Aryne Aminohalogenation Using Protic Amines Enabled by Halogen Transfer

Methods for aryne difunctionalization have been the focus of recent research, but one limitation is the use of nucleophiles with proton sources. Herein, we demonstrate the use of halogen transfer reagents to enable protic amines in aryne aminohalogenation difunctionalizations in up to 86% yield. This method uses amines and arynes with a variety of N-heterocyclic scaffolds. Through a variety of derivatizations, the synthetic utility of these products is demonstrated.