Electricity-driven reductive coupling reaction of imines with N-(acyloxy)phthalimides

Abstract

The reductive coupling reaction between imines and N-(acyloxy)phthalimides (NHPI esters) under electrochemical conditions has been developed. The reaction system was mild and easy to operate without the involvement of metals, and the imines could be generated from aldehydes and amines in situ. 4-Fluorobenzoic acid and N,N-diisopropylethanamine (DIPEA) could both improve the reaction efficiency, and the ion pair formed by these two reagents could avoid the use of electrolytes. The mechanism experiments verified the formation of alkyl radical intermediates, and combined with the results of cyclic voltammetry experiments, it was judged that the reaction underwent the process of radical addition.