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Arylcarboxylation of unactivated alkenes with CO2 via visible-light photoredox catalysis
Nature Communications ( IF 14.7 ) Pub Date : 2023-06-14 , DOI: 10.1038/s41467-023-39240-8
Wei Zhang 1, 2 , Zhen Chen 1 , Yuan-Xu Jiang 1 , Li-Li Liao 3 , Wei Wang 1 , Jian-Heng Ye 1 , Da-Gang Yu 1, 4
Affiliation  

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.



中文翻译:

通过可见光光氧化还原催化未活化烯烃与 CO2 的芳基羧化

烯烃与 CO 2的光催化羧化是合成高附加值羧酸的有前途且可持续的策略。然而,由于其低反应性,它具有挑战性并且很少研究未活化的烯烃。在此,我们报告了未活化烯烃与 CO 2的可见光光氧化还原催化芳基羧化反应, 提供各种 tetrahydronaphthalen-1-ylacetic acids, indan-1-ylacetic acids, indolin-3-ylacetic acids, chroman-4-ylacetic acids 和 thiochroman-4-ylacetic acids,产量适中。该反应具有化学选择性和区域选择性高、反应条件温和(1个大气压、室温)、底物适用范围广、官能团相容性好、产品易于扩展和衍生化等特点。机理研究表明,二氧化碳自由基阴离子的原位生成以及随后对未活化烯烃的自由基加成可能参与该过程。

更新日期:2023-06-15
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