Stable phosphonium sila-ylide with reactivity as a sila-Wittig reagent

J Am Chem Soc. 2009 Jul 1;131(25):8762-3. doi: 10.1021/ja903540b.

Abstract

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.