Oxidative N-N Bond Formation Versus the Curtius Rearrangement.
Benzamide
Cross dehydrogenative coupling
Curtius Rearrangement
Oxidative N─N bond formation
PIDA
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
04 Jul 2024
04 Jul 2024
Historique:
revised:
03
07
2024
received:
19
06
2024
accepted:
04
07
2024
medline:
4
7
2024
pubmed:
4
7
2024
entrez:
4
7
2024
Statut:
aheadofprint
Résumé
The oxidative formation of N-N bonds from primary amides has been recently reported and then retracted in the journal Nature Communications by Kathiravan, Nicholls, and coauthors, utilizing a hypervalent iodane reagent. Unfortunately, the authors failed to recognize the Curtius reaction taking place under the described reaction conditions. Thus, the claimed N-N coupling products were not formed. Instead, the Curtius rearrangement urea coupling products were obtained. We demonstrate this herein by means of NMR and x-ray analysis, as well as with the support of an alternative synthetic route.
Identifiants
pubmed: 38963800
doi: 10.1002/chem.202402355
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202402355Informations de copyright
© 2024 Wiley‐VCH GmbH.