Synthesis 2014; 46(19): 2608-2616
DOI: 10.1055/s-0034-1378318
paper
© Georg Thieme Verlag Stuttgart · New York

Tandem Thioetherification Reactions of 2-(2,2-Dibromovinyl)phenol Derivatives with Thiophenols and Thiols

Haobing Geng
a   Department of Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China   eMail: zhxiuli@163.com
,
Juan Du
a   Department of Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China   eMail: zhxiuli@163.com
,
Shanshan Chen
a   Department of Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China   eMail: zhxiuli@163.com
,
Qinghua Huang
a   Department of Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China   eMail: zhxiuli@163.com
,
Xiuli Zhang*
a   Department of Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China   eMail: zhxiuli@163.com
b   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
,
Lei Wang*
b   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
c   Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China   eMail: leiwang@chnu.edu.cn   Fax: +86(561)3090518
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Publikationsverlauf

Received: 26. März 2014

Accepted after revision: 22. Mai 2014

Publikationsdatum:
24. Juni 2014 (online)


Abstract

A tandem thioetherification reaction of 2-(2,2-dibromovinyl)phenol derivatives with thiophenols and thiols has been developed. In the presence of potassium hydroxide, 2-(2,2-dibromovinyl)phenols reacted with thiophenols and thiols to generate 2-arylthiobenzofurans and 2-alkylthiobenzofurans in good yields in N,N-dimethylformamide via a one-pot tandem reaction. This method has several advantages including commercial availability of starting materials, simple operation, and easy purification of products.

Supporting Information