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Arylcarboxylation of unactivated alkenes with CO(2) via visible-light photoredox catalysis

Photocatalytic carboxylation of alkenes with CO(2) 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...

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Detalles Bibliográficos
Autores principales: Zhang, Wei, Chen, Zhen, Jiang, Yuan-Xu, Liao, Li-Li, Wang, Wei, Ye, Jian-Heng, Yu, Da-Gang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10267151/
https://www.ncbi.nlm.nih.gov/pubmed/37316537
http://dx.doi.org/10.1038/s41467-023-39240-8
Descripción
Sumario:Photocatalytic carboxylation of alkenes with CO(2) 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 CO(2), 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.