Azolium and acetate ions in DMF: Formation of free N-heterocyclic carbene. A voltammetric analysis

Francesca D'Anna, Carla Rizzo, Achille Inesi, Luigi Ornano, Isabella Chiarotto, Marta Feroci

Risultato della ricerca: Article

3 Citazioni (Scopus)

Abstract

In order to reveal the possible formation of free N-heterocyclic carbene (NHC) in DMF-azolium and acetate solutions, the proton exchange equilibrium between azolium cations and CH3COO- was investigated (by cyclic voltammetry) by adding CH3COOH or tetrabutylammonium acetate to DMF solutions of imidazolium or thiazolium salts of different acidity.The voltammetric analysis confirms that the deprotonation of the azolium cation by CH3COO- (with the formation of free NHC) is significant in the case of the more acidic thiazolium cations, while it is not effective with the less acidic imidazolium ones.Accordingly, the NHC-catalyzed benzoin condensation was carried out in DMF solutions of azolium salts, tetrabutylammonium acetate, and benzaldehyde. Benzoin was isolated only starting from the more acidic thiazolium salts. (C) 2016 Elsevier B.V. All rights reserved.
Lingua originaleEnglish
pagine (da-a)55-58
Numero di pagine4
RivistaElectrochemistry Communications
Volume67
Stato di pubblicazionePublished - 2016

All Science Journal Classification (ASJC) codes

  • Electrochemistry

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