Visible-Light-Induced Acylative Coupling of Benzoic Acid Derivatives with Alkenes to Dihydrochalcones

Org Lett. 2022 Oct 14;24(40):7271-7275. doi: 10.1021/acs.orglett.2c02538. Epub 2022 Oct 3.

Abstract

A strategy was developed for the visible-light-induced photocatalytic synthesis of dihydrochalcone via the deoxygenation and coupling of benzoic acid derivatives with alkenes using diphenyl sulfide as the O-transfer reagent. Under mild photoredox conditions, a series of dihydrochalcone derivatives were produced in moderate to good yields. A mechanism for the visible-light-induced free-radical coupling was proposed on the basis of the control experiments. The protocol provides a new strategy the generation of acyl radicals from carboxylic acids and the synthesis of dihydrochalcones.