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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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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
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author Zhang, Wei
Chen, Zhen
Jiang, Yuan-Xu
Liao, Li-Li
Wang, Wei
Ye, Jian-Heng
Yu, Da-Gang
author_facet Zhang, Wei
Chen, Zhen
Jiang, Yuan-Xu
Liao, Li-Li
Wang, Wei
Ye, Jian-Heng
Yu, Da-Gang
author_sort Zhang, Wei
collection PubMed
description 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.
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spelling pubmed-102671512023-06-15 Arylcarboxylation of unactivated alkenes with CO(2) via visible-light photoredox catalysis Zhang, Wei Chen, Zhen Jiang, Yuan-Xu Liao, Li-Li Wang, Wei Ye, Jian-Heng Yu, Da-Gang Nat Commun Article 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. Nature Publishing Group UK 2023-06-14 /pmc/articles/PMC10267151/ /pubmed/37316537 http://dx.doi.org/10.1038/s41467-023-39240-8 Text en © The Author(s) 2023 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Zhang, Wei
Chen, Zhen
Jiang, Yuan-Xu
Liao, Li-Li
Wang, Wei
Ye, Jian-Heng
Yu, Da-Gang
Arylcarboxylation of unactivated alkenes with CO(2) via visible-light photoredox catalysis
title Arylcarboxylation of unactivated alkenes with CO(2) via visible-light photoredox catalysis
title_full Arylcarboxylation of unactivated alkenes with CO(2) via visible-light photoredox catalysis
title_fullStr Arylcarboxylation of unactivated alkenes with CO(2) via visible-light photoredox catalysis
title_full_unstemmed Arylcarboxylation of unactivated alkenes with CO(2) via visible-light photoredox catalysis
title_short Arylcarboxylation of unactivated alkenes with CO(2) via visible-light photoredox catalysis
title_sort arylcarboxylation of unactivated alkenes with co(2) via visible-light photoredox catalysis
topic Article
url 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
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