Photo‐Induced Sulfonylation/Trifluoromethylation‐Peroxidation of Alkenes via EnT‐Mediated <i>N</i>−S Bond Homolysis of <i>N</i>‐Sulfonyl Ketimines

Abstract Photocatalytic sulfonylation/trifluoromethylation‐peroxidation of alkenes with N ‐sulfonyl ketimines and tert ‐butyl hydroperoxide is reported. The transformation is initiated by the EnT‐driven homolytic S− N bond cleavage of N ‐sulfonyl ketimines. The sulfonyl‐peroxides were obtained when alkyl sulfonyl radicals were captured by alkene via sequential C−S and C−O bond formation, while a thermodynamically favored release of SO 2 from trifluoromethane sulfonyl radical generated CF 3 radical and afforded the trifluoromethyl‐peroxides.

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Publication Details

Journal
Asian Journal of Organic Chemistry
Published
2024-09-02
DOI
https://doi.org/10.1002/ajoc.202400384
Citations
4
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
1.00

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article

Photo‐Induced Sulfonylation/Trifluoromethylation‐Peroxidation of Alkenes via EnT‐Mediated N−S Bond Homolysis of N‐Sulfonyl Ketimines

Yuting Feng, Leiyang Lv, Zhiping Li
4 citations
Asian Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
1.00
article

Photo‐Induced Sulfonylation/Trifluoromethylation‐Peroxidation of Alkenes via EnT‐Mediated N−S Bond Homolysis of N‐Sulfonyl Ketimines

Yuting Feng, Leiyang Lv, Zhiping Li
article en
4 citations

Abstract

Abstract Photocatalytic sulfonylation/trifluoromethylation‐peroxidation of alkenes with N ‐sulfonyl ketimines and tert ‐butyl hydroperoxide is reported. The transformation is initiated by the EnT‐driven homolytic S− N bond cleavage of N ‐sulfonyl ketimines. The sulfonyl‐peroxides were obtained when alkyl sulfonyl radicals were captured by alkene via sequential C−S and C−O bond formation, while a thermodynamically favored release of SO 2 from trifluoromethane sulfonyl radical generated CF 3 radical and afforded the trifluoromethyl‐peroxides.

Asian Journal of Organic ChemistryVol. 13(12)
Renmin University of China (CN)
National Natural Science Foundation of China, Renmin University of China, Fundamental Research Funds for the Central Universities
Openalex Percentile: Top 27%
Sulfur-Based Synthesis Techniques
1.00
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