Cu‐Mediated Amination of (Hetero)Aryl C−H bonds with NH Azaheterocycles

Direct synthesis of N‐(hetero)arylated heteroarenes has been realized through Cu‐mediated C−N coupling of NH azaheterocycles with aryl C−H bonds under aerobic conditions. This method features a broad scope of both heterocyclic arenes (pyridine, quinoline, pyrazole, imidazole, furan, thiophene, benzo...

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Bibliographic Details
Published in:Angewandte Chemie 2019-12, Vol.131 (50), p.18309-18313
Main Authors: Yu, Jin‐Feng, Li, Jian‐Jun, Wang, Peng, Yu, Jin‐Quan
Format: Article
Language:English
Subjects:
Aerobic conditions
Amination
Angiotensin
Angiotensin II
Aromatic compounds
Azolierung
Benzimidazoles
Benzofuran
C-H-Aminierung
Carbazole
Carbazoles
Chemical synthesis
Chemistry
Heterocyclen
Homogene Katalyse
Imidazole
Indoles
Kupfer
Pyrazole
Pyridines
Quinoline
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Summary:Direct synthesis of N‐(hetero)arylated heteroarenes has been realized through Cu‐mediated C−N coupling of NH azaheterocycles with aryl C−H bonds under aerobic conditions. This method features a broad scope of both heterocyclic arenes (pyridine, quinoline, pyrazole, imidazole, furan, thiophene, benzofuran, and indole) and NH azaheterocycles (imidazole, pyrazole, indole, azindole, purine, indazole, benzimidazole, pyridone, carbazole), providing a versatile method for the synthesis of pharmaceutically important N‐(hetero)arylated heteroarenes. The versatility of this reaction was further demonstrated through late‐stage modification of marketed drugs and the synthesis of a key intermediate for accessing a class of angiotensin II receptor 1 antagonists. N‐(hetero)arylierte Heteroarene wurden durch Cu‐vermittelte C‐H‐Aminierung mit NH‐Azaheterocyclen synthetisiert. Diese durch die dirigierende Gruppe (DG) vermittelte Reaktion verläuft mit Luft als einzigem Oxidationsmittel. Die hervorragende Verträglichkeit mit Heterocyclen ermöglicht eine späte Diversifizierung einer breiten Palette von Arzneimitteln, die mehrere Heterocyclen enthalten.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201910395