Reaction of α-substituted β-bromostyrenes with dicarbonyldicyanonickelate(0) anion in alkaline medium under carbon monoxide

Abstract

The reactions of (E)- and (Z)-β-bromostyrene (1a) with dicarbonyldicyanonickelate(0) anion generated in situ in the presence of sodium or calcium hydroxide under carbon monoxide gave a carbonylated product mixture of (E)-cinnamic acid [(E)-(2a)], 3,4-diphenylhexanedioic acid (4), and 3-phenylpropionic acid (5). In contrast, in the reactions of α-methyl- and phenyl-β-bromostyrenes (1b and c) the corresponding nitriles (3b and c) were formed, together with the carboxylic acids (2b and c).