Unveiling the High Reactivity of Esters Bearing a Cationic Substituent at the Carbonyl Carbon

The effect of a cationic heterocyclic ring on the reactivity of an adjacent functional group has not been extensively studied thus far. Herein, we disclosed the unprecedented high electrophilicity of the carbonyl carbon attached to a cationic heterocycle. Control experiments and density functional theory calculations revealed that the cationic heterocycle moiety is responsible for the high reactivity. In addition, the findings of this work were used for the postmodification of metal triazolylidene complexes.