Copper/TEMPO-Promoted Denitrogenation/Oxidation Reaction for Synthesis of Primary α-Ketoamides Using α-Azido Ketones

A copper(II)-promoted denitrogenation/oxidation reaction for the preparation of primary alpha-ketoamides was developed using alpha-azido ketones as a substrate and TEMPO as an oxidant. alpha-Azido ketones were denitrogenated in situ to form an imino ketone intermediate, which underwent a radical addition process and radical migration to form alpha- ketoamides. It is worth noting that the imino ketone intermediate is the key to this reaction.

Automated summary

A copper(II)-promoted denitrogenation/oxidation reaction was developed to prepare primary alpha-ketoamides using alpha-azido ketones as substrate and TEMPO as oxidant. In this reaction, alpha-azido ketones were denitrogenated in situ to form an imino ketone intermediate, which then underwent radical addition and radical migration to yield alpha-ketoamides. The imino ketone intermediate plays a crucial role in this reaction.