The present application discloses a 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-based phosphine ligand, an intermediate, a preparation method and uses thereof. The compound of phosphine ligand is a compound having a structure represented by formula I or formula II, or an enantiomer, a raceme, or diastereomer thereof. The phosphine ligand can be prepared via a preparation scheme in which the cheap and easily available 6,6′-dihydroxyl-3,3,3′,3′-tetramethyl-1,1′-spirobiindane is used as a raw material and the compound represented by formula III serves as the key intermediate. The new phosphine ligand developed by the present application can be used in catalytic organic reaction, in particular as a chiral phosphine ligand that is widely used in many asymmetric catalytic reactions including asymmetric hydrogenation and asymmetric allyl alkylation, and thus it has economic practicability and industrial application prospect. ##STR00001##

The present application discloses a 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-based phosphine ligand, an intermediate, a preparation method and uses thereof. The compound of phosphine ligand is a compound having a structure represented by formula I or formula II, or an enantiomer, a raceme, or diastereomer thereof. The phosphine ligand can be prepared via a preparation scheme in which the cheap and easily available 6,6′-dihydroxyl-3,3,3′,3′-tetramethyl-1,1′-spirobiindane is used as a raw material and the compound represented by formula III serves as the key intermediate. The new phosphine ligand developed by the present application can be used in catalytic organic reaction, in particular as a chiral phosphine ligand that is widely used in many asymmetric catalytic reactions including asymmetric hydrogenation and asymmetric allyl alkylation, and thus it has economic practicability and industrial application prospect. ##STR00001##

The present application discloses a 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-based phosphine ligand, an intermediate, a preparation method and uses thereof. The compound of phosphine ligand is a compound having a structure represented by formula I or formula II, or an enantiomer, a raceme, or diastereomer thereof. The phosphine ligand can be prepared via a preparation scheme in which the cheap and easily available 6,6′-dihydroxyl-3,3,3′,3′-tetramethyl-1,1′-spirobiindane is used as a raw material and the compound represented by formula III serves as the key intermediate. The new phosphine ligand developed by the present application can be used in catalytic organic reaction, in particular as a chiral phosphine ligand that is widely used in many asymmetric catalytic reactions including asymmetric hydrogenation and asymmetric allyl alkylation, and thus it has economic practicability and industrial application prospect.

##STR00001##

The present application discloses a 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-based phosphine ligand, an intermediate, a preparation method and uses thereof. The compound of phosphine ligand is a compound having a structure represented by formula I or formula II, or an enantiomer, a raceme, or diastereomer thereof. The phosphine ligand can be prepared via a preparation scheme in which the cheap and easily available 6,6′-dihydroxyl-3,3,3′,3′-tetramethyl-1,1′-spirobiindane is used as a raw material and the compound represented by formula III serves as the key intermediate. The new phosphine ligand developed by the present application can be used in catalytic organic reaction, in particular as a chiral phosphine ligand that is widely used in many asymmetric catalytic reactions including asymmetric hydrogenation and asymmetric allyl alkylation, and thus it has economic practicability and industrial application prospect.

##STR00001##

A monomer having formula (A) is provided. R.sup.A is H, methyl or trifluoromethyl, X.sup.1 is a single bond, ether, ester or amide bond, R.sup.a is a C.sub.1-C.sub.20 monovalent hydrocarbon group, R.sup.b is H or an acid labile group, X is halogen, n is an integer of 1 to 4, m is an integer of 0 to 3, and 1n+m4. A resist composition comprising a polymer derived from the monomer has a high sensitivity to high-energy radiation, especially EUV. ##STR00001##

A monomer having formula (A) is provided. R.sup.A is H, methyl or trifluoromethyl, X.sup.1 is a single bond, ether, ester or amide bond, R.sup.a is a C.sub.1-C.sub.20 monovalent hydrocarbon group, R.sup.b is H or an acid labile group, X is halogen, n is an integer of 1 to 4, m is an integer of 0 to 3, and 1n+m4. A resist composition comprising a polymer derived from the monomer has a high sensitivity to high-energy radiation, especially EUV. ##STR00001##

A method for synthesizing halogenated organic compounds, such as halogenated alkenyl group-containing and halogenated alkyl group-containing compounds having a heteroatom (e.g., O,N.S) coupled to a carbon atom of a halogenated alkenyl or halogenated alkyl group, involves reacting a halogenated olefin such as a chloro-substituted trifluoropropenyl compound with an active hydrogen-containing organic compound such as an alcohol (e.g., an aliphatic monoalcohol, aliphatic polyalcohol, or a phenolic compound), a primary amine, a secondary amine or a thiol.

A method for synthesizing halogenated organic compounds, such as halogenated alkenyl group-containing and halogenated alkyl group-containing compounds having a heteroatom (e.g., O,N.S) coupled to a carbon atom of a halogenated alkenyl or halogenated alkyl group, involves reacting a halogenated olefin such as a chloro-substituted trifluoropropenyl compound with an active hydrogen-containing organic compound such as an alcohol (e.g., an aliphatic monoalcohol, aliphatic polyalcohol, or a phenolic compound), a primary amine, a secondary amine or a thiol.

A method for synthesizing halogenated organic compounds, such as halogenated alkenyl group-containing and halogenated alkyl group-containing compounds having a heteroatom (e.g., O,N.S) coupled to a carbon atom of a halogenated alkenyl or halogenated alkyl group, involves reacting a halogenated olefin such as a chloro-substituted trifluoropropenyl compound with an active hydrogen-containing organic compound such as an alcohol (e.g., an aliphatic monoalcohol, aliphatic polyalcohol, or a phenolic compound), a primary amine, a secondary amine or a thiol.

Fluorinated cyclopentene moieties and fluorinated cyclopentene functionalized silica materials are provided. The fluorinated cyclopentene functionalized silica materials include a silica material having the fluorinated cyclopentene moiety covalently bonded thereto. Exemplary silica materials include a polysilsesquioxane, a nanosilica, a microsilica, a silica gel, a silica aerogel, or combinations thereof. The fluorinated cyclopentene moieties are based on a modification of perfluorocyclopentene (i.e., 1,2,3,3,4,4,5,5-octafluoro-1-cyclopentene) by nucleophilic substitution with an appropriate nucleophile having a reactive functional group. Methods for preparing fluorinated cyclopentene moieties and the corresponding fluorinated cyclopentene functionalized silica materials are also provided.