Electrochemical dibromoacetoxylation and trihalogenation of allylarenes

Abstract

Trifunctionalization serves as an efficient method for rapidly enhancing molecular complexity by incorporating three functional groups from simple, readily available raw materials. Herein, we describe an electrochemical trifunctionalization protocol for allylarenes that enables the synthesis of a diverse range of dibromoacetoxylated and trihalogenated products. Further gram-scale synthesis and divergent transformation of products demonstrate potential application in the pharmaceutical industry. Mechanistic studies reveal the process involves a cascade oxidative difunctionalization of CC bond and oxidative functionalization of benzylic C–H bond.