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

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.

Visible Light-Induced Hydroacylation of Benzylidenemalononitriles with Aroyl Chlorides Using Silane as a Hydrogen Donor

“…The emergence of photochemistry has led to the development of greener and more functional group-tolerant hydroacylation methods, improving regio- and chemoselectivity. Additionally, it has expanded the exploration of alternative acyl sources, such as aroyl chlorides, benzoic acids, , etc.…”

“…Acyl radicals play a crucial role in building different valuable carbonyl compounds . Typically, acyl radicals can be generated from aldehydes, , anhydrides, α-keto acids, or benzoic acids , through photocatalysis or with the use of additive agents. Furthermore, the use of acyl chlorides, through direct oxidative quenching of photocatalysts, provides a supplementary method for obtaining acyl radicals.…”