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Synthesis 2012(3): 380-388  
DOI: 10.1055/s-0031-1290067
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis of (Z)-1,2-Dithio-1-alkenes via Copper-Catalyzed Thiolation of (Z)-2-Bromovinyl Sulfides

Hui Xua, Wanzhi Chen*a, Jiuxi Chenb, Huayue Wu*b
a Department of Chemistry, Zhejiang University, Xixi Campus, Hangzhou 310028, P. R. of China
Fax: +86(571)88273314; e-Mail: chenwzz@zju.edu.cn;
b College of Chemistry & Material Engineering, Wenzhou University, Wenzhou 325035, P. R. of China
e-Mail: hywu3@163.com;
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Publication History

Received 31 October 2011
Publication Date:
03 January 2012 (online)

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Abstract

We describe a new method for the stereoselective synthesis of (Z)-1,2-dithio-1-alkenes via copper-catalyzed cross-coupling of (Z)-2-bromovinyl sulfides and thiols. The desired products are obtained in good to excellent yields. The double bond geometry of the starting (Z)-2-bromovinyl sulfides is retained under these reaction conditions.

Key words

copper catalyst - cross-coupling - thiolation - (Z)-2-bromovinyl sulfide - (Z)-1,2-dithio-1-alkene