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

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• 作者：Matthew McConville ; Ourida Saidi ; John Blacker ; Jianliang Xiao
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：April 3, 2009
• 年：2009
• 卷：74
• 期：7
• 页码：2692-2698
• 全文大小：244K
• 年卷期：v.74,no.7(April 3, 2009)
• ISSN：1520-6904

文摘

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.