Photoredox Iron-Catalyzed Decarboxylative Radical Cyclization for the Synthesis of Oxindoles and Chroman-4-ones

A sustainable, photocatalytic approach for the synthesis of oxindoles and chroman-4-ones was developed using carboxylate salts as radical precursors and FeCl<sub>3</sub> as a catalyst. The reaction proceeds via a decarboxylative radical cyclization mechanism triggered by ligand-to-metal charge transfer under visible light irradiation, operating efficiently at room temperature. This method demonstrates excellent substrate scope, including the use of various alkyl carboxylates, and functional group tolerance and offers a scalable pathway for gram-scale synthesis, highlighting its practical application.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-05-15
DOI
https://doi.org/10.1021/acs.joc.5c00669
Citations
7
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
6.55

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article

Photoredox Iron-Catalyzed Decarboxylative Radical Cyclization for the Synthesis of Oxindoles and Chroman-4-ones

Zhenlu Shen, Meichao Li, Qun Cao, S.H. Han et al.
7 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
6.55
article

Photoredox Iron-Catalyzed Decarboxylative Radical Cyclization for the Synthesis of Oxindoles and Chroman-4-ones

Zhenlu Shen, Meichao Li, Qun Cao, S.H. Han, Litao Liu, J.B. Meng
article en
7 citations

Abstract

A sustainable, photocatalytic approach for the synthesis of oxindoles and chroman-4-ones was developed using carboxylate salts as radical precursors and FeCl<sub>3</sub> as a catalyst. The reaction proceeds via a decarboxylative radical cyclization mechanism triggered by ligand-to-metal charge transfer under visible light irradiation, operating efficiently at room temperature. This method demonstrates excellent substrate scope, including the use of various alkyl carboxylates, and functional group tolerance and offers a scalable pathway for gram-scale synthesis, highlighting its practical application.

The Journal of Organic ChemistryVol. 90(21)
University of Leicester (GB), Zhejiang University of Technology (CN)
National Natural Science Foundation of China, Engineering and Physical Sciences Research Council
Openalex Percentile: Top 3%
Radical Photochemical Reactions
6.55
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