Photocatalytic organosulfur reagent-promoted selective mono-(deutero)hydrodechlorination

Abstract

Selective partial C–Cl bond reduction represents an important strategy for the construction of valuable chlorine-containing skeletons. Herein, we report an efficient and straightforward mono-(deutero)hydrodechlorination strategy of various trichloroacetyl esters and amides for the incorporation of gem-dichloromethyl moieties. The proposed mechanism involves key electron donor–acceptor (EDA) complexes formed between catalytic cyclohexanethiol (CySH) and substrates, which undergo single-electron transfer (SET) processes under blue light irradiation to provide the gem-dichloro radical anion and CyS˙. A gram-scale reaction and late-stage modification of bioactive molecules further demonstrate the potential utility of this methodology.