Palladium-Catalyzed Synthesis of 2-Aryl-2H-Benzotriazoles from Azoarenes and TMSN3

Nilufa Khatun; Anju Modi; Wajid Ali; Bhisma K Patel

doi:10.1021/acs.joc.5b01706

Palladium-Catalyzed Synthesis of 2-Aryl-2H-Benzotriazoles from Azoarenes and TMSN3

J Org Chem. 2015 Oct 2;80(19):9662-70. doi: 10.1021/acs.joc.5b01706.

Authors

Nilufa Khatun¹, Anju Modi¹, Wajid Ali¹, Bhisma K Patel¹

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Guwahati , North Guwahati 781 039, India.

PMID: 26372371
DOI: 10.1021/acs.joc.5b01706

Abstract

Substrate-directed ortho C-H amination of azoarenes using TMSN3 as the source of nitrogen leading to the synthesis of 2-aryl-2H-benzotriazoles has been accomplished with the help of Pd/TBHP combinations. An intermolecular o-azidation (C-N bond formation) followed by an intramolecular N-N bond formation via nucleophilic attack of one of the azo nitrogen onto the o-azide nitrogen leads to cyclization with the expulsion of N2.