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Stereoselective Hydrothiolation of Alkynes Catalyzed by Cesium Base: Facile Access to (Z)-1-Alkenyl Sulfides

Azusa Kondoh, Kazuaki Takami, Hideki Yorimitsu* and Koichiro Oshima

*Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku Katsura, Nishikyo-ku, Kyoto 615-8510, Japan, Email:

A. Kondoh, K. Takami, H. Yorimitsu, K. Oshima, J. Org. Chem., 2005, 70, 6468-6473.

DOI: 10.1021/jo050931z


The reaction of an alkyne with an alkanethiol in the presence of a catalytic amount of cesium carbonate and TEMPO as a radical inhibitor in DMSO provides the corresponding 1-alkenyl alkyl sulfide adduct in good yield with high Z-selectivity.

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Key Words

Vinyl sulfides

ID: J42-Y2005-1030