Construction of Functionalized Oxindoles by Quinone-Carbonate Synergistically Triggered Intermolecular Radical Coupling

We disclose a rapid and nontoxic procedure to construct various oxindoles. This method harnesses the power of a catalytic amount of quinone in synergy with Cs2CO3, showcasing remarkable compatibility with a wide range of functional groups. Mechanistic investigations reveal that it operates via a rad...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-09, Vol.89 (17), p.12753-12761
Main Authors: Qiu, Yun, Wu, Zecheng, Ou, Xingyun, Zhao, Qiuting, Lei, Hao, Wang, Chengming
Format: Article
Language:English
Subjects:
electron transfer
organic chemistry
quinones
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Summary:We disclose a rapid and nontoxic procedure to construct various oxindoles. This method harnesses the power of a catalytic amount of quinone in synergy with Cs2CO3, showcasing remarkable compatibility with a wide range of functional groups. Mechanistic investigations reveal that it operates via a radical pathway, likely initiated by the single-electron transfer from quinone-Cs2CO3 complexes. This pivotal electron transfer event leads to the generation of a crucial alkyl radical intermediate, contributing to the overall success and efficacy of the transformation.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01150