Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 23, Pages 16099-16105Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01814
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Funding
- National Natural Science Foundation of China
- CNPC Innovation Fund
- [21801022]
- [2021DQ02-0203]
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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.
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.
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