LETTER	Synlett 2007: 0091-0094   DOI: 10.1055/s-2006-958413
© Georg Thieme Verlag Stuttgart · New York
Mild, Efficient and Highly Stereoselective Synthesis of (Z)-Vinyl Chalcogenides from Vinyl Bromides Catalyzed by Copper(I) in Ionic Liquids Based on Amino Acids
Zhiming Wang, Hanjie Mo, Weiliang Bao*
Department of Chemistry, Zhejiang University, Xi Xi Campus, Hangzhou, Zhejiang 310028, P. R. of China Fax: +86(571)88273814; e-Mail: wlbao@css.zju.edu.cn;
Received 4 September 2006

Abstract

A method for the synthesis of (Z)-vinyl chalcogenides by the coupling of vinyl bromides with thiols or diphenyl diselenide using copper(I) salts as catalysts in ionic liquids based on amino ­acids is reported. The desired vinyl chalcogenides were obtained in good to excellent yields with retention of stereochemistry. The ionic liquids play multiple roles in the reaction: they act as solvent, base, and excellent promoter for the copper-catalyzed coupling reactions.

Key words

ionic liquids - copper - coupling - stereoselective - vinyl chalcogenides