Atmospheric Oxygen Facilitated Oxidative Amidation to α-Ketoamides and Unusual One Carbon Degradative Amidation to N-Alkyl Amides

Abstract

A mild, transition-metal-free novel synthetic approach for the construction of C�O and C−N bonds has been demonstrated. Easily accessible gem-dibromoalkenes under similar conditions form oxidative amidation product α-ketoamides and unusual degradative amidation product N-alkyl amides by simply changing the amine substitute. Atmospheric air containing molecular oxygen proved to be an ideal oxidant for an amidation reaction. Under similar conditions, the electron-deficient gem-dibromoalkenes play a dual role with different formamides forming novel oxidative amidation products and by the state of art neighboring group participation of amine to unusual one-carbon degradative amidation products.

Electrochemical Formation of α-Ketoamides from Ketoximes through Non-Beckmann Mechanism Pathway

“…Accordingly, in recent decades, there has been considerable focus on advancing traditional methods for constructing α-ketoamide motifs in synthetic organic chemistry . Consequently, various efforts have been made to devise novel and convenient approaches for accessing α-ketoamides, employing a spectrum of catalysts, including metals, nonmetals, organocatalysts, photocatalysts, and electrocatalysts (Scheme B). − …”