Copper(II)-Catalyzed Oxidative Cross-Coupling of Anilines, Primary Alkyl Amines, and Sodium Azide Using TBHP: A Route to 2-Substituted Benzimidazoles

Devulapally Mahesh, Pradeep Sadhu and Tharmalingam Punniyamurthy*

*Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India, Email: tpunniiitg.ernet.in

D. Mahesh, P. Sadhu, T. Punniyamurthy, J. Org. Chem., 2016, 81, 3227-3234.

DOI: 10.1021/acs.joc.6b00186

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Abstract

A copper(II)-catalyzed oxidative cross-coupling of anilines, primary alkyl amines, and sodium azide provides benzimidazoles in the presence of TBHP at moderate temperature via a domino C-H functionalization, transimination, ortho-selective amination, and a cyclization sequence. The reaction offers broad substrate scope and functional group compatibility.

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proposed reaction pathway

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Copper(I)-Catalyzed Regioselective Amination of N-Aryl Imines Using TMSN₃ and TBHP: A Route to Substituted Benzimidazoles

D. Mahesh, P. Sadhu, T. Punniyamurthy, J. Org. Chem., 2015, 80, 1644-1650.

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Key Words

benzimidazoles, TBHP, multicomponent reactions

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ID: J42-Y2016