Visible-Light-Driven Thiolate-Catalyzed Carbo-Carboxylation of Alkenes with CO2: Facile Synthesis of Oxindole-3-acetic Acid Derivatives

You-Yang Jiang , Zhen Chen , Yuan-Xu Jiang , Wen-Jing Zhu , Jin-Cheng Xu , Jian-Heng Ye , Wei Zhang , Da-Gang Yu

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (18) : 2341 -2346.

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Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (18) : 2341 -2346. DOI: 10.1002/cjoc.70115
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Visible-Light-Driven Thiolate-Catalyzed Carbo-Carboxylation of Alkenes with CO2: Facile Synthesis of Oxindole-3-acetic Acid Derivatives

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Abstract

Herein, we present a visible-light-driven carbo-carboxylation of alkenes with CO2 via catalytic electron donor-acceptor (EDA) complex activation. A variety of oxindole-3-acetic acid and derivatives were generated in moderate to excellent yields from N-arylacrylamides and CO2. Mechanistic studies revealed the formation of an EDA complex between catalytic thiolate and alkene. Notably, this redox-neutral reaction features mild, transition-metal and photocatalyst-free conditions, good functional group tolerance and broad substrate scope. Furthermore, the facile synthesis of key intermediates in natural products underscores the utility of this methodology.

Keywords

Carbon dioxide / Visible light / Carbo-carboxylation / Electron donor-acceptor (EDA) complex / Oxindole-3-acetic acid derivatives / N-Arylacrylamides / Thiolate

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You-Yang Jiang, Zhen Chen, Yuan-Xu Jiang, Wen-Jing Zhu, Jin-Cheng Xu, Jian-Heng Ye, Wei Zhang, Da-Gang Yu. Visible-Light-Driven Thiolate-Catalyzed Carbo-Carboxylation of Alkenes with CO2: Facile Synthesis of Oxindole-3-acetic Acid Derivatives. Chinese Journal of Chemistry, 2025, 43(18): 2341-2346 DOI:10.1002/cjoc.70115

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2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH

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