Synfacts 2007(5): 0533-0533  
DOI: 10.1055/s-2007-968422
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Vinylstannanes from Ketones

Contributor(s): Paul Knochel, Andrei Gavryushin
A. Darwish, J. M. Chong*
University of Waterloo, Canada
Further Information

Publication History

Publication Date:
24 April 2007 (online)


Vinylstannanes are extremely useful synthetic intermediates and convenient precursors to vinyllithium species or in Pd-catalyzed Stille cross-coupling reactions. Several methods for the conversion of ketones into vinylstannanes have been reported but this publication describes the most simple, general, and high-yielding protocol for this transformation. In the case of substituted cycloalkylketones, only one product regioisomer is formed. The authors also described a useful procedure for the removal of the excess of Bu3SnH from reaction mixtures using AIBN×CHCl3.