Understanding the fate of the Banert cascade of propargylic azides. Sigmatropic versus prototropic pathway

DI GRESIA, GABRIEL ; VILLAREAL PARRA, MIGUEL; LABADIE, GUILLERMO R.; VALLEJOS, MARGARITA M.

Conferencia; LatinXChem Twitter Conference 2021; 2021

The Banert cascade is an efficient synthetic strategy for obtaining 4,5-disubstituted 1,2,3-triazoles. Such cascade can proceed by either sigmatropic or prototropic mechanism depending on the substrates and conditions. In this work the mechanisms of both pathways from propargylic azides with different electronic features were investigated using DFT and QTAIM approach, and the results were consistent with the experimental data. We found a clear relationship between the electrophilicity index of propargylic azides and the energy barriers for both pathways