° C. for 24 hours. After the reaction ended, isolation and purification were performed by silica gel chromatography, and 239 mg of the desired product was obtained. Yields are shown in Table 5.

[0220] .sup.1H-NMR (400 MHz, CDCl.sub.3) δ:

[0221] 0.08 (s, 9H,—SiMe.sub.3), 0.12 (s, 3H), 0.16 (s, 3H), 0.98 (t, J=7.32 Hz, 3H), 1.50-1.65 (m, 3H), 1.68-1.71 (m, 1H), 1.75-1.81 (m, 1H), 2.49 (t, 2H).

[Example 14] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of phenyl vinyl sulfide using Co.SUB.2.(CN.SUP.t.Bu).SUB.8 .as catalyst

[0222] Co.sub.2(CN.sup.tBu).sub.8 obtained in Synthesis Example 1 (6.0 mg, 0.0075 mmol), phenyl vinyl sulfide (68 mg, 0.5 mmol), and 1,1,1,3,3-pentamethyldisiloxane (223 mg, 1.5 mmol) were added to a reactor, and stirring was performed at 25° C. for 24 hours. After the reaction ended, isolation and purification were performed by Kugelrohr distillation, and 129 mg of the desired product was obtained. Yields are shown in Table 5.

[0223] .sup.1H-NMR (400 MHz, CDCl.sub.3)

[0224] δ: 0.11 (s, 9H), 0.18 (s, 3H), 0.20 (s, 3H), 1.31 (d, J=7.73 Hz, 3H),

[0225] 2.54 (q, J=7.09 Hz, 1H), 7.28 (dd, J=7.73, 9.67 Hz, 1H),

[0226] 7.28 (d, J=7.73 Hz, 2H), 7.35 (d, J=9.67 Hz, 2H).

[Example 15] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of methyl allyl sulfide using Co.SUB.2.(CN.SUP.t.Bu).SUB.8 .as catalyst

[0227] Co.sub.2(CN.sup.tBu).sub.8 obtained in Synthesis Example 1 (3.4 mg, 0.005 mmol), methyl allyl sulfide (88 mg, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 25° C. for 24 hours. After the reaction ended, isolation and purification were performed by silica gel chromatography, and 209 mg of the desired product was obtained. Yields are shown in Table 5.

[0228] .sup.1H-NMR (400 MHz, CDCl.sub.3) δ:

[0229] 0.08 (s, 9H), 0.13 (s, 3H), 0.16 (s, 3H), 1.06 (t, J=7.14 Hz, 3H),

[0230] 1.57-1.62 (m, 2H), 1.75-1.81 (m, 1H), 2.09 (s, 3H).

[Example 16] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of n-propyl allyl sulfide using Co.SUB.2.(CN.SUP.t.Bu).SUB.8 .as catalyst

[0231] Co.sub.2(CN.sup.tBu).sub.8 obtained in Synthesis Example 1 (3.4 mg, 0.005 mmol), n-propyl allyl sulfide (116 mg, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 25° C. for 24 hours. After the reaction ended, isolation and purification were performed by silica gel chromatography, and 239 mg of the desired product was obtained. Yields are shown in Table 5.

[0232] .sup.1H-NMR (400 MHz, CDCl.sub.3) δ:

[0233] 0.08 (s, 9H), 0.12 (s, 3H), 0.16 (s, 3H), 0.98 (t, J=7.32 Hz, 3H),

[0234] 1.50-1.65 (m, 3H), 1.68-1.71 (m, 1H), 1.75-1.81 (m, 1H), 2.49 (t, 2H).

[Example 17] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of phenyl allyl sulfide using Co.SUB.2.(CN.SUP.t.Bu).SUB.8 .as catalyst

[0235] Co.sub.2(CN.sup.tBu).sub.8 obtained in Synthesis Example 1 (9.7 mg, 0.0125 mmol), phenyl allyl sulfide (75 mg, 0.5 mmol), and 1,1,1,3,3-pentamethyldisiloxane (127 μL, 0.65 mmol) were added to a reactor, and stirring was performed at 25° C. for 24 hours. After the reaction ended, isolation and purification were performed by Kugelrohr distillation, and 142 mg of the desired product was obtained. Yields are shown in Table 5.

[0236] .sup.1H-NMR (600 MHz, CDCl.sub.3) δ:

[0237] 0.10 (s, 9H), 0.19 (s, 3H), 0.19 (s, 3H), 1.31 (t, J=7.42 Hz, 3H),

[0238] 1.67 (dqd, J=6.04, 7.42, 13.74 Hz, 1H),

[0239] 1.81 (dqd, 6.04, 7.42, 13.74 Hz, 1H), 7.14 (td, J=7.42, 2.75 Hz, 1H),

[0240] 7.25-7.26 (m, 2H), 7.35 (dd, J=8.24, 1.10 Hz, 2H).

[Example 18] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of benzyl allyl sulfide using Co.SUB.2.(CN.SUP.t.Bu).SUB.8 .as catalyst

[0241] Co.sub.2(CN.sup.tBu).sub.8 obtained in Synthesis Example 1 (3.4 mg, 0.005 mmol), benzyl allyl sulfide (164 mg, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 25° C. for 24 hours. After the reaction ended, isolation and purification were performed by Kugelrohr distillation, and 245 mg of the desired product was obtained. Yields are shown in Table 5.

[0242] .sup.1H-NMR (400 MHz, CDCl.sub.3) δ:

[0243] 0.05 (s, 9H), 0.06 (s, 3H), 1.01 (t, J=7.32 Hz, 3H), 1.53-1.62 (m, 1H),

[0244] 1.63-1.67 (m, 1H), 1.69-1.80 (m, 1H), 3.66-3.75 (m, 2H),

[0245] 7.22-7.30 (m, 5H).

Comparative Example 3

Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of methyl allyl sulfide using Co.SUB.2.(CO).SUB.8 .as catalyst

[0246] Co.sub.2(CN.sup.tBu).sub.8 obtained in Synthesis Example 1 (3.4 mg, 0.005 mmol), methyl allyl sulfide (88 mg, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 25° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured; as a result, only the source material was observed, and a product was not seen (a yield of 0%).

TABLE-US-00007 TABLE 5 Isolated Conversion Yield yield Sulfur-containing alkene Product (%) (%) (%) Example 13 [00003] [00004] > 99 > 99 90 Example 14 [00005] [00006] > 99 > 99 90 Example 15 [00007] [00008] > 99 > 99 89 Example 16 [00009] [00010] > 99 > 99 90 Example 17 [00011] [00012] > 99   97 95 Example 18 [00013] [00014] > 99 > 99 92

[3] Hydrosilylation Reaction Using Nitrogen-Containing Alkene as Substrate

[0247] ##STR00015##

[Example 19] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of N-allylaniline using Co.SUB.2.(CNAd).SUB.8 .as catalyst

[0248] Co.sub.2(CNAd).sub.8 obtained in Synthesis Example 2 (6.4 mg, 0.005 mmol), N-allylaniline (133 mg, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 25° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.59 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 6.

[0249] .sup.1H-NMR (400 MHz, CDCl.sub.3) δ:

[0250] 0.07 (s, 15H), 0.59 (m, 2H), 1.63 (m, 2H), 3.10 (q, J=5.8, 2H),

[0251] 3.66 (br, 1H), 6.60 (d, J=7.7, 2H), 6.68 (t, J=7.7, 1H),

[0252] 7.17 (t, J=7.2, 2H).

[Example 20] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of N,N-diethylallylamine using Co.SUB.2.(CNAd).SUB.8 .as catalyst

[0253] Co.sub.2(CNAd).sub.8 obtained in Synthesis Example 2 (6.4 mg, 0.005 mmol), N,N-diethylallylamine (113 mg, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.46 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 6.

[0254] .sup.1H-NMR (400 MHz, CDCl.sub.3) δ:

[0255] 0.03 (s, 9H), 0.04 (s, 3H), 0.05 (s, 3H), 0.46 (m, 2H), 1.02 (t, J=7.4, 6H),

[0256] 1.47 (m, 2H), 2.40 (t, J=8.0, 2H), 2.52 (q, J=7.4, 4H).

[Example 21] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of 9-vinylcarbazole using Co.SUB.2.(CNMes).SUB.8 .as catalyst

[0257] Co.sub.2(CNMes).sub.8 obtained in Synthesis Example 3 (6.4 mg, 0.005 mmol), N-methyl pyrrolidone (100 μL) as a solvent, 9-vinylcarbazole (193 mg, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 25° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 1.16 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 6.

[0258] .sup.1H-NMR (400 MHz, CDCl.sub.3) δ:

[0259] 0.15 (s, 6H), 0.17 (s, 9H), 1.16 (m, 2H), 4.38 (m, 2H),

[0260] 7.23 (t, J=7.7 Hz, 2H), 7.39 (d, J=7.7 Hz, 2H), 7.47 (t, J=7.7 Hz, 2H),

[0261] 8.11 (d, J=7.7 Hz, 2H).

[Example 22] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of N-vinylphthalimide using Co.SUB.2.(CN.SUP.t.Bu).SUB.8 .as catalyst

[0262] Co.sub.2(CN.sup.tBu).sub.8 obtained in Synthesis Example 1 (3.4 mg, 0.005 mmol), DME (100 μL) as a solvent, N-vinylphthalimide (173 mg, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 1.03 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 6.

[0263] .sup.1H-NMR (400 MHz, CDCl.sub.3) δ:

[0264] 0.07 (s, 9H), 0.14 (s, 6H), 1.03 (m, 2H), 3.75 (m, 2H), 7.69-7.80 (m, 4H).

[Example 23] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of N-vinyl-2-pyrrolidone using Co.SUB.2.(CNAd).SUB.8 .as catalyst

[0265] Co.sub.2(CNAd).sub.8 obtained in Synthesis Example 2 (6.4 mg, 0.005 mmol), N-vinyl-2-pyrrolidone (111 mg, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.81 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 6.

[0266] .sup.1H-NMR (400 MHz, CDCl.sub.3) δ:

[0267] 0.08 (s, 9H), 0.10 (s, 6H), 0.82 (m, 2H), 2.00 (quint, J=7.2, 2H),

[0268] 2.36 (t, J=7.7, 2H), 3.36 (m, 4H).

Comparative Example 4

Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of N-vinyl-2-pyrrolidone using Co.SUB.2.(CO).SUB.8 .as catalyst

[0269] Co.sub.2(CO).sub.8 (1.7 mg, 0.005 mmol), N-vinyl-2-pyrrolidone (111 mg, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.81 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 6.

TABLE-US-00008 TABLE 6 Nitrogen-containing Conversion Yield alkene Product Catalyst (%) (%) Example 19 [00016] [00017] Co.sub.2(CNAd).sub.8 > 99 41 Example 20 [00018] [00019] Co.sub.2(CNAd).sub.8 > 99 73 Example 21 [00020] [00021] Co.sub.2(CNMes).sub.8 > 99 90 Example 22 [00022] [00023] Co.sub.2(CN.sup.tBu).sub.8  60 52 Example 23 [00024] [00025] Co.sub.2(CNAd).sub.8 > 99 82 Comparative Example 4 [00026] [00027] Co.sub.2(CO).sub.8  < 1 < 1

[4] Hydrosilane Reduction Reaction Using, as Substrate, Compound Having Carbon-Oxygen Unsaturated Bond or Carbon-Nitrogen Unsaturated Bond

[Example 24] Hydrosilane reduction reaction by dimethylphenylsilane of acetophenone using Co.SUB.2.(CN.SUP.t.Bu).SUB.8 .as catalyst

[0270] ##STR00028##

[0271] Co.sub.2(CN.sup.tBu).sub.8 obtained in Synthesis Example 1 (3.4 mg, 0.005 mmol), acetophenone (120 mg, 1.0 mmol), and dimethylphenylsilane (177 mg, 1.3 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. The results are shown in Table 7.

[0272] .sup.1H-NMR (400 MHz, CDCl.sub.3):

[0273] 0.28 (s, 3H), 0.33 (s, 3H), 1.42 (d, J=6.4 Hz), 4.85 (q, 6.4 Hz, 1H),

[0274] 7.16-7.41 (m, 8H), 7.53-7.59 (m, 2H).

[Example 25] Hydrosilane reduction reaction by 1,1,3,3-tetramethyldisiloxane of acetophenone using Fe(CN.SUP.t.Bu).SUB.5 .as catalyst

[0275] ##STR00029##

[0276] Fe(CN.sup.tBu).sub.5 obtained in Synthesis Example 4 (4.7 mg, 0.01 mmol), acetophenone (120 mg, 1.0 mmol), and 1,1,3,3-tetramethyldisiloxane (147 mg, 1.3 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. The results are shown in Table 7.

[0277] 1:1 adduct (a); .sup.1H-NMR (400 MHz, CDCl.sub.3):

[0278] 0.02 (s, 3H), 0.10 (s, 3H), 0.13 (d, J=3.0, 3H), 0.14 (d, J=3.0, 3H),

[0279] 1.46 (d, J=6.5 Hz, 3H), 4.66 (m, 1H), 4.98 (q, 6.4 Hz, 1H),

[0280] 7.19-7.37 (m, 5H).

[0281] 1:2 adduct (b); .sup.1H-NMR (400 MHz, CDCl.sub.3):

[0282] 0.05-0.17 (m, 12H), 1.44 (d, J=6.5 Hz, 6H), 4.94 (q, 6.4 Hz, 2H),

[0283] 7.19-7.37 (m, 10H).

Comparative Example 5

Hydrosilane reduction reaction by 1,1,3,3-tetramethyldisiloxane of acetophenone using Fe.SUB.2.(CO).SUB.9 .as catalyst

[0284] Fe.sub.2(CO).sub.5 (1.8 mg, 0.005 mmol), acetophenone (120 mg, 1.0 mmol), and 1,1,3,3-tetramethyldisiloxane (147 mg, 1.3 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. The results are shown in Table 7.

TABLE-US-00009 TABLE 7 Yield Hydrosilane Structure of product Catalyst (%) Example 24 dimethylphenylsilane [00030] Co.sub.2(CNAd).sub.8 > 99 Example 25 1,1,3,3- tetramethyldisiloxane [00031] Fe(CN.sup.tBu).sub.5  52 (a:b = l:l) Comparative Example 5 1,1,3,3- tetramethyldisiloxane [00032] Fe.sub.2(CO).sub.9   8 (a:b = 3:l)

[Example 26] Hydrosilane reduction reaction by diphenylsilane of N,N-dimethylbenzamide using Co.SUB.2.(CNMes).SUB.8 .as catalyst

[0285] ##STR00033##

[0286] Co.sub.2(CNMes).sub.8 obtained in Synthesis Example 3 (6.4 mg, 0.005 mmol), N,N-dimethylbenzamide (149 mg, 1.0 mmol), and diphenylsilane (239 mg, 1.3 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. The results are shown in Table 8.

[0287] .sup.1H-NMR (400 MHz, CDCl.sub.3): 2.24 (s, 6H), 3.42 (s, 2H), 7.30-7.38 (m, 5H).

[Example 27] Hydrosilane reduction reaction by 1,1,3,3-tetramethyldisiloxane of N,N-dimethylbenzamide using Fe(CN.SUP.I.Bu).SUB.5 .as catalyst

[0288] ##STR00034##

[0289] Fe(CN.sup.tBu).sub.5 obtained in Synthesis Example 4 (4.7 mg, 0.01 mmol), N,N-dimethylbenzamide (149 mg, 1.0 mmol), and 1,1,3,3-tetramethyldisiloxane (147 mg, 1.3 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. The results are shown in Table 8.

Comparative Example 6

Hydrosilane reduction reaction by diphenylsilane of N,N-dimethylbenzamide using Co.SUB.2.(CO).SUB.8 .as catalyst

[0290] Co.sub.2(CO).sub.8 (1.7 mg, 0.005 mmol), N,N-dimethylbenzamide (149 mg, 1.0 mmol), and diphenylsilane (239 mg, 1.3 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. The results are shown in Table 8.

TABLE-US-00010 TABLE 8 Yield Hydrosilane Catalyst (%) Example 26 diphenylsilane Co.sub.2(CNMes).sub.8 98 Example 27 1,1,3,3-tetramethyldisiloxane Fe(CN.sup.tBu).sub.5 38 Comparative diphenylsilane Co.sub.2(CO).sub.8  2 Example 6

[Example 28] Hydrosilane reduction reaction by 1,1,3,3-tetramethyldisiloxane of acetonitrile using Co.SUB.2.(CN.SUP.t.Bu).SUB.8 .as catalyst

[0291] ##STR00035##

[0292] Co.sub.2(CN.sup.tBu).sub.8 obtained in Synthesis Example 1 (3.4 mg, 0.005 mmol), acetonitrile (41 mg, 1.0 mmol), and 1,1,3,3-tetramethyldisiloxane (147 mg, 1.3 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, a .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. The results are shown in Table 9.

[0293] .sup.1H-NMR (400 MHz, CDCl.sub.3): [0294] 0.18 (s, 6H), 0.19 (s, 6H), 1.02 (t, J=6.4, 3H), 2.88 (q, J=6.4, 2H).

Comparative Example 7

Hydrosilane reduction reaction by 1,1,3,3-tetramethyldisiloxane of acetonitrile using Co.SUB.2.(CO).SUB.8 .as catalyst

[0295] Co.sub.2(CO).sub.8 (1.7 mg, 0.005 mmol), acetonitrile (41 mg, 1.0 mmol), and 1,1,3,3-tetramethyldisiloxane (147 mg, 1.3 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. The results are shown in Table 9.

TABLE-US-00011 TABLE 9 Yield Product Catalyst (%) Example 28 [00036] Co.sub.2(CN.sup.tBu).sub.8  98 Comparative Example 7 [00037] Co.sub.2(CO).sub.8 < 1

[5] Hydrogenation Reaction Using Compound Having Carbon-Carbon Unsaturated Bond as Substrate

[Example 29] Hydrogenation Reaction of 1-octene Using Co.SUB.2.(CN.SUP.t.Bu).SUB.8 .as catalyst

[0296] Co.sub.2(CN.sup.tBu).sub.8 obtained in Synthesis Example 1 (6.4 mg, 0.005 mmol) and 1-octene (1.12 g, 10 mmol) were added to a reactor for an autoclave, hydrogen at 10 atm. was introduced, and stirring was performed at 80° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. The results are shown in Table 10.

[0297] .sup.1H-NMR (CDCl.sub.3, 400 MHz): δ=0.88 (t, J=7.2 Hz, 6H), 1.16-1.36 (m, 12H).

[Example 30] Hydrogenation Reaction of Styrene Using Fe(CN.SUP.t.Bu).SUB.5 .as catalyst

[0298] Fe(CN.sup.tBu).sub.5 obtained in Synthesis Example 4 (4.7 mg, 0.01 mmol) and styrene (1.04 g, 10 mmol) were added to a reactor for an autoclave, hydrogen at 10 atm. was introduced, and stirring was performed at 80° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. The results are shown in Table 10.

[0299] .sup.1H-NMR (CDCl.sub.3, 400 MHz):

δ=1.13 (t, J=7.2 Hz, 3H), 2.54 (q, J=7.2 Hz, 2H), 7.02-7.20 (m, 5H)

[0300]

TABLE-US-00012 TABLE 10 Yield Alkene Catalyst Product (%) TON Example 29 1-octene Co.sub.2(CN.sup.tBu).sub.8 octane >99 1,000 Example 30 styrene Fe(CN.sup.tBu).sub.5 ethyl benzene   22   220

[Example 31] Hydrosilylation reaction by triethylsilane of α-methylstyrene using Co.SUB.2.(CN.SUP.t.Bu).SUB.8 .as catalyst

[0301] Co.sub.2(CN.sup.tBu).sub.8 obtained in Synthesis Example 1 (3.4 mg, 0.005 mmol), α-methylstyrene (129 μL, 1.0 mmol), and triethylsilane (151 mg, 1.3 mmol) were added to a reactor, and stirring was performed at 25° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet of 2.86 ppm in the desired product was observed, and the yield was found. The results are shown in Table 11.

[0302] .sup.1H-NMR (396 MHz, CDCl.sub.3) δ:

7.21-7.27 (m, 4H), 7.15-7.17 (m, 1H), 2.86 (sext, J=6.8, 1H)

1.27 (d, J=6.8, 3H), 0.98 (dd, J=14.8, 6.8 Hz, 1H)

0.90 (dd, J=14.8, 6.8 Hz, 1H), 0.86 (t, J=8.0, 9H), 0.34-0.48 (m, 6H)

[Example 32] Hydrosilylation reaction by dimethylphenylsilane of α-methylstyrene using Co.SUB.2.(CN.SUP.t.Bu).SUB.8 .as catalyst

[0303] Co.sub.2(CN.sup.tBu).sub.8 obtained in Synthesis Example 1 (3.4 mg, 0.005 mmol), α-methylstyrene (129 μL, 1.0 mmol), and dimethylphenylsilane (177 mg, 1.3 mmol) were added to a reactor, and stirring was performed at 25° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet of 2.85 ppm in the desired product was observed, and the yield was found. The results are shown in Table 11.

[0304] .sup.1H-NMR (396 MHz, CDCl.sub.3) δ:

7.44-7.47 (2H, m), 7.31-7.34 (3H, m), 7.21-7.26 (2H, m)

7.11-7.17 (3H, m), 2.85 (sext, J=6.8, 1H), 1.23 (d, J=6.8, 3H)

1.22 (dd, J=14.8, 6.8 Hz, 1H), 1.15 (dd, J=14.8, 6.8 Hz, 1H)

0.15 (s, 3H), 0.09 (s, 3H)

[0305]

TABLE-US-00013 TABLE 11 Conversion Yield Silane Catalyst (%) (%) Example 31 triethylsilane Co.sub.2(CN.sup.tBu).sub.8 >99 >99 Example 32 dimethylphenylsilane Co.sub.2(CN.sup.tBu).sub.8 >99 >99

[Example 33] Hydrosilylation reaction by polydimethylsiloxane endblocked at both terminals by dimethylhydrogensiloxy groups of α-methylstyrene using Co.SUB.2.(CNAd).SUB.8 .as catalyst

[0306] Co.sub.2(CNAd).sub.8 obtained in Synthesis Example 2 (6.4 mg, 0.005 mmol), α-methylstyrene (1.53 mg, 13 mmol), and polydimethylsiloxane endblocked at both terminals by dimethylhydrogensiloxy groups (degree of polymerization 18) (7.4 g, 5.0 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.98 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found (yield >99%).

[0307] .sup.1H-NMR (396 MHz, CDCl.sub.3) δ:

7.27 (t, J=6.8, 2H), 7.21 (d, J=6.8, 2H), 7.15 (t, J=6.8, 1H)

2.92 (sext, J=6.8, 1H), 1.28 (d, J=6.8, 3H), 0.90-0.98 (m, 2H)

0.05 (s), −0.05 (s), −0.07 (s)

[Example 34] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of α-methylstyrene using, as a catalyst, substance obtained by allowing Co.SUB.2.(CNMes).SUB.8 .to stand in air for 24 hours

[0308] Co.sub.2(CNMes).sub.8 obtained in Synthesis Example 3 (6.4 mg, 0.005 mmol) was added to a reactor in a glove box. The reactor was taken out of the glove box, and was allowed to stand in air at room temperature for 24 hours. After that, the reactor was brought into the glove box, α-methylstyrene (129 μL, 1.0 mmol) and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to the reactor, and stirring was performed at 25° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.94 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found (yield >99%).

[Example 35] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of styrene using Fe(CNAd).SUB.5 .as catalyst

[0309] Fe(CNAd).sub.5 obtained in Synthesis Example 5 (8.6 mg, 0.01 mmol), styrene (114 μL, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.90 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 12.

[Example 36] Hydrosilylation reaction by diethoxy(methyl)silane of styrene using Fe(CNAd).SUB.5 .as catalyst

[0310] Fe(CNAd).sub.5 obtained in Synthesis Example 5 (8.6 mg, 0.01 mmol), styrene (114 μL, 1.0 mmol), and diethoxy(methyl)silane (175 mg, 1.3 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.90 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 12.

[0311] .sup.1H-NMR (396 MHz, CDCl.sub.3) δ:

7.20 (m, 5H), 3.80 (m, 4H) 2.68-2.72 (m, 2H), 1.23 (t, J=6.8, 6H)

0.97-1.01 (m, 2H), 0.12 (s, 3H)

[0312]

TABLE-US-00014 TABLE 12 Conversion Yield Silane Catalyst (%) (%) Example 35 1,1,1,3,3- Fe(CNAd).sub.5 >99 >99 pentamethyldisiloxane Example 36 diethoxy(methyl)silane Fe(CNAd).sub.5 >99 >99

[Example 37] Hydrosilylation reaction by polydimethylsiloxane endblocked at both terminals by dimethylhydrogensiloxy groups of styrene using Fe(CNAd).SUB.5 .as catalyst

[0313] Fe(CNAd).sub.5 obtained in Synthesis Example 5 (8.6 mg, 0.01 mmol), styrene (154 μL, 1.3 mmol), and polydimethylsiloxane endblocked at both terminals by dimethylhydrogensiloxy groups (degree of polymerization 18) (0.74 g, 0.50 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.90 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 13.

[0314] .sup.1H-NMR (396 MHz, CDCl.sub.3) δ:

7.24-7.29 (m, 2H), 7.13-7.22 (m, 3H), 2.61-2.68 (m, 2H)

0.86-0.92 (m, 2H), 0.08 (s), 0.07 (s)

[0315]

TABLE-US-00015 TABLE 13 Conversion of Si-H Yield (%) (%) Example 37 >99 >99

[Example 38] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of styrene using Ni(CN.SUP.t.Bu).SUB.4 .as catalyst

[0316] ##STR00038##

[0317] Ni(CN.sup.tBu).sub.4 obtained in Synthesis Example 6 (3.9 mg, 0.01 mmol), styrene (114 μL, 0.01 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 80° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 2.65 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found (yield: 39%).

[0318] .sup.1H-NMR (396 MHz, CDCl.sub.3) δ:

7.22-7.29 (m, 5H), 2.65 (q, J=7.6 Hz, 1H), 1.35 (d, J=7.6 Hz, 2H)

0.01 (s, 9H), −0.01 (s, 3H), −0.02 (s, 3H)

[Example 39] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of 1,1,1,3,3-pentamethyl-3-vinyldisiloxane using Co.SUB.2.(CNMes).SUB.8 .as catalyst

[0319] Co.sub.2(CNMes).sub.8 obtained in Synthesis Example 3 (6.4 mg, 0.005 mmol), 1,1,1,3,3-pentamethyl-3-vinyldisiloxane (174 mg, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 80° C. for 3 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.40 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 14.

[0320] .sup.1H-NMR (396 MHz, CDCl.sub.3) δ: 0.03 (s, 12H), 0.06 (s, 18H), 0.40 (s, 4H).

[Example 40] Hydrosilylation reaction by 1,1,1,3,3-pentamethyldisiloxane of vinyltriethoxysilane using Co.SUB.2.(CN.SUP.t.Bu).SUB.8 .as catalyst

[0321] Co.sub.2(CN.sup.tBu).sub.8 obtained in Synthesis Example 1 (3.4 mg, 0.005 mmol), vinyltriethoxysilane (190 mg, 1.0 mmol), and 1,1,1,3,3-pentamethyldisiloxane (254 μL, 1.3 mmol) were added to a reactor, and stirring was performed at 50° C. for 24 hours. After the reaction ended, .sup.1H-NMR spectrum was measured to determine the structure and the yield of the product. A multiplet at 0.50 ppm, which is a signal of protons on carbon adjacent to silicon in the desired product, was observed, and the yield was found. The results are shown in Table 14.

[0322] .sup.1H-NMR (396 MHz, CDCl.sub.3) δ:

3.78 (6H, q, J=7.0 Hz), 1.19 (9H, t, J=7.0 Hz), 0.47-0.53 (4H, m)

0.02 (9H, s), 0.00 (6H, s)

[0323]

TABLE-US-00016 TABLE 14 Conversion Yield Alkene Catalyst (%) (%) Example 39 1,1,1,3,3- Co.sub.2(CNMes).sub.8   83 30 pentamethyl-3- vinyldisiloxane Example 40 vinyltriethoxysilane Co.sub.2(CN.sup.tBu).sub.8 >99 53