Palladium-catalyzed synthesis of 2-Aryl-2H-benzotriazoles from azoarenes and TMSN3

Khatun, Nilufa ; Modi, Anju ; Ali, Wajid ; Patel, Bhisma K. (2015) Palladium-catalyzed synthesis of 2-Aryl-2H-benzotriazoles from azoarenes and TMSN3 The Journal of Organic Chemistry, 80 (19). pp. 9662-9670. ISSN 0022-3263

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Official URL: https://pubs.acs.org/doi/abs/10.1021/acs.joc.5b017...

Related URL: http://dx.doi.org/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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:113807
Deposited On:30 Apr 2018 12:18
Last Modified:30 Apr 2018 12:18

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