Arylcarboxylation of unactivated alkenes with CO2 via visible-light photoredox catalysis

Wei Zhang, Zhen Chen, Yuan-Xu Jiang, Li-Li Liao, Wei Wang, Jian-Heng Ye () and Da-Gang Yu ()
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Wei Zhang: Sichuan University
Zhen Chen: Sichuan University
Yuan-Xu Jiang: Sichuan University
Li-Li Liao: Chongqing University
Wei Wang: Sichuan University
Jian-Heng Ye: Sichuan University
Da-Gang Yu: Sichuan University

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract Photocatalytic carboxylation of alkenes with CO2 is a promising and sustainable strategy to synthesize high value-added carboxylic acids. However, it is challenging and rarely investigated for unactivated alkenes due to their low reactivities. Herein, we report a visible-light photoredox-catalyzed arylcarboxylation of unactivated alkenes with CO2, delivering a variety of tetrahydronaphthalen-1-ylacetic acids, indan-1-ylacetic acids, indolin-3-ylacetic acids, chroman-4-ylacetic acids and thiochroman-4-ylacetic acids in moderate-to-good yields. This reaction features high chemo- and regio-selectivities, mild reaction conditions (1 atm, room temperature), broad substrate scope, good functional group compatibility, easy scalability and facile derivatization of products. Mechanistic studies indicate that in situ generation of carbon dioxide radical anion and following radical addition to unactivated alkenes might be involved in the process.

Date: 2023
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DOI: 10.1038/s41467-023-39240-8

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