Patent ID: 8237002

Claim:
A method for producing an unsaturated organic compound represented by the formula (3): (Y 1 ) m-1 —R 1 —R 2 —(Y 2 ) n-1 (3) wherein R 1 represents a substituted or unsubstituted m-valent aromatic group, a substituted or unsubstituted m-valent heteroaromatic group, or a substituted or unsubstituted m-valent aliphatic hydrocarbon group having at least one double bond, R 2 represents a substituted or unsubstituted n-valent aromatic group, a substituted or unsubstituted n-valent heteroaromatic group, or a substituted or unsubstituted n-valent aliphatic hydrocarbon group having at least one double bond, m represents 1 or 2, n represents 1 or 2, with the proviso that when m is 2, n is 1, Y 1 represents R 2 or X 1 , Y 2 represents R 1 or B(X 2 ) 2 , X 1 independently represents a leaving group bonded to a sp 2 carbon, X 2 independently represents a hydroxyl group or an alkoxy group, or two X 2 are bonded to a ring containing a boron atom, and a group represented by —B(X 2 ) 2 are bonded to a sp 2 carbon, which comprises reacting a compound represented by the formula (1): R 1 (X 1 ) m (1) wherein R 1 , X 1 and m are the same as defined above, with a compound represented by the formula (2): R 2 {B(X 2 ) 2 } n (2) wherein R 2 , X 2 and n are the same as defined above, in the presence of (a) at least one nickel compound selected from the group consisting of a nickel carboxylate, nickel nitrate and a nickel halide, (b) a phosphine compound represented by the formula (A): wherein R 3 is independently in each occurrence a C3-C7 alkyl group or a C3-C7 cycloalkyl group, and p represents 2, 3 or 4, (c) at least one amine selected from the group consisting of a primary amine and an amine represented by the formula (B): wherein R 4 is independently in each occurrence a substituted or unsubstituted C1-C10 alkyl group, and r represents an integer of 1 to 6, and (d) an inorganic base.