Oxidative Functionalization of Amines Using an Electrocatalytic Aminoxyl-Mediated Reaction: Preparation of N-Benzylidenebenzylamines from Benzylamines

A methodology is reported for the preparation of imines from amines by means of an electrocatalytic aminoxyl-mediated reaction. It is performed using readily available electrodes in a commercially available electrochemistry apparatus and does not require the use of a reference electrode. The methodology proceeds under mild conditions and delivers good to excellent isolated yields across a range of structurally diverse benzyl amines. Selectivity is high, with imines obtained in preference to the more commonly reported nitriles, and the process is readily scalable to the gram level. Operational simplicity and short reaction times make this method a valuable addition to the organic chemist's toolkit.