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Synlett 2007(1): 0091-0094
DOI: 10.1055/s-2006-958413
DOI: 10.1055/s-2006-958413
LETTER
© 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
Further Information
Received
4 September 2006
Publication Date:
20 December 2006 (online)
Publication History
Publication Date:
20 December 2006 (online)
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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
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