Photocatalytic Fluoroalkylative Cyclization of o -Alkenylbenzamides Enabled by Fluoroalkylsulfonyl Chlorides

Photocatalytic fluoroalkylative cyclization of alkenes provides an efficient approach to fluorinated heterocycles, yet existing methods generally require distinct radical precursors for different fluoroalkyl groups. Herein, we report a visible-light-induced ruthenium-catalyzed fluoroalkylative cyclization of o-alkenylbenzamides using readily available fluoroalkylsulfonyl chlorides as a unified family of radical precursors. This protocol enables the efficient synthesis of a broad range of fluoroalkylated iminoisobenzofurans bearing trifluoromethyl, difluoromethyl, and perfluoroalkyl substituents under mild conditions with a broad substrate scope and good functional group compatibility. Mechanistic studies support a photocatalytic radical pathway initiated by single-electron reduction of the fluoroalkylsulfonyl chlorides.

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Journal
The Journal of Organic Chemistry
Published
2026-11-06
DOI
https://doi.org/10.1021/acs.joc.6c02108
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Photocatalytic Fluoroalkylative Cyclization of o -Alkenylbenzamides Enabled by Fluoroalkylsulfonyl Chlorides

Xi-Tao Li, Xue-Juan Huang, Qi-Yu Zhong, Xiao-Na Zhu et al.
5 links
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Photocatalytic Fluoroalkylative Cyclization of o -Alkenylbenzamides Enabled by Fluoroalkylsulfonyl Chlorides

Xi-Tao Li, Xue-Juan Huang, Qi-Yu Zhong, Xiao-Na Zhu, Ze-Tian Li, Yu Long, Xian-Ze Duan
article en

Abstract

Photocatalytic fluoroalkylative cyclization of alkenes provides an efficient approach to fluorinated heterocycles, yet existing methods generally require distinct radical precursors for different fluoroalkyl groups. Herein, we report a visible-light-induced ruthenium-catalyzed fluoroalkylative cyclization of o-alkenylbenzamides using readily available fluoroalkylsulfonyl chlorides as a unified family of radical precursors. This protocol enables the efficient synthesis of a broad range of fluoroalkylated iminoisobenzofurans bearing trifluoromethyl, difluoromethyl, and perfluoroalkyl substituents under mild conditions with a broad substrate scope and good functional group compatibility. Mechanistic studies support a photocatalytic radical pathway initiated by single-electron reduction of the fluoroalkylsulfonyl chlorides.

The Journal of Organic Chemistry
Sun Yat-sen University (CN)
Science and Technology Foundation of Shenzhen City, Sun Yat-sen University, Fundamental Research Funds for the Central Universities
Openalex Percentile: Top 27%
Radical Photochemical Reactions
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