Vinyldimethylphenylsilanes as safety catch silanols in fluoride-free palladium-catalyzed cross-coupling reactions.
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.
Anderson
James C
JC
School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, United Kingdom. j.anderson@nottingham.ac.uk
Munday
Rachel H
RH