An oxidative coupling of amines to give imines in ionic liquids (ILs) under metal-free aerobic conditions has been developed. The high efficiency achievable in ILs is mechanistically explained in terms of activation of the starting materials (benzylamine and molecular oxygen) by an initial electron transfer, promoted by the ionic nature of the solvent. Reactivity data of variously p-substituted benzylamines show a general deactivating effect, which would imply a change in the rate-determining step in the reaction mechanism.

Ionic-Liquid-Assisted Metal-Free Oxidative Coupling of Amines To Give Imines / Monopoli, Antonio; Cotugno, Pietro; Iannone, Francesco; Ciminale, Francesco; Dell'Anna, Maria Michela; Mastrorilli, Pietro; Nacci, Angelo. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 27(2014), pp. 5925-5931. [10.1002/ejoc.201402530]

Ionic-Liquid-Assisted Metal-Free Oxidative Coupling of Amines To Give Imines

Maria Michela Dell'Anna;Piero Mastrorilli;
2014-01-01

Abstract

An oxidative coupling of amines to give imines in ionic liquids (ILs) under metal-free aerobic conditions has been developed. The high efficiency achievable in ILs is mechanistically explained in terms of activation of the starting materials (benzylamine and molecular oxygen) by an initial electron transfer, promoted by the ionic nature of the solvent. Reactivity data of variously p-substituted benzylamines show a general deactivating effect, which would imply a change in the rate-determining step in the reaction mechanism.
2014
Ionic-Liquid-Assisted Metal-Free Oxidative Coupling of Amines To Give Imines / Monopoli, Antonio; Cotugno, Pietro; Iannone, Francesco; Ciminale, Francesco; Dell'Anna, Maria Michela; Mastrorilli, Pietro; Nacci, Angelo. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 27(2014), pp. 5925-5931. [10.1002/ejoc.201402530]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11589/811
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