P
cross-coupling
cyclization
nitrogen heterocycles
organocatalysis
phosphorus
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
09 03 2020
09 03 2020
Historique:
received:
20
11
2019
revised:
12
12
2019
pubmed:
24
12
2019
medline:
18
3
2021
entrez:
24
12
2019
Statut:
ppublish
Résumé
An organocatalytic method for the modular synthesis of diverse N-aryl and N-alkyl azaheterocycles (indoles, oxindoles, benzimidazoles, and quinoxalinediones) is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) and a hydrosilane reductant to drive the conversion of ortho-functionalized nitroarenes into azaheterocycles through sequential intermolecular reductive C-N cross coupling with boronic acids, followed by intramolecular cyclization. This method enables the rapid construction of azaheterocycles from readily available building blocks, including a regiospecific approach to N-substituted benzimidazoles and quinoxalinediones.
Identifiants
pubmed: 31869510
doi: 10.1002/anie.201914851
pmc: PMC7054160
mid: NIHMS1066025
doi:
Substances chimiques
Benzimidazoles
0
Boronic Acids
0
Organophosphorus Compounds
0
Quinoxalines
0
Silanes
0
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Langues
eng
Sous-ensembles de citation
IM
Pagination
4505-4510Subventions
Organisme : NIGMS NIH HHS
ID : R01 GM114547
Pays : United States
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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