A copper-catalyzed direct C(sp2)–H alkylsulfonylation of alkenes using alkylsilyl peroxides and DABCO·(SO2)2

Xueni Tian; Lingling Chen; Tonghao Zhu; Jie Wu

doi:10.1039/D3QO01119D

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A copper-catalyzed direct C(sp²)–H alkylsulfonylation of alkenes using alkylsilyl peroxides and DABCO·(SO₂)₂†‡

Xueni Tian,^a Lingling Chen,^a Tonghao Zhu*^a and Jie Wu

*^abc

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* Corresponding authors

^a School of Pharmaceutical and Chemical Engineering & Institute for Advanced Studies, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, China
E-mail: zhuth@tzc.edu.cn, jie_wu@fudan.edu.cn

^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China

^c School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, China

Abstract

A copper-catalyzed direct C(sp²)–H alkylsulfonylation of alkenes using alkylsilyl peroxides and DABCO·(SO₂)₂ was developed, and shown to provide a convenient route to diverse (E)-alkylsulfonyl alkenes. During this transformation, alkylsilyl peroxides were used as the alkyl radical precursors with the insertion of sulfur dioxide. This methodology showed good reaction efficiency, excellent functional group tolerance and stereoselectivity.

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Article information

DOI: https://doi.org/10.1039/D3QO01119D
Article type: Research Article
Submitted: 19 Jul 2023
Accepted: 11 Aug 2023
First published: 11 Aug 2023

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Org. Chem. Front., 2023,10, 4821-4826

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A copper-catalyzed direct C(sp²)–H alkylsulfonylation of alkenes using alkylsilyl peroxides and DABCO·(SO₂)₂

X. Tian, L. Chen, T. Zhu and J. Wu, Org. Chem. Front., 2023, 10, 4821 DOI: 10.1039/D3QO01119D

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