Synthesis of amine derivatives from a "one-pot" synthesis of biphenyl-4-methylazide

Abstract

This thesis explores the synthesis of amine derivatives such as amides and imines from biphenyl-4-methylazide using Staudinger chemistry. A robust one-pot synthesis of biphenyl-4-methylazide was first achieved through the use of p-nitrobenzenesulfonyl azide as the azide source. 1,2-Bis(diphenylphosphino)ethane (DPPE), which is cost-effective and readily available, was utilized as the mild phosphorus reducing agent. Over 40 examples of imines and amides have been synthesized producing yields as high as 70%.