Arylcarboxylation of unactivated alkenes with CO2 via visible-light photoredox catalysis
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-ca...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2023-06-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-023-39240-8 |
| _version_ | 1797801376796901376 |
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| author | Wei Zhang Zhen Chen Yuan-Xu Jiang Li-Li Liao Wei Wang Jian-Heng Ye Da-Gang Yu |
| author_facet | Wei Zhang Zhen Chen Yuan-Xu Jiang Li-Li Liao Wei Wang Jian-Heng Ye Da-Gang Yu |
| author_sort | Wei Zhang |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-13T04:49:32Z |
| format | Article |
| id | doaj.art-7342db3cd57d4148aae36aaf4a6bda48 |
| institution | Directory Open Access Journal |
| issn | 2041-1723 |
| language | English |
| last_indexed | 2024-03-13T04:49:32Z |
| publishDate | 2023-06-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj.art-7342db3cd57d4148aae36aaf4a6bda482023-06-18T11:18:40ZengNature PortfolioNature Communications2041-17232023-06-0114111010.1038/s41467-023-39240-8Arylcarboxylation of unactivated alkenes with CO2 via visible-light photoredox catalysisWei Zhang0Zhen Chen1Yuan-Xu Jiang2Li-Li Liao3Wei Wang4Jian-Heng Ye5Da-Gang Yu6Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan UniversityKey Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan UniversityKey Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan UniversitySchool of Chemistry and Chemical Engineering, Chongqing UniversityKey Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan UniversityKey Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan UniversityKey Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan UniversityAbstract 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.https://doi.org/10.1038/s41467-023-39240-8 |
| spellingShingle | Wei Zhang Zhen Chen Yuan-Xu Jiang Li-Li Liao Wei Wang Jian-Heng Ye Da-Gang Yu Arylcarboxylation of unactivated alkenes with CO2 via visible-light photoredox catalysis Nature Communications |
| title | Arylcarboxylation of unactivated alkenes with CO2 via visible-light photoredox catalysis |
| title_full | Arylcarboxylation of unactivated alkenes with CO2 via visible-light photoredox catalysis |
| title_fullStr | Arylcarboxylation of unactivated alkenes with CO2 via visible-light photoredox catalysis |
| title_full_unstemmed | Arylcarboxylation of unactivated alkenes with CO2 via visible-light photoredox catalysis |
| title_short | Arylcarboxylation of unactivated alkenes with CO2 via visible-light photoredox catalysis |
| title_sort | arylcarboxylation of unactivated alkenes with co2 via visible light photoredox catalysis |
| url | https://doi.org/10.1038/s41467-023-39240-8 |
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