Arenethiolate-catalyzed Caryl–F bond activation: synthesis of oxindoles†

Abstract

Single-electron reduction of the C_aryl–F bond is quite challenging due to its high reduction potential. Herein, we report an arenethiolate-catalyzed single-electron reduction of the C_aryl–F bond to access oxindoles. A variety of oxindoles are provided in moderate to excellent yields through a single-electron reduction/cyclization/single-electron oxidation process. Furthermore, the 1,5-HAT of inert C–H could be achieved with this method. A plausible pathway with arenethiolate as a SET catalyst is proposed on the basis of mechanistic studies.