Electrochemical One-Pot Diverse C(sp3)–X Bond (Including C–H, C–C, C–N, and C–O) Transformations and C(sp2)–H Acyloxylation of Alkylarenes

Abstract

In this study, an electrochemical one-pot cleavage of diverse C(sp3)–X bonds and acyloxylation of C(sp2)–H were reported. Based on the experimental results, we discovered for the first time that NH3 can strongly promote electrolyte dissolution and significantly increase the conductivity of a solution. Unlike previous C(sp2)–H acetoxylation reactions in which AcO– functions as a nucleophile, this reaction undergoes an acetoxy radical mechanism and prevents decarboxylation of the acetoxy radical. This reaction is advantageous because it is transition-metal-free, external-oxidant-free, atom- and step-economical, and applicable to diverse substrates; additionally, it uses mild reaction conditions and green and nontoxic solvents.