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.
Reactivity of electrogenerated imidazole-2-ylidenes in ionic liquids: synthetic implications / Feroci, Marta; Chiarotto, Isabella; Monica, Orsini; Giovanni, Sotgiu; Inesi, Achille. - In: ECS TRANSACTIONS. - ISSN 1938-5862. - ELETTRONICO. - 25:18(2010), pp. 1-11. (Intervento presentato al convegno Symposium on Synthetic and Mechanistic Organic Electron Transfer Reactions held during the 216th Meeting of the Electrochemical-Society (ECS) tenutosi a Vienna; Austria nel OCT 04-09, 2009) [10.1149/1.3312759].
Reactivity of electrogenerated imidazole-2-ylidenes in ionic liquids: synthetic implications
FEROCI, Marta;CHIAROTTO, Isabella;INESI, ACHILLE
2010
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
