Various embodiments disclosed relate to bridged phthalocyanine- and napththalocyanine-metal complex catalysts and methods using the same for oxidation reactions. In various embodiments, the present invention provides a method of oxidation including contacting an oxidizable starting material including an alkene with a catalyst and an oxidant, to provide an oxidized product.

Various embodiments disclosed relate to bridged phthalocyanine- and napththalocyanine-metal complex catalysts and methods using the same for oxidation reactions. In various embodiments, the present invention provides a method of oxidation including contacting an oxidizable starting material including an alkene with a catalyst and an oxidant, to provide an oxidized product.

A method for producing a carbonyl compound represented by formula (1): ##STR00001##
wherein R.sup.1 is hydrogen or an organic group; R.sup.2 is hydrogen or an organic group; and R.sup.3 is hydrogen or an organic group; or two or three of R.sup.1, R.sup.2, and R.sup.3 may be linked to form a ring that may have at least one substituent, the method comprising step A of oxidizing an olefin compound represented by formula (2): ##STR00002##
wherein symbols are as defined above, by an oxidizing agent in the presence of (a) a non-alcohol organic solvent, (b) water, (c) a metal catalyst, and (d) an additive represented by the formula: MXn, wherein M is an element belonging to any one of Group 1, Group 2, Group 13, Group 14, and Group 15 in the periodic table, or NR.sub.4, wherein R is hydrogen or a C.sub.1-10 organic group; X is halogen; and n is a number of 1 to 5.

A method for producing a carbonyl compound represented by formula (1): ##STR00001##
wherein R.sup.1 is hydrogen or an organic group; R.sup.2 is hydrogen or an organic group; and R.sup.3 is hydrogen or an organic group; or two or three of R.sup.1, R.sup.2, and R.sup.3 may be linked to form a ring that may have at least one substituent, the method comprising step A of oxidizing an olefin compound represented by formula (2): ##STR00002##
wherein symbols are as defined above, by an oxidizing agent in the presence of (a) a non-alcohol organic solvent, (b) water, (c) a metal catalyst, and (d) an additive represented by the formula: MXn, wherein M is an element belonging to any one of Group 1, Group 2, Group 13, Group 14, and Group 15 in the periodic table, or NR.sub.4, wherein R is hydrogen or a C.sub.1-10 organic group; X is halogen; and n is a number of 1 to 5.

A method for producing a carbonyl compound represented by formula (1): ##STR00001##
wherein R.sup.1 is hydrogen or an organic group; R.sup.2 is hydrogen or an organic group; and R.sup.3 is hydrogen or an organic group; or two or three of R.sup.1, R.sup.2, and R.sup.3 may be linked to form a ring that may have at least one substituent, the method comprising step A of oxidizing an olefin compound represented by formula (2): ##STR00002##
wherein symbols are as defined above, by an oxidizing agent in the presence of (a) a non-alcohol organic solvent, (b) water, (c) a metal catalyst, and (d) an additive represented by the formula: MXn, wherein M is an element belonging to any one of Group 1, Group 2, Group 13, Group 14, and Group 15 in the periodic table, or NR.sub.4, wherein R is hydrogen or a C.sub.1-10 organic group; X is halogen; and n is a number of 1 to 5.

A process is proposed for preparing unsaturated macrocyclic monoketones, comprising the following steps: (a) providing macrocyclic dienes having a ring size of at least 9 carbon atoms; (b) contacting the starting materials from step (a) with (b1) a palladium(II) salt and/or a palladium(II) complex; and (b2) an oxidizing agent; and (b3) a solvent; and optionally (b4) a ligand; and optionally (b5) a co-catalyst; and optionally (b6) an acid,
with the proviso that the co-catalyst (b5) comprises or consists of a divalent or trivalent iron salt which is different from FeSO.sub.4 and is preferably iron(III) nitrate.

A process is proposed for preparing unsaturated macrocyclic monoketones, comprising the following steps: (a) providing macrocyclic dienes having a ring size of at least 9 carbon atoms; (b) contacting the starting materials from step (a) with (b1) a palladium(II) salt and/or a palladium(II) complex; and (b2) an oxidizing agent; and (b3) a solvent; and optionally (b4) a ligand; and optionally (b5) a co-catalyst; and optionally (b6) an acid,
with the proviso that the co-catalyst (b5) comprises or consists of a divalent or trivalent iron salt which is different from FeSO.sub.4 and is preferably iron(III) nitrate.

A process is proposed for preparing unsaturated macrocyclic monoketones, comprising the following steps: (a) providing macrocyclic dienes having a ring size of at least 9 carbon atoms; (b) contacting the starting materials from step (a) with (b1) a palladium(II) salt and/or a palladium(II) complex; and (b2) an oxidizing agent; and (b3) a solvent; and optionally (b4) a ligand; and optionally (b5) a co-catalyst; and optionally (b6) an acid,
with the proviso that the co-catalyst (b5) comprises or consists of a divalent or trivalent iron salt which is different from FeSO.sub.4 and is preferably iron(III) nitrate.

A long life catalyst is provided that is conveniently and inexpensively capable of being produced and that is highly active and has inhibited metal leakage. According to aspects of the present invention, a catalyst is provided that includes: a polymer including a plurality of first structural units and a plurality of second structural units; and metal acting as a catalytic center, wherein at least part of the metal is covered with the polymer, each of the plurality of first structural units has a first atom constituting a main chain of the polymer and a first substituent group bonded to the first atom, a second atom included in each of the plurality of second structural units is bonded to the first atom, and the second atom is different from the first atom, or at least one of all substituent groups on the second atom is different from the first substituent group.

A long life catalyst is provided that is conveniently and inexpensively capable of being produced and that is highly active and has inhibited metal leakage. According to aspects of the present invention, a catalyst is provided that includes: a polymer including a plurality of first structural units and a plurality of second structural units; and metal acting as a catalytic center, wherein at least part of the metal is covered with the polymer, each of the plurality of first structural units has a first atom constituting a main chain of the polymer and a first substituent group bonded to the first atom, a second atom included in each of the plurality of second structural units is bonded to the first atom, and the second atom is different from the first atom, or at least one of all substituent groups on the second atom is different from the first substituent group.