4.7 Article

A new, efficient method for direct α-alkenylation of β-dicarbonyl compounds and phenols using alkenyltriarylbismuthonium salts

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 69, Issue 16, Pages 5505-5508

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo0492721

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Direct alpha-alkenylation of beta-keto esters, beta-diketone, and phenols with alkenyltriarylbismuthonium salts proceeded smoothly in the presence of 1,1,3,3-tetramethylguanidine to afford the corresponding alpha-alkenylated carbonyl compounds (beta,gamma-unsaturated carbonyl compounds) in good yields. The high leaving ability of the triarylbismuthonio group is a key driving force to achieve the C-C bond formation at the vinylic carbon under mild conditions.

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