Stable phosphonium sila-ylide with reactivity as a sila-Wittig reagent.
The silicon congeners of well-known phosphonium ylides have been considered only as short-lived reactive intermediates. We successfully synthesized a remarkably stable phosphonium sila-ylide. Its X-ray structure reveals a long Si-P bond and a strongly pyramidalized silicon center, indicating a very weak P-Si pi interaction. In addition, it exhibits an alpha,beta-ambiphilic character with a nucleophilic silicon center, similar to its carbon-congener phosphonium ylides. This property of the phosphonium sila-ylide allows its use as a sila-Wittig reagent with carbonyl derivatives.
Gau
David
D
Universite de Toulouse, UPS, LHFA, and CNRS, LHFA UMR 5069, F-31062 Toulouse, France.
Kato
Tsuyoshi
T
Saffon-Merceron
Nathalie
N
Cossío
Fernando P
FP
Baceiredo
Antoine
A