Patent ID: 7238832

Claim:
A method for producing a coupling compound of formula (1): (Y—) (n−1) R 1 —R 2 —(R 1 ) (n′−1) (1) wherein R 1 , R 2 n and n′ are as defined below, Y is R 2 X as defined below, which method comprises reacting an organic halogen compound of formula (2): n′(R 1 X 1 n ) (2) wherein X 1 represents a bromine or iodine, R 1 represents a substituted or unsubstituted, linear, branched or cyclic hydrocarbon group of which α and β carbon atoms in relation to X 1 are sp3 carbon atoms, n and n′ each independently represent an integer of 1 or 2, and provided that n and n′ do not simultaneously represent 2, with an organic boron compound of formula (3): m{R 2 (BX 2 2 ) n′ } (3) wherein R 2 represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkenyl group and the boron atom is bonded with a sp2 carbon atom thereof, X 2 represents a hydroxyl or alkoxy group, n′ is as defined above, m represents an integer of 1 or 2, and m is not more than n, in the presence of a catalyst comprising a) a nickel compound, and b) b-1) a compound of formula (i): wherein R 3 and R 4 each independently represent an alkyl, aryl, alkenyl, alkynyl, alkoxyl, hydroxy, hydroxyalkyl, sulfo, alkyloxycarbonyl, aryloxycarbonyl, carbamoyl, cyano, isocyano, cyanato, isocyanato or formyl group, or a hydrocarbylsilyl group, and optionally two adjacent groups among R 3 and R 4 groups with the carbon atoms to which they are bonded form a ring, a and b are the same or different and independently represent an integer of 0 to 4, or b-2) a compound of formula (ii): wherein R 5 , R 6 and R 7 groups are the same or different and independently represent an alkyl, aryl, alkenyl, alkynyl, alkoxyl, hydroxy, sulfo, alkyloxycarbonyl, aryloxycarbonyl, carbamoyl, cyano, isocyano, cyanato, isocyanato or formyl group, or a hydrocarbylsilyl group, and optionally two adjacent groups among R 5 , R 6 , and R 7 groups with the carbon atoms to which they are bonded form a ring, c, and e are the same or different and independently represent an integer of 0 to 3, and d represents an integer of 0 to 2; or a mixture thereof.