Visible-Light Induced Iron-Catalyzed Hydroxymethylation of N-Heterocycles

A new strategy for iron-catalyzed visible-light induced hydroxymethylation of N-heterocycles with methanol under mild conditions was developed. By employing FeCl3 as the catalyst, 2-methylisonicotinic acid as the ligand, TsOH as the acid, air as the oxidant, and aqueous MeOH as the solvent, varieties of substituted quinolines, isoquinolines, pyridines, benzothiazole and voriconazole were hydroxymethylated smoothly in good to excellent yields, exhibiting good substrate scope. This strategy features green reaction conditions, excellent atom-economy and simple operations. It has potential applicable value in late-stage structure modification of drug molecule.