Photo-Fenton-Like (Trideutero)methylsulfonylation/Remote (Benzo)thiazolyl Migration Cascade of Unactivated Alkenes with DMSO(- <i>d</i> <sub>6</sub> )

We report a visible-light photocatalytic, transition-metal-free methylsulfonylation/distal (benzo)thiazolyl migration cascade of unactivated alkenes using DMSO or DMSO- d 6 as methylsulfonyl or trideuteromethylsulfonyl sources. The corresponding sulfonyl radicals add selectively to the terminal alkene carbon and trigger distal migration. Mechanistic studies support hydroxyl-radical generation through a photo-Fenton-like process involving water and oxygen, without externally added hydrogen peroxide, thereby avoiding metal leaching and catalyst deactivation.

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Publication Details

Journal
Organic Letters
Published
2026-07-22
DOI
https://doi.org/10.1021/acs.orglett.6c02449
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Photo-Fenton-Like (Trideutero)methylsulfonylation/Remote (Benzo)thiazolyl Migration Cascade of Unactivated Alkenes with DMSO(- d 6 )

Q F Liu, Yang Zm, H L Liu, Guanghui Lv et al.
Organic Letters
Radical Photochemical Reactions
article

Photo-Fenton-Like (Trideutero)methylsulfonylation/Remote (Benzo)thiazolyl Migration Cascade of Unactivated Alkenes with DMSO(- d 6 )

Q F Liu, Yang Zm, H L Liu, Guanghui Lv, Tianle Huang, Hui Li, Zhihang Tang, Yan Wu, R Wang, Shengqing Yu, Hui Song
article en

Abstract

We report a visible-light photocatalytic, transition-metal-free methylsulfonylation/distal (benzo)thiazolyl migration cascade of unactivated alkenes using DMSO or DMSO- d 6 as methylsulfonyl or trideuteromethylsulfonyl sources. The corresponding sulfonyl radicals add selectively to the terminal alkene carbon and trigger distal migration. Mechanistic studies support hydroxyl-radical generation through a photo-Fenton-like process involving water and oxygen, without externally added hydrogen peroxide, thereby avoiding metal leaching and catalyst deactivation.

Organic Letters
Hubei University of Medicine (CN), US Forest Service (US), Ministry of Education of the People's Republic of China (CN), Sichuan University (CN), West China Hospital of Sichuan University (CN), Taihe Hospital (CN), The Medical Device (United Kingdom) (GB), Pharmaceuticals and Medical Devices Agency (JP)
Openalex Percentile: Top 15%
Radical Photochemical Reactions
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