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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.