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.,Munday, Rachel H.
p. 8971 - 8974
(2007/10/03)
The direct use of phenyldimethylsilanes in silicon assisted palladium catalysed cross coupling
A vinyl-phenylsilane has been used as a masked vinyl organometallic for a cross coupling reaction with phenyl iodide to provide the cine substitution product in high yield.
Anderson, James C.,Anguille, Stephane,Bailey, Rosalyn
p. 2018 - 2019
(2007/10/03)
Strategies for protodesilylation of C-2 trialkylsilyl terminal alkenes
The mild and high yielding protodesilylation of C-2 trialkylsilyl terminal alkenes can be effected via a hydroboration-Peterson elimination protocol or, in the case of the phenyldimethylsilyl analogues, a one pot procedure using t-BuOK-18-C-6-TBAF can be used. The Royal Society of Chemistry 2000.
Anderson, James C.,Flaherty, Alice
p. 3025 - 3027
(2007/10/03)
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