Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives

Herein, we report a protocol for the anaerobic oxidation of alcohols, amines, aldehydes, and imines promoted by photoexcited nitroarenes. Mechanistic studies support that photoexcited nitroarenes undergo double hydrogen atom transfer (HAT) steps with alcohols and amines to provide respective ketone and imine products. However, in the presence of aldehydes and imines, a successive HAT and oxygen atom transfer (OAT) event occurs to yield carboxylic acids and amides, respectively. This transformation is amenable to a continuous-flow photochemical setup, which led to significantly reduced reaction times.