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The synthetic utility of NaN 3 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 CH 3 CN, 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 N 1-arylation of benzotriazole is also presented.

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