Organic Chemistry Portal

Abstracts

Search:

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

An-Jing Wang, Chun-Yan She, Yu-Die Zhang, Li-Han Zhao, Wen-Ming Shu* and Wei-Chu Yu*

*College of Chemistry and Environmental Engineering, Yangtze University, Jingzhou 434023, P. R. China, Email: shuwmyangtzeu.edu.cn, yuweichu126.com

A.-J. Wang, C.-Y. She, Y.-D. Zhang, L.-H. Zhao, W.-M. Shu, W.-C. Yu, J. Org. Chem., 2022, 87, 16099-16105.

DOI: 10.1021/acs.joc.2c01814


see article for more reactions

Abstract

A copper(II)-promoted denitrogenation/oxidation reaction of α-azido ketones and TEMPO as an oxidant provides primary α-ketoamides. α-Azido ketones were denitrogenated in situ to form an imino ketone intermediate, which underwent a radical addition process and radical migration to form α-ketoamides.

see article for more examples


proposed mechanism



Key Words

oxidation, TEMPO


ID: J42-Y2022