A Lewis Acid Mediated Schmidt Reaction of Benzylic Azide: Synthesis of Sterically Crowded Aromatic Tertiary Amines

✍ Scribed by Annamalai Murali; Manohar Puppala; Babu Varghese; Sundarababu Baskaran

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 451 KB
• Volume: 2011
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201100674

✦ Synopsis

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 side chain have also been studied.