Heterogeneous rhodium metal catalysts

A compound of formula II:

• wherein
• R1, R2, R3 and R4 are independently selected from phenyl and C4-8cycloalkyl, the latter two groups being unsubstituted or substituted, where possible, with 1, 2, 3, 4, or 5 groups independently selected from C1-6alkyl, OC1-6alkyl and halo;
• is a binaphthyl group or a derivative of a binaphthyl group, each being unsubstituted or substituted with one or more groups independently selected from C1-6alkyl, OC1-6alkyl and halo;
• X is an anionic ligand;
• and
• is a monocyclic, bicyclic or tricylic group comprising at least one double bond and being unsubstituted or substituted with one or more groups independently selected from C1-6alkyl, OC1-6alkyl, halo and ═O.

A method of performing metal-catalyzed organic synthesis reactions comprising contacting substrates for the organic synthesis reaction with a catalyst comprising repeating subunits of the formula I, a catalyst comprising a compound of formula II, or a combination thereof, under conditions for performing the organic synthesis reaction, and optionally isolating one or more products from the organic synthesis reaction;

• wherein
• R1, R2, R3 and R4 are independently selected from phenyl and C4-8cycloalkyl, the latter two groups being unsubstituted or substituted, where possible, with 1, 2, 3, 4, or 5 groups independently selected from C1-6alkyl, OC1-6alkyl and halo;
• is a binaphthyl group or a derivative of a binaphthyl group, each being unsubstituted or substituted with one or more groups independently selected from C1-6alkyl, OC1-6alkyl and halo;
• is a monocyclic, bicyclic or tricylic group comprising at least one double bond and being unsubstituted or substituted with one or more groups independently selected from C1-6alkyl, OC1-6alkyl, halo and ═O;
• R5, R6, R7 and R8 are independently selected from H, C1-6alkyl, OC1-6alkyl and halo;
• or
• R5 and R6 and/or R7 and R8 are ═O;
• or
• one of R5 and R6 is linked to one of R7 and R8 to form, together with the atoms to which they are attached and the atoms connecting them, a monocyclic, bicyclic or tricylic ring system;
• R5, R6, R7 and R8 in each methylene unit is the same or different, and means the double bond attached to this bond is in the cis or trans configuration, if applicable;
• m and n are, independently, an integer between and including 0 and 10;
• p is an integer between and including 1 and 14;
• and
• X is an anionic ligand.

A method for the intramolecular cycloisomerization of enynes comprising contacting one or more compounds having at least one enyne grouping with a catalyst comprising repeating subunits of the formula I, a catalyst comprising a compound of formula II, or a combination thereof, in the presence of an anion abstracting agent under conditions suitable for the intramolecular cycloisomerization of the at least one enyne grouping;

• wherein
• R1, R2, R3 and R4 are independently selected from phenyl and C4-8cycloalkyl, the latter two groups being unsubstituted or substituted, where possible, with 1, 2, 3, 4, or 5 groups independently selected from C1-6alkyl, OC1-6alkyl and halo;
• is a binaphthyl group or a derivative of a binaphthyl group, each being unsubstituted or substituted with one or more groups independently selected from C1-6alkyl, OC1-6alkyl and halo;
• is a monocyclic, bicyclic or tricylic group comprising at least one double bond and being unsubstituted or substituted with one or more groups independently selected from C1-6alkyl, OC1-6alkyl, halo and ═O;
• R5, R6, R7 and R8 are independently selected from H, C1-6alkyl, OC1-6alkyl and halo;
• or
• R5 and R6 and/or R7 and R8 are ═O;
• or
• one of R5 and R6 is linked to one of R7 and R8 to form, together with the atoms to which they are attached and the atoms connecting them, a monocyclic, bicyclic or tricylic ring system;
• R5, R6, R7 and R8 in each methylene unit is the same or different, and means the double bond attached to this bond is in the cis or trans configuration, if applicable;
• m and n are, independently, an integer between and including 0 and 10;
• p is an integer between and including 1 and 14;
• and
• X is an anionic ligand.

A composition comprising a compound of formula I, a compound of formula II, or a mixture thereof and an anion abstracting agent;

• wherein
• R1, R2, R3 and R4 are independently selected from phenyl and C4-8cycloalkyl, the latter two groups being unsubstituted or substituted, where possible, with 1, 2, 3, 4, or 5 groups independently selected from C1-6alkyl, OC1-6alkyl and halo;
• is a binaphthyl group or a derivative of a binaphthyl group, each being unsubstituted or substituted with one or more groups independently selected from C1-6alkyl, OC1-6alkyl and halo;
• is a monocyclic, bicyclic or tricylic group comprising at least one double bond and being unsubstituted or substituted with one or more groups independently selected from C1-6alkyl, OC1-6alkyl, halo and ═O;
• R5, R6, R7 and R8 are independently selected from H, C1-6alkyl, OC1-6alkyl and halo;
• or R5 and R6 and/or R7 and R8 are ═O;
• or
• one of R5 and R6 is linked to one of R7 and R8 to form, together with the atoms to which they are attached and the atoms connecting them, a monocyclic, bicyclic or tricylic ring system;
• R5, R6, R7 and R8 in each methylene unit is the same or different, and means the double bond attached to this bond is in the cis or trans configuration, if applicable;
• m and n are, independently, an integer between and including 0 and 10;
• p is an integer between and including 1 and 14;
• and
• X is an anionic ligand.

A kit comprising a compound of formula I, a compound of formula II, or a mixture thereof and an anion abstracting agent, either in one composition or in separate compositions, optionally, with instructions for use;

• wherein
• R1, R2, R3 and R4 are independently selected from phenyl and C4-8cycloalkyl, the latter two groups being unsubstituted or substituted, where possible, with 1, 2, 3, 4, or 5 groups independently selected from C1-6alkyl, OC1-6alkyl and halo;
• is a binaphthyl group or a derivative of a binaphthyl group, each being unsubstituted or substituted with one or more groups independently selected from C1-6alkyl, OC1-6alkyl and halo;
• is a monocyclic, bicyclic or tricylic group comprising at least one double bond and being unsubstituted or substituted with one or more groups independently selected from C1-6alkyl, OC1-6alkyl, halo and ═O;
• R5, R6, R7 and R8 are independently selected from H, C1-6alkyl, OC1-6alkyl and halo;
• or
• R5 and R6 and/or R7 and R8 are ═O;
• or
• one of R5 and R6 is linked to one of R7 and R8 to form, together with the atoms to which they are attached and the atoms connecting them, a monocyclic, bicyclic or tricylic ring system;
• R5, R6, R7 and R8 in each methylene unit is the same or different, and means the double bond attached to this bond is in the cis or trans configuration, if applicable;
• m and n are, independently, an integer between and including 0 and 10;
• p is an integer between and including 1 and 14;
• and
• X is an anionic ligand.