The Parasram Lab reported the use of photoexcited nitroarenes for the anaerobic oxidation of C(sp2)–H and C(sp3)–H heteroatom systems, which can provide access to synthetically useful carbonyl and imine derivatives. The work, entitled “Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives” was published in Organic Letters. The contributing authors include co-first authors Joshua K. Mitchell and Dr. Waseem Hussain, co-second authors Dr. Ajay Bansode and Ryan O’Connor, Dr. Dan Wise, Michael Choe, and Principal Investigator Assistant Professor Marvin Parasram. Click here to read the full article in ORGANIC LETTERS.
Abstract: 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.