A Lewis acid mediated schmidt reaction of benzylic azide: Synthesis of sterically crowded aromatic tertiary amines

…, M Puppala, B Varghese, S Baskaran

Index: Murali, Annamalai; Puppala, Manohar; Varghese, Babu; Baskaran, Sundarababu European Journal of Organic Chemistry, 2011 , # 27 p. 5297 - 5302

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Abstract

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 EtAlCl 2, benzylic azide underwent a smooth Schmidt reaction to give the corresponding iminium ion, which, upon reduction with NaBH 4 in situ, afforded the tertiary amine. The effects of substituents on the aromatic ring and the steric effects of the alkyl ...