Aryne-mediated synthesis of sterically hindered arylamines using TEMPO as the amine source

Abstract

Herein, an aryne-mediated synthesis of sterically hindered arylamines using 2,2,6,6-tetramethylpiperidoxyl (TEMPO) as the amine source is reported. Mechanistic studies suggest that TEMPO adds to the aryne to form an aryl radical, which abstracts a hydrogen atom and then undergoes deoxygenation to afford the arylamine. This unprecedented radical process in aryne chemistry offers a concise route to sterically hindered arylamines.