Organic Chemistry Portal

Abstracts

Search:

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)



see article for more reactions

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.

see article for more examples

proposed reaction pathway



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.


Key Words

benzimidazoles, TBHP, multicomponent reactions


ID: J42-Y2016