Mechanism

Oxidative addition of the Pd(0) with vinyl halide leads to the formation of the intermediate A that with base gives organopalladium alkoxide B. Due to low nucleophilicity of the organoboron, the transmetallation takes place faster with B compared to A to afford the intermediate C that can complete the catalytic cycle by reductive elimination of the target product (Scheme 4).

 

Scheme 4

Examples:

M. Rubina, M. Rubin, V. Geforgyan, J. Am. Chem. Soc . 2003 , 125 , 7198.

A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000 , 127 , 4020 .

Y. Liu, G. W. Gribble, Tetrahedron Lett. 2000 , 41 , 8717.

S. Sakthivel, T. Punniyamurthy, Tetrahedron: Asymmetry 2012 , 23 , 101.