Production method of a coupling compound

A method for producing a coupling compound of formula (1):

• (Y—)(n−1)R1—R2—(R1)(n′−1) (1)
• wherein R1, R2 n and n′ are as defined below,
• Y is R2 or X as defined below,
• which method comprises reacting
• an organic halogen compound of formula (2):
• n′(R1X1n) (2)
• wherein X1 represents a bromine or iodine,
• R1 represents a substituted or unsubstituted, linear, branched or cyclic hydrocarbon group of which α and β carbon atoms in relation to X1 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{R2(BX22)n′} (3)
• wherein R2 represents 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,
• X2 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):
• 80
• wherein R3 and R4 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 R3 and R4 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):
• 81
• wherein R5, R6 and R7 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 R5, R6, and R7 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.