Divergent C−H Amidations and Imidations by Tuning Electrochemical Reaction Potentials

Abstract

Electrochemical C-H functionalizations are attractive transformations, as they are capable of avoiding the use of transition metals, pre-oxidized precursors, or suprastoichiometric amounts of terminal oxidants. Herein an electrochemically tunable method was developed that enabled the divergent formation of cyclic amines or imines by applying different reaction potentials. Detailed cyclic voltammetry analyses, coupled with chronopotentiometry experiments, were carried out to provide insight into the mechanism, while atom economy was assessed through a paired electrolysis. Selective C-H amidations and imidations were achieved to afford five- to seven-membered sulfonamide motifs that could be employed for late-stage modifications.