Ionic‐Liquid‐Assisted Metal‐Free Oxidative Coupling of Amines To Give Imines1. Issue 27 (15th August 2014)

• Record Type: Journal Article
• Authors: Monopoli, Antonio; Cotugno, Pietro; Iannone, Francesco; Ciminale, Francesco; Dell'Anna, Maria Michela; Mastrorilli, Piero; Nacci, Angelo
• Is Part Of: European journal of organic chemistry. Issue 27(2014)
• Page Start: 5925
• Page End: 5931
• Publication Date: 2014-08-15
• Subjects: Ionic liquids -- Imines -- Amines -- Oxidation -- Oxygen -- Green chemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402530
• Languages: English
• ISSNs: 1434-193X

Abstract

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. Abstract : An oxidative coupling of amines to give imines in ionic liquids (ILs) under metal‐free aerobic conditions has been developed. The efficiency achievable in ILs is explained in terms of activation of the reactants (benzylamine and O2 ) by an initial electron transfer, promoted by the ionic medium.