On the reactivity and stability of electrogenerated N-heterocyclic carbene in parent 1-butyl-3-methyl-1H-imidazolium tetrafluoroborate: Formation and use of N-heterocyclic carbene-CO₂ adduct as latent catalyst

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• 作者：Marta Feroci ; Isabella Chiarotto ; Stefano Vecchio Ciprioti ; Achille Inesi
• 关键词：N-heterocyclic carbene ; NHC-CO2 adduct ; Cyclic voltammetry ; Cathodic reduction ; Carbon dioxide
• 刊名：Electrochimica Acta
• 出版年：30 October, 2013
• 年：2013
• 卷：109
• 期：Complete
• 页码：95-101
• 全文大小：1018 K

文摘

A simple electrolysis (under galvanostatic conditions) of the room temperature ionic liquid 1-butyl-3-methyl-1m>Hm>-imidazolium tetrafluoroborate, BMIm-BF₄, yields, after bubbling CO₂ into the catholyte, the adduct NHC-CO₂. The considerable stability of this NHC-CO₂ adduct, at room temperature, in the parent ionic liquid as solvent, has been compared with the one of free NHC in the same BMIm-BF₄. The BMIm-BF₄ solution containing NHC-CO₂ adduct, suitably triggered (US irradiation or 120 掳C), is able to release free NHC. The NHC-CO₂ adduct usefulness has been demonstrated using it as efficient latent catalyst, in BMIm-BF₄ as solvent, in the benzoin condensation and in the oxidative esterification of cinnamaldehyde with benzyl alcohol.