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Ionic‐Liquid‐Assisted Metal‐Free Oxidative Coupling of Amines To Give Imines
Author(s) -
Monopoli Antonio,
Cotugno Pietro,
Ian Francesco,
Ciminale Francesco,
Dell'Anna Maria Michela,
Mastrorilli Piero,
Nacci Angelo
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402530
Subject(s) - chemistry , ionic liquid , benzylamine , oxidative coupling of methane , ionic bonding , reactivity (psychology) , solvent , metal , electron transfer , photochemistry , oxidative phosphorylation , oxygen , organic chemistry , catalysis , ion , biochemistry , medicine , alternative medicine , pathology
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.