Reactivity of Electrogenerated Imidazole-2-Ylidene in Ionic Liquids: Synthetic Implications

The cathodic reduction of an imidazolium ionic liquid, under galvanostatic conditions, leads to the formation of the corresponding carbene, imidazole-2-ylidene, and molecular hydrogen. This carbene can behave as a base and/or as a nucleophile, depending on the reaction partner. In particular, we have studied the reactivity of this N-heterocyclic carbene in alkylation and acylation reactions, in the synthesis of β-lactams, in the Henry reaction, in the synthesis of thiones and in the benzoin condensation. ©The Electrochemical Society