Selective Synthesis of N-H and N-Aryl Benzotriazoles by the 3+2] Annulation of Sodium Azide with Arynes

Guin, Avishek and Gaykar, Rahul N and Bhattacharjee, Subrata and Biju, Akkattu T (2019) Selective Synthesis of N-H and N-Aryl Benzotriazoles by the 3+2] Annulation of Sodium Azide with Arynes. In: JOURNAL OF ORGANIC CHEMISTRY, 84 (19). pp. 12692-12699.

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Abstract

The synthetic utility of NaN3 as the azide component in the 3 + 2] annulation with arynes generated from 2-(trimethylsilyl)aryltriflates resulting in the transition-metal-free synthesis of N-H and N-aryl benzotriazoles has been demonstrated. Using CsF as the fluoride source in CH3CN, the N-H benzotriazoles are formed in high selectivity instead of the expected azidobenzene. Interestingly, N-aryl benzotriazoles are formed using KF and THF as solvent in an open-flask reaction. Moreover, a method for the N1-arylation of benzotriazole is also presented.

Item Type:	Journal Article
Publication:	JOURNAL OF ORGANIC CHEMISTRY
Publisher:	AMER CHEMICAL SOC
Additional Information:	Copyright of this article belongs to AMER CHEMICAL SOC
Keywords:	TRANSITION-METAL-FREE; BENZYNE-CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITION; NITRILE OXIDES; EMPLOYING ARYNES; ACTIVATION; AMINATION; ARYLATION; BIARYLS; ALKYNES
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	28 Nov 2019 11:36
Last Modified:	28 Nov 2019 11:36
URI:	http://eprints.iisc.ac.in/id/eprint/63837

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