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 (free Supporting Information)
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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
D. Mahesh, P. Sadhu, T. Punniyamurthy, J. Org. Chem., 2015, 80, 1644-1650.