Patent ID: 7041856

Claim:
A process for producing a coupling compound of formula (1): (Y—) (n−1) R 1 —R 2 —(R 1 ) (n′−1) (1), wherein R 1 and R 2 independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted linear, branched or cyclic alkenyl group, n and n′ independently represent an integer of 1 or 2, provided that n and n′ do not simultaneously represent 2, and when n=2, Y represents R 2 , or X 1 as defined below, which process comprises reacting an unsaturated organic compound of formula (2): n ′(R 1 X 1 n ) (2) wherein n, n′, and R 1 are the same as defined above, and X 1 is the same or different and independently represents a leaving group and is bonded with a sp2 carbon atom of R 1 group, with a boron compound of formula (3); m {R 2 (BX 2 2 ) n′ } (3) wherein R 2 and n′ are the same as defined above, X 2 represents a hydroxy group, an alkoxy group, or X 2 groups are bonded at their terminals to form an alkylenedioxy group or an arylenedioxy group, and m represents an integer of 1 or 2, provided that the boron atom is bonded with a sp2 carbon atom of R 2 group, and m≦n, wherein n is the same as defined in connection with formula (1) above, or a cyclic anhydride trimer thereof of formula: (—O—B (R 2 )—) 3 , wherein R 2 is the same as defined above, in the presence of a catalyst comprising (A) a nickel compound, and (B) a nitrogen-containing cyclic compound selected from the group consisting of: (a) a nitrogen-containing cyclic compound of formula (I): wherein Q represents a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted 1,2-phenylene group, a substituted or unsubstituted 1,8-naphthylene group, or —N═N— group, R 10 represents a substituted or unsubstituted hydrocarbon group, and R 20 represents a hydrogen atom, a substituted or unsubstituted hydrocarbon group, alternatively, R 10 and R 20 are bonded at their terminals to form a substituted or unsubstituted alkylene, or alkenylene group, (b) a substituted or unsubstituted pyridine or fused ring compound thereof of which conjugated acid has pKa of 5 or more, (c) a substituted pyrimidine or substituted or unsubstituted fused pyrimidine compound of which conjugate acid has pKa of 3 or more, (d) an enamine compound obtainable from a cyclic ketone compound and a cyclic secondary amine compound, (e) a substituted or unsubstituted 2H-pyrrole, 3,4-dihydro-2H-pyrrole or 3H-pyrrole or fused ring compound thereof, or (f) a substituted or unsubstituted N-hydrocarbyl 1,2,3-triazole, or a fused ring compound thereof.