Controlled Oxygenation of Multiple Contiguous C–H Bonds via Electrophotocatalysis

Abstract

Chemical reactions that directly convert carbon-hydrogen (C–H) bonds to carbon-oxygen (C–O) bonds provide a powerful means to rapidly synthesize valuable organic compounds. However, achieving multiple C–H bond oxygenation reactions at the same time is challenging, particularly because of the risk of overoxidation. Here, we report the selective oxygenation of two or three contiguous C–H bonds, enabling the conversion of simple alkylarenes to diols, triols, or their corresponding acetates. The reactions are achieved using electrophotocatalysis—a process that utilizes both light and electricity to activate a single catalyst—to promote the oxidation reactions. The rapid increase in molecular complexity achieved by these multiple oxygenations enables the synthesis of some compounds of pharmaceutical interest by dramatically shorter sequences than previously achieved.