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Synthesis 2010(21): 3602-3608  
DOI: 10.1055/s-0030-1258234
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Copper-Catalyzed S-Arylation of Thiols with Aryl Bromides and Chlorides

Yaming Li*, Xiaoying Li, Huifeng Wang, Tao Chen, Yusheng Xie
State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116012, P. R. of China
Fax: +86(411)39893900; e-Mail: yamingli@chem.dlut.edu.cn;
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Publication History

Received 8 June 2010
Publication Date:
30 August 2010 (online)

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Abstract

An efficient copper-catalyzed system for C-S cross-coupling­ of aromatic thiols with aryl bromides and chlorides has been developed using 1,2,3,4-tetrahydroquinoline-8-ol as a ligand. It is noteworthy that this method is proved to be especially effective for aryl bromides with electron-donating groups. By this protocol, a variety of thioethers as well as symmetrical and unsymmetrical bis-thioethers are obtained in excellent yields with an exceptional level of functional group tolerance and high chemoselectivity.

Key words

copper catalyst - aryl bromides - aryl chlorides - cross-coupling - organic sulfides