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Synlett 2019; 30(19): 2181-2184
DOI: 10.1055/s-0039-1690221
letter
© Georg Thieme Verlag Stuttgart · New York

Copper(I)-Catalyzed Sulfenylation of 1,3-Dicarbonyl Substrates with Disulfides under Mild Conditions

Jingnan Zhao
a   State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, P. R. of China   Email: mengqw@dlut.edu.cn
,
Fan Yang
b   Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116024, P. R. of China
,
Zongyi Yu
a   State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, P. R. of China   Email: mengqw@dlut.edu.cn
,
Xiaofei Tang
a   State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, P. R. of China   Email: mengqw@dlut.edu.cn
,
Yufeng Wu
a   State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, P. R. of China   Email: mengqw@dlut.edu.cn
,
Cunfei Ma
a   State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, P. R. of China   Email: mengqw@dlut.edu.cn
,
Qingwei Meng∗
a   State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, P. R. of China   Email: mengqw@dlut.edu.cn
› Author AffiliationsWe would like to thank the National Natural Science Foundation of China (grant numbers 21476041, U1608224, 61633006) and the State Key Laboratory of Fine Chemicals for their support.
Further Information

Publication History

Received: 28 August 2019

Accepted after revision: 10 October 2019

Publication Date:
23 October 2019 (online)

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Abstract

A copper(I) iodine catalyzed sulfenylation of 1,3-dicarbonyl substrates in the presence of MeCN is presented. Various β-keto esters and β-keto amide substrates can react with disulfides to afford their corresponding products in good to excellent yields. The notable features of this protocol include high atom economy, easy operation, mild reaction conditions, and excellent functional group tolerance.

Key words

sulfenylation - disulfides - copper(I) iodide - β-keto esters - MeCN

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690221.
  • Supporting Information
 

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