Affordable Access

A chemoselective reduction of alkynes to (E)-alkenes.

Authors
  • Trost, Barry M
  • Ball, Zachary T
  • Jöge, Thomas
Type
Published Article
Journal
Journal of the American Chemical Society
Publication Date
Jul 10, 2002
Volume
124
Issue
27
Pages
7922–7923
Identifiers
PMID: 12095335
Source
Medline
License
Unknown

Abstract

The trans reduction of all types of alkynes to give (E)-olefins is achieved through a two-stage trans hydrosilylation and protodesilylation. Reaction of an alkyne and a silane with the ruthenium catalyst [Cp*Ru(MeCN)3]PF6 results in clean hydrosilylation to give only the (Z)-trans addition product at ambient temperature with catalyst loadings of 1-5 mol %. The crude vinylsilane products are then protodesilylated by the action of cuprous iodide and TBAF at rt-35 degrees C. The reaction is compatible with many sensitive functional groups and provides a general trans-alkyne reduction not possible by other means.

Report this publication

Statistics

Seen <100 times