Visible-light photoredox-catalyzed umpolung carboxylation of carbonyl compounds with CO2

Guang-Mei Cao, Xin-Long Hu, Li-Li Liao, Si-Shun Yan, Lei Song, Jason J. Chruma, Li Gong and Da-Gang Yu ()
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Guang-Mei Cao: Sichuan University
Xin-Long Hu: Sichuan University
Li-Li Liao: Sichuan University
Si-Shun Yan: Sichuan University
Lei Song: Sichuan University
Jason J. Chruma: Sichuan University
Li Gong: Sichuan University
Da-Gang Yu: Sichuan University

Nature Communications, 2021, vol. 12, issue 1, 1-10

Abstract: Abstract Photoredox-mediated umpolung strategy provides an alternative pattern for functionalization of carbonyl compounds. However, general approaches towards carboxylation of carbonyl compounds with CO2 remain scarce. Herein, we report a strategy for visible-light photoredox-catalyzed umpolung carboxylation of diverse carbonyl compounds with CO2 by using Lewis acidic chlorosilanes as activating/protecting groups. This strategy is general and practical to generate valuable α-hydroxycarboxylic acids. It works well for challenging alkyl aryl ketones and aryl aldehydes, as well as for α-ketoamides and α-ketoesters, the latter two of which have never been successfully applied in umpolung carboxylations with CO2 (to the best of our knowledge). This reaction features high selectivity, broad substrate scope, good functional group tolerance, mild reaction conditions and facile derivations of products to bioactive compounds, including oxypheonium, mepenzolate bromide, benactyzine, and tiotropium. Moreover, the formation of carbon radicals and carbanions as well as the key role of chlorosilanes are supported by control experiments.

Date: 2021
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DOI: 10.1038/s41467-021-23447-8

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