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

Haobing Geng; Juan Du; Shanshan Chen; Qinghua Huang; Xiuli Zhang; Lei Wang

doi:10.1055/s-0034-1378318

Synthesis, Table of Contents

Synthesis 2014; 46(19): 2608-2616
DOI: 10.1055/s-0034-1378318

paper

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

Haobing Geng

^aDepartment of Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China Email: zhxiuli@163.com

,

Juan Du

^aDepartment of Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China Email: zhxiuli@163.com

,

Shanshan Chen

^aDepartment of Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China Email: zhxiuli@163.com

,

Qinghua Huang

^aDepartment of Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China Email: zhxiuli@163.com

,

Xiuli Zhang*

^aDepartment of Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China Email: zhxiuli@163.com

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China

,

Lei Wang*

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China

^cDepartment 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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Abstract

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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.

Key words

2-arylthiobenzofurans - 2-alkylthiobenzofurans - 2-(2,2-dibromovinyl)phenols - tandem reactions - thiols - thiophenols

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References

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