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 α-ketoamides was developed using α-azido ketones as a substrate and TEMPO as an oxidant. α-Azido ketones were denitrogenated in situ to form an imino ketone intermediate, which underwent a radical addition proce...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-12, Vol.87 (23), p.16099-16105
Main Authors: Wang, An-Jing, She, Chun-Yan, Zhang, Yu-Die, Zhao, Li-Han, Shu, Wen-Ming, Yu, Wei-Chu
Format: Article
Language:English
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Summary:A copper­(II)-promoted denitrogenation/oxidation reaction for the preparation of primary α-ketoamides was developed using α-azido ketones as a substrate and TEMPO as an oxidant. 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. It is worth noting that the imino ketone intermediate is the key to this reaction.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01814