Photoredox Catalysis-Enabled C–H Difluoromethylation of Heteroarenes with Pentacoordinate Phosphorane as the Reagent

Abstract

Difluoromethylated heterocyclic compounds have found broad applications in numerous bioactive molecules. Herein, we report photoredox catalysis-induced direct C-H difluoromethylation of heterocycles by using bis(difluoromethyl) pentacoordinate phosphorane (PPh₃(CF₂H)₂, <b>1</b>) as the reagent. A variety of heterocycles, such as quinoxalin-2(1<i>H</i>)-one, thiophene, indole, and coumarin, are readily tailored with a difluoromethyl group. The method is featured as transition-metal-free by using an organic compound Erythrosin B as the catalyst and O₂ as the oxidant.