Options
A Lewis acid mediated schmidt reaction of benzylic azide: Synthesis of sterically crowded aromatic tertiary amines
Date Issued
01-09-2011
Author(s)
Murali, Annamalai
Puppala, Manohar
Varghese, Babu
Indian Institute of Technology, Madras
Abstract
An efficient one-pot synthesis of sterically hindered aromatic tertiary amines through Lewis acid induced intermolecular Schmidt reaction of benzylic azides is described. In the presence of EtAlCl2, benzylic azide underwent a smooth Schmidt reaction to give the corresponding iminium ion, which, upon reduction with NaBH4 in situ, afforded the tertiary amine. The effects of substituents on the aromatic ring and the steric effects of the alkyl side chain have also been studied. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.