Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives
Joshua K. Mitchell, Waseem A. Hussain, Ajay H. Bansode, Ryan M. O’Connor, Dan E. Wise, Michael H. Choe, Marvin Parasram
Abstract
Herein, we report a protocol for the anaerobic oxidation of alcohols, amines, aldehydes, and imines promoted by photoexcited nitroarenes. Mechanistic studies support the idea that photoexcited nitroarenes undergo double hydrogen atom transfer (HAT) steps with alcohols and amines to provide the respective ketone and imine products. In the presence of aldehydes and imines, successive HAT and oxygen atom transfer (OAT) events occur to yield carboxylic acids and amides, respectively. This transformation is amenable to a continuous-photoflow setup, which led to reduced reaction times.
Topics & Concepts
ChemistryImineKetoneYield (engineering)Hydrogen atomCombinatorial chemistryOxygen atomAlcohol oxidationOrganic chemistryPhotochemistryAlcoholCatalysisMoleculeGroup (periodic table)MetallurgyMaterials scienceRadical Photochemical ReactionsOxidative Organic Chemistry ReactionsSynthesis and Catalytic Reactions