Guin, Avishek ; Gaykar, Rahul N. ; Bhattacharjee, Subrata ; Biju, Akkattu T. (2019) Selective Synthesis ofN-H andN-Aryl Benzotriazoles by the [3 + 2] Annulation of Sodium Azide with Arynes The Journal of Organic Chemistry, 84 (19). pp. 12692-12699. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/acs.joc.9b02198
Related URL: http://dx.doi.org/10.1021/acs.joc.9b02198
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: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society |
| ID Code: | 128604 |
| Deposited On: | 03 Nov 2022 06:45 |
| Last Modified: | 03 Nov 2022 06:45 |
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