Synthesis of α-ketoamides oxidative amidation of diazo compounds with -benzoyl hydroxylamines as nitrogen source and the oxidant

A simple, efficient method has been described for the construction of an array of α-ketoamides from readily available O -benzoyl hydroxylamines and diazo compounds as starting materials. There was a combined use of CuI as a catalyst and H 2 O as the oxygen source. The investigation reveals that the...

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Veröffentlicht in:Organic & biomolecular chemistry 2024-08, Vol.22 (33), p.678-6712
Hauptverfasser: Chen, Wenwen, Zhang, Xinyin, Wang, Xinyu, Zhang, EnXuan, Wang, Zu-Li, Jia, Jianfeng
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Zusammenfassung:A simple, efficient method has been described for the construction of an array of α-ketoamides from readily available O -benzoyl hydroxylamines and diazo compounds as starting materials. There was a combined use of CuI as a catalyst and H 2 O as the oxygen source. The investigation reveals that the O -benzoyl hydroxylamines serve a dual role as both an amine source and the oxidant in this mechanism, thereby obviating the need for additional oxidants in the transformation process. This methodology could give a wider range of products in good to excellent yields for most substrates, and thus, we provide a new idea for the synthesis of α-ketoamides. An efficient method for the construction of an array of α-ketoamides has been described from readily available O -benzoyl hydroxylamines and diazo compounds as starting materials by the combined use of CuI as a catalyst and H 2 O as oxygen source.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00883a