Regioselective Heck Vinylation of Electron-Rich Olefins with Vinyl Halides: Is the Neutral Pathway in Operation?

作者:McConville Matthew; Saidi Ourida; Blacker John; Xiao Jianliang*
来源:Journal of Organic Chemistry, 2009, 74(7): 2692-2698.
DOI:10.1021/jo802781m

摘要

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 contrast to the related arylation reaction, evidence suggests that the vinylation may proceed via the neutral Heck mechanism.

  • 出版日期2009-4-3