Transition Metal- and Base-Free Electrochemical aza-Michael Addition of Aromatic aza-Heterocycles or Ts-Protected Amines to α,β-Unsaturated Alkenes Mediated by NaI

Abstract

A highly efficient and mild electrochemical protocol has been developed for the aza-Michael addition of aromatic aza-heterocycles or Ts-protected amines with α,β-unsaturated alkenes to give corresponding β-amino sulfone, β-amino nitrile, β-amino ester, and β-amino ketone in moderate to excellent yields. The chemistry proceeded using NaI as a redox mediator in an undivided cell at ambient temperature. Unlike the conventional aza-Michael additions, the utilization of strong acid, base, or transition metal-based catalysts is circumvented. In addition, it was observed the electrochemically in-situ-generated molecular iodine has higher activity than that under nonelectrochemical reaction conditions.