Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent.

Abstract

The carboamination of unsaturated molecules using bifunctional reagents is considered an attractive approach for the synthesis of nitrogen-containing compounds. However, bifunctional C-N reagents have never been employed in the carboamination of cyclopropane. In this study, we use an N-heterocyclic carbene (NHC), N-benzoyl saccharin, as a bifunctional reagent and a photoredox catalyst for a dual-catalyzed 1,3-aminoacylation of cyclopropane. NHCs play multiple roles, functioning as Lewis base catalysts to activate C-N bonds, promoting the oxidative quenching process of PC*, and acting as efficient acyl radical transfer catalysts for the formation of C-C bonds. The oxidative quenching process between the excited-state PC* and acyl NHC adduct is the key to the photooxidation generality of aryl cyclopropanes.