Triazabicyclodecene as an Organocatalyst for the Regiospecific Synthesis of 1,4,5-Trisubstituted N-Vinyl-1,2,3-triazoles

Abstract

Herein we report on the 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) catalyzed enolate-mediated regiospecific synthesis of 1,4,5-trisubstituted N-vinyl-1,2,3-triazoles from simple activated carbonyl compounds and N-vinyl azides through [3+2] cycloaddition; upon further hydrogenation, 1,4,5-trisubstituted N-alkyl-1,2,3-triazoles are furnished. Both the organo-click and hydrogenation reactions proceeded in excellent yields with high rates and selectivities at 25 °C within a few hours.