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Synthesis 2012; 44(6): 966-972
DOI: 10.1055/s-0031-1290246
paper
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Thiolation Cyclization of 1-Chloro-1,5-enynes with Sodium Hydrosulfide: Synthesis of CF3-Containing 1H-Isothiochromenes

Shuai Shi
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China, Fax: +86(577)86689615   Email: zxg@wzu.edu.cn
,
Lei-Lei Sun
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China, Fax: +86(577)86689615   Email: zxg@wzu.edu.cn
,
Zhi-Yong Liao
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China, Fax: +86(577)86689615   Email: zxg@wzu.edu.cn
,
Xing-Guo Zhang*
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China, Fax: +86(577)86689615   Email: zxg@wzu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 12 December 2011

Accepted after revision: 17 January 2012

Publication Date:
24 February 2012 (online)

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Abstract

A copper-catalyzed regio- and stereoselective 6-exo-dig cyclization of 1-chloro-1,5-enynes with sodium hydrosulfide has been developed. In the presence of copper(I) iodide and sodium tert-butoxide, a variety of (Z)-1-methylene-3-(trifluoromethyl)-1H-isothiochromenes were prepared in moderate to good yields via thiolation cyclization of 1-alkynyl-2-(2-chloro-3,3,3-trifluoroprop-1-enyl)benzenes with sodium hydrosulfide.

Key words

copper - thiolation - 6-exo-dig cyclization - 1H-isothiochromenes - sodium hydrosulfide

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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