Photoinduced Deoxygenation Reduction of Sulfoxides with HCl or HBr and Hydrocarbons

The deoxygenative reduction of sulfoxides to thioethers represents one of the most important transformations in organic synthesis, garnering significant attention in both academic research and industrial applications. Herein, we report a photoinduced deoxygenative reduction of sulfoxides using inexpensive hydrocarbon species and HX (X = Cl, Br) as combined reductants, which proceeds under mild conditions without the photocatalysts and metals. Mechanistically, this transformation is enabled by a proton-coupled electron transfer process between the S<sup>IV</sup>═O group and HX. This protocol exhibits a broad substrate scope, excellent functional group tolerance, and operational simplicity.

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Publication Details

Journal
Organic Letters
Published
2025-12-24
DOI
https://doi.org/10.1021/acs.orglett.5c05186
Citations
1
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.94
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article

Photoinduced Deoxygenation Reduction of Sulfoxides with HCl or HBr and Hydrocarbons

Zemin Wang, Dayong Shi, Feng Xu
1 citations
Organic Letters
Sulfur-Based Synthesis Techniques
0.94
article

Photoinduced Deoxygenation Reduction of Sulfoxides with HCl or HBr and Hydrocarbons

Zemin Wang, Dayong Shi, Feng Xu
article en
1 citations

Abstract

The deoxygenative reduction of sulfoxides to thioethers represents one of the most important transformations in organic synthesis, garnering significant attention in both academic research and industrial applications. Herein, we report a photoinduced deoxygenative reduction of sulfoxides using inexpensive hydrocarbon species and HX (X = Cl, Br) as combined reductants, which proceeds under mild conditions without the photocatalysts and metals. Mechanistically, this transformation is enabled by a proton-coupled electron transfer process between the S<sup>IV</sup>═O group and HX. This protocol exhibits a broad substrate scope, excellent functional group tolerance, and operational simplicity.

Organic LettersVol. 28(1)
Qingdao University (CN), Shandong University (CN), Affiliated Hospital of Qingdao University (CN), State Key Laboratory of Microbial Technology
Openalex Percentile: Top 19%
Sulfur-Based Synthesis Techniques
0.94
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