Internal redox amidation of ¦Á,¦Â-unsaturated aldehydes in ionic liquids. The electrochemical route

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• 作者：Marta Feroci^a ; ^{marta.feroci@uniroma1.it} ; Isabella Chiarotto^a ; ^{isabella.chiarotto@uniroma1.it} ; Achille Inesi^b ; ^{achille.inesi@uniroma1.it}
• 关键词：Amides ; N-Heterocyclic carbenes ; ¦Á ; ¦Â-Unsaturated aldehydes ; Room temperature ionic liquids ; Organic electrosynthesis
• 刊名：Electrochimica Acta
• 出版年：2013
• 出版时间：1 February, 2013
• 年：2013
• 卷：89
• 期：Complete
• 页码：692-699
• 全文大小：2435 K

文摘

A simple, N-heterocyclic carbene (NHC) activated synthesis of amides has been performed via electrolysis, carried out under galvanostatic control, of an ionic liquid (Bmim-BF₄) followed by addition to the catholyte of an ¦Á,¦Â-unsaturated aldehyde and amine. Amides have been isolated, in good to elevated yields, in the absence of any base, co-catalyst and organic solvent. The selectivity of amidation, versus the formation of imine as by-product, has been related to the molar ratio electrogenerated NHC/aldehyde. The results, obtained using ionic liquids and electrochemical procedures, have been compared with those obtained using organic solvents and classical procedures.