Visible-Light Photoredox-Catalyzed Synthesis of Phosphorylated γ-Sultines via Radical-Polar Crossover Cyclization

A three-component cascade radical addition/SO 2 incorporation/5-exo -tet cyclization of alkenes with secondary phosphine oxides and DABCO·(SO 2 ) 2 has been developed via visible-light-induced photoredox catalysis. Under mild and operationally simple conditions, a diverse range of phosphorylated γ-sultines were afforded in moderate to good yields. Furthermore, this reaction features high diastereoselectivity, a broad substrate scope, and good functional group tolerance. Further transformations of phosphorylated γ-sultine products demonstrate the potential applications of this approach. Preliminary mechanism studies indicate that this reaction likely proceeds through a radical-polar crossover cyclization.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-06-25
DOI
https://doi.org/10.1021/acs.joc.6c01087
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Visible-Light Photoredox-Catalyzed Synthesis of Phosphorylated γ-Sultines via Radical-Polar Crossover Cyclization

Li, Zhong-Yan Cao, Jiabin Liao, Rongzao Yang et al.
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Visible-Light Photoredox-Catalyzed Synthesis of Phosphorylated γ-Sultines via Radical-Polar Crossover Cyclization

Li, Zhong-Yan Cao, Jiabin Liao, Rongzao Yang, Wei Ding
article en

Abstract

A three-component cascade radical addition/SO 2 incorporation/5-exo -tet cyclization of alkenes with secondary phosphine oxides and DABCO·(SO 2 ) 2 has been developed via visible-light-induced photoredox catalysis. Under mild and operationally simple conditions, a diverse range of phosphorylated γ-sultines were afforded in moderate to good yields. Furthermore, this reaction features high diastereoselectivity, a broad substrate scope, and good functional group tolerance. Further transformations of phosphorylated γ-sultine products demonstrate the potential applications of this approach. Preliminary mechanism studies indicate that this reaction likely proceeds through a radical-polar crossover cyclization.

The Journal of Organic Chemistry
Nanjing Forestry University (CN), Henan University (CN), Zhengzhou University (CN), Chemical Synthesis Lab (SG)
National Natural Science Foundation of China, China Postdoctoral Science Foundation, Henan Provincial Science and Technology Research Project
Openalex Percentile: Top 13%
Radical Photochemical Reactions
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Visible-Light Photoredox-Catalyzed Synthesis of Phosphorylated γ-Sultines via Radical-Polar Crossover Cyclization — Li, Zhong-Yan Cao, et al. · The Journal of Organic Chemistry (2026) | TGRS Research Map | TGRS