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Updated: Jan 5, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Cu-Mediated Amination of (Hetero)Aryl C-H bonds with NH Azaheterocycles
Jin-Feng Yu1, Jian-Jun Li1, Peng Wang1,2
1State key laboratory of organometallic chemistry, Center for excellence in molecular synthesis, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032, P. R. China.
Abstract:
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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