Charge-Enhanced Reactivity of Esters by a Cationic Substituent

In this study, the high electrophilicity of carbonyl carbons attached to cationic heterocycles was observed. Triazolium-substituted esters underwent catalyst-free amidation with aliphatic amines at −50 °C and reduction with NaBH4 at −100 °C. The origin and generality of the high reactivity of these esters were systematically investigated. The findings of this work were utilized for the postmodification of N-heterocyclic carbenes, which are utilized as promising ligands in a wide range of transition-metal-catalyzed reactions.