A One‐Pot Copper‐Catalyzed 3‐Fold C–N Bond Coupling Strategy to the Synthesis of Substituted Benzimidazoles. Issue 44 (5th June 2020)

• Record Type: Journal Article
• Authors: Subramanian, Parthasarathi; Kaliappan, Krishna P.
• Other Names: Datta Anindya guestEditor.
• Is Part Of: European journal of organic chemistry. Issue 44(2020)
• Page Start: 6915
• Page End: 6921
• Publication Date: 2020-06-05
• Subjects: Copper catalysis -- One‐pot -- C–H activation -- Heterocycles -- C–N coupling; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000428
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : An efficient, one‐pot copper catalyzed 3‐fold C–N bond‐coupling strategy leading to pharmaceutically relevant benzimidazole heterocycles is reported. Our strategy involves a copper catalyzed intramolecular C–N coupling of N, N' ‐bis(2‐bromophenyl)formamidine to provide 1‐(2‐bromophenyl)‐1H‐benzimidazole which upon intermolecular coupling with 2‐amino pyridines and a cascade sp 2 C–H amination furnished a range of benzimidazo[1, 2‐ a ]benzimidazoles. Abstract : One‐pot reaction leading to direct access to biologically relevant heterocycles is highly recommended in chemical synthesis. One such standout method, manifold C–N bond formations route to the synthesis of benzimidazo[1, 2‐ a ]benzimidazoles, is described. Our methodology involves a copper catalyzed intramolecular C–N coupling of N, N' ‐bis(2‐bromophenyl)formimidamide to provide 1‐(2‐bromophenyl)‐1H‐benzimidazole which upon intermolecular coupling with 2‐amino pyridines and a cascade sp 2 C–H amination provided a range of benzimidazo[1, 2‐ a ]benzimidazoles.