Photoredox-Catalyzed N-Centered Radical-Mediated Cascade Annulation/Dearomatization of <i>ortho</i> -Sulfonamide-Tethered Alkylidenecyclopropanes

-sulfonamide-tethered alkylidenecyclopropanes via N-centered radicals has been developed under metal-free conditions. The reaction employs an organic fluorophore 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as a photocatalyst. This mild and operationally simple photocatalytic system demonstrates that the sulfonamidyl-radical-mediated intramolecular olefin amination effectively integrates radical ring opening with dearomatization pathways, thereby facilitating the synthesis of diverse fused seven-membered cyclic sulfonamides with a broad substrate scope, high regioselectivity, and excellent product diversity.

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Publication Details

Journal
Organic Letters
Published
2026-04-25
DOI
https://doi.org/10.1021/acs.orglett.6c01266
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Photoredox-Catalyzed N-Centered Radical-Mediated Cascade Annulation/Dearomatization of ortho -Sulfonamide-Tethered Alkylidenecyclopropanes

Xuan‐Hui Ouyang, Guobo Deng, Yun Liang, Houyu Mao et al.
Organic Letters
Radical Photochemical Reactions
article

Photoredox-Catalyzed N-Centered Radical-Mediated Cascade Annulation/Dearomatization of ortho -Sulfonamide-Tethered Alkylidenecyclopropanes

Xuan‐Hui Ouyang, Guobo Deng, Yun Liang, Houyu Mao, Zhiqiang Ling, Hong Zou
article en

Abstract

-sulfonamide-tethered alkylidenecyclopropanes via N-centered radicals has been developed under metal-free conditions. The reaction employs an organic fluorophore 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as a photocatalyst. This mild and operationally simple photocatalytic system demonstrates that the sulfonamidyl-radical-mediated intramolecular olefin amination effectively integrates radical ring opening with dearomatization pathways, thereby facilitating the synthesis of diverse fused seven-membered cyclic sulfonamides with a broad substrate scope, high regioselectivity, and excellent product diversity.

Organic LettersVol. 28(18)
Qingdao University of Science and Technology (CN), Hunan Normal University (CN), Ministry of Education (BD), State Key Laboratory of Chemical Engineering (CN), Anhui Normal University (CN), Nanchang Hangkong University (CN)
National Natural Science Foundation of China, Jiangxi Provincial Department of Science and Technology, Anhui Normal University
Openalex Percentile: Top 19%
Radical Photochemical Reactions
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