Generation of Trityl Cation Derivatives from Triarylmethyl Azides for C–F Azidation of o -Hydrosilyl-Substituted Benzotrifluorides

In this study, the equilibrium formation of trityl cations from trityl azide derivatives was examined under various conditions. The generation of trityl cations was promoted by the presence of 1,1,1,3,3,3-hexafluoro-2-propanol, electron-donating substituents on trityl azide derivatives, and Lewis acids. The equilibrium generation of trityl cations allowed the C–F azidation of o-hydrosilyl-substituted benzotrifluorides. Further transformations of the resulting azido and fluorosilyl moieties enabled the facile preparation of a wide variety of fluorine-containing triazoles.