Hg cathode-free electrochemical detosylation of N,N-disubstituted p-toluenesulfonamides: mild, efficient, and selective removal of N-tosyl group

Hg cathode-free electrochemical detosylation of N,N-disubstituted p-toluenesulfonamides was successfully carried out by a constant Current electrolysis using an undivided cell equipped with a platinum cathode and a magnesium anode in the presence of an arene mediator. The deprotection proceeded efficiently and selectively under neutral and mild conditions with a stoichiometric amount of electricity without the use of an Hg cathode to obtain the corresponding secondary amines in good to excellent yields. (C) 2009 Elsevier Ltd. All rights reserved.