Photoinduced 1,2-Carbosulfenylation of Alkenes

Herein, we report a mild, efficient photocatalytic protocol for 1,2-carbosulfenylation of alkenes using <i>N</i>-hydroxyphthalimide esters as carbon sources and alkyl thiosulfate salts as sulfur sources. This operationally simple methodology provides a novel avenue for synthesizing dialkylthioether, including methylthioether, derivatives. The reaction has a broad substrate scope and excellent functional group tolerance. Mechanistic studies have elucidated the mechanism and confirmed the preferential participation of alkyl radicals in the reaction, producing the highly regioselective 1,2-carbosulfenylation of alkenes.

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Publication Details

Journal
Organic Letters
Published
2025-05-28
DOI
https://doi.org/10.1021/acs.orglett.5c01741
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.00

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article

Photoinduced 1,2-Carbosulfenylation of Alkenes

Yu Lu, Xiao‐Hui Yang, Zihang Peng, Chen Ling et al.
Organic Letters
Sulfur-Based Synthesis Techniques
article

Photoinduced 1,2-Carbosulfenylation of Alkenes

Yu Lu, Xiao‐Hui Yang, Zihang Peng, Chen Ling, Xuebin Huang
article en

Abstract

Herein, we report a mild, efficient photocatalytic protocol for 1,2-carbosulfenylation of alkenes using <i>N</i>-hydroxyphthalimide esters as carbon sources and alkyl thiosulfate salts as sulfur sources. This operationally simple methodology provides a novel avenue for synthesizing dialkylthioether, including methylthioether, derivatives. The reaction has a broad substrate scope and excellent functional group tolerance. Mechanistic studies have elucidated the mechanism and confirmed the preferential participation of alkyl radicals in the reaction, producing the highly regioselective 1,2-carbosulfenylation of alkenes.

Organic LettersVol. 27(22)
Beijing Institute of Technology (CN), Ministry of Industry and Information Technology (CN)
National Natural Science Foundation of China, National Key Research and Development Program of China
Openalex Percentile: Top 91%
Sulfur-Based Synthesis Techniques
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Photoinduced 1,2-Carbosulfenylation of Alkenes — Yu Lu, Xiao‐Hui Yang, et al. · Organic Letters (2025) | TGRS Research Map | TGRS