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Synlett 2018; 29(15): 2076-2080
DOI: 10.1055/s-0037-1610649
letter
© Georg Thieme Verlag Stuttgart · New York

Transition-Metal-Free Synthesis of Thiosulfonates through Radical Coupling Reaction

◊
Guodong Zhou
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn   Email: guozhiyong@nbu.edu.cn
,
Xu-Dong Xu
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn   Email: guozhiyong@nbu.edu.cn
,
Gan-Ping Chen
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn   Email: guozhiyong@nbu.edu.cn
,
Wen-Ting Wei*
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn   Email: guozhiyong@nbu.edu.cn
b   State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, P. R. of China
,
Zhiyong Guo*
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn   Email: guozhiyong@nbu.edu.cn
› Author AffiliationsThis research is sponsored by the Natural Science Foundation of ­Zhejiang Province (No. LQ18B020002), State Key Laboratory of Analytical Chemistry for Life Science (No. SKLACLS1804), the Open Subject of State Key Laboratory of Chemo/Biosensing and Chemometrics (2017016), Education Foundation of Zhejiang Province (No. Y201737123), and the K. C. Wong Magna Fund in Ningbo University. Prof. Z.Y. Guo also thank the Natural Science Foundation of China (Grants 41576098, 81773483).
Further Information

Publication History

Received: 03 June 2018

Accepted after revision: 03 July 2018

Publication Date:
02 August 2018 (online)

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◊ These authors contributed equally to this work

Abstract

An efficient and practical transition-metal-free radical ­coupling reaction of sulfonyl hydrazides mediated by NIS/K2S2O8 has been developed to afford a variety of biological activity thiosulfonates in moderate to excellent yields. Compared to a known approach for the synthesis of thiosulfonates from sulfonyl hydrazides, this strategy features high yields, mild reaction conditions, and broad substrate scope. The mechanistic studies revealed that the procedure undergoes via a radical cross-coupling process for the construction of S–S bonds.

Keywords

transition-metal-free - radical coupling reaction - S–S bonds - thiosulfonates

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610649.
  • Supporting Information
 

  • References and Notes


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