Production method of a cross-coupling compound from an alkyl halide and an organoboron compound

摘要

There is provided a method for producing a coupling compound of formula (1): (Y-)(n-1)R<1>-R<2>-(R<1>)(n'-1) wherein R<1>, R<2> n and n' are as defined below, Y is R<2> or X as defined below, which method comprises reactinganorganichalogen compound of formula (2): n' (R<1>X<1>n) wherein X<1> represents a bromine or iodine, R<1> represents a substituted or unsubstituted, linear, branched or cyclic hydrocarbon group of which alpha and beta 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): mäR<2>(BX<2>2)n'ü wherein R<2> represents a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or substituted or unsubstituted alkenyl group and the boron atom is bonded with an 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): or b-2) a compound of formula (ii):