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Synlett 2018; 29(03): 364-368
DOI: 10.1055/s-0036-1590925
letter
© Georg Thieme Verlag Stuttgart · New York

Visible-Light-Induced Chemoselective Synthesis of α-Chloro and Vinyl Sulfones by Sulfonylation of Alkenes

Teng-fei Niu  *
School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, Jiangsu Province, P. R. of China   Email: niutf@jiangnan.edu.cn   Email: byron_ni@yeah.net
,
Dan Lin
School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, Jiangsu Province, P. R. of China   Email: niutf@jiangnan.edu.cn   Email: byron_ni@yeah.net
,
Lin-shuang Xue
School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, Jiangsu Province, P. R. of China   Email: niutf@jiangnan.edu.cn   Email: byron_ni@yeah.net
,
Ding-yun Jiang
School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, Jiangsu Province, P. R. of China   Email: niutf@jiangnan.edu.cn   Email: byron_ni@yeah.net
,
Bang-qing Ni*
School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, Jiangsu Province, P. R. of China   Email: niutf@jiangnan.edu.cn   Email: byron_ni@yeah.net
› Author AffiliationsThe authors gratefully acknowledge the Natural Science Foundation of Jiangsu Province, China (BK20160164) for financial support.
Further Information

Publication History

Received: 28 July 2017

Accepted after revision: 11 September 2017

Publication Date:
20 October 2017 (online)

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Abstract

Direct sulfonylation between alkenes and sulfonyl chloride was achieved at room temperature by a visible-light-induced photo­redox process. This method allows the chemoselective synthesis of α-chloro and vinyl sulfone derivatives with moderate to high yields. The selectivity of the reaction was fully controlled by the electronic properties of the alkenes.

Key words

visible-light-induced reaction - atom-transfer radical addition - sulfonylation of alkenes - chemoselectivity - α-Chloro sulfones - vinyl sulfones

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590925.
  • Supporting Information
 

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