Regioselective Heck vinylation of electron-rich olefins with vinyl halides: is the neutral pathway in operation?

M McConville, O Saidi, J Blacker…

Index: McConville, Matthew; Saidi, Ourida; Blacker, John; Xiao, Jianliang Journal of Organic Chemistry, 2009 , vol. 74, # 7 p. 2692 - 2698

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Citation Number: 35

Abstract

Highly regioselective vinylation of electron-rich olefins by bromo-as well as chlorostyrenes is effected by palladium catalysis with either mono-or bidentate phosphines in a molecular solvent, with no need for halide scavengers, ionic liquids, or ionic additives. The use of the hemilabile 1, 3-bis (diphenylphosphino) propane monoxide (dpppO) as a ligand led to faster reactions of more challenging 2-substituted vinyl ethers and reduced Pd loadings. In ...