Production method of a coupling compound

Abstract

There is provided a method for producing a coupling compound of formula (1):(Y—)R—R—(R)  (1)wherein R, Rn and n' are as defined below, Y is Ror X as defined below, which method comprises reacting an organic halogen compound of formula (2):n′(RX)  (2)wherein Xrepresents a bromine or iodine, Rrepresents a substituted or unsubstituted, linear, branched or cyclic hydrocarbon group of which α and β carbon atoms in relation to Xare 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(BX)}  (3)wherein Rrepresents a substituted or unsubstituted aryl group or a substituted or unsubstituted alkenyl group and the boron atom is bonded with a sp2 carbon atom thereof, Xrepresents 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 or