Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 50, Pages 18141-18145Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910395
Keywords
azolation; C-H amination; copper; heterocycles; homogeneous catalysis
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Funding
- Shanghai Institute of Organic Chemistry, State Key Laboratory of Organometallic Chemistry
- Key Research Program of Frontier Science of the Chinese Academy of Sciences [QYZDJSSWSLH055]
- NSF under the CCI Center for Selective C-H Functionalization [CCHE-1700982]
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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.
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