On Water Metal-Catalyst-Free Oxidative Coupling-Amidation of Amines to Access Imines and Amides

Abstract

A simple route toward the selective synthesis of imines and amides through oxidative coupling-oxidative amidation of amines using widely available NaOCl is presented. Under this approach, unprecedented one-pot synthesis of symmetrical and unsymmetrical secondary amides from primary amines as a single starting material is reported. This metal-catalyst-free protocol relies upon "on water" acceleration to obtain the desired products in high yields. An additive-based robustness screen was conducted to demonstrate the high reaction tolerance to several chemical motifs. Furthermore, mechanistic studies support a proposed pathway for the targeted oxidation products.