Vinyldimethylphenylsilanes as Safety Catch Silanols in Fluoride-Free Palladium-Catalyzed Cross-Coupling Reactions
- 9 November 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (25) , 8971-8974
- https://doi.org/10.1021/jo048746t
Abstract
A series of five structurally diverse vinyldimethylphenylsilanes have been shown to undergo a fluoride-free one-pot palladium-catalyzed cross-coupling reaction with phenyl iodide to give ipso coupled products in 62−86% yield. The limitations of this present protocol lie in the activation of Si−Ph vs protodesilylation by KOTMS/18-C-6, which seems sensitive to the sterics of cis substituents, but not geminal substituents.Keywords
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