Cu-Catalyzed Coupling of Aryl Halides Utilizing Ammonia and Hydroxypicolinamide Ligands

The hydroxypicolinamide family of ligands has previously demonstrated utility in Cu-catalyzed C–N couplings and hydroxylation of heteroaryl halides. The application of these ligands has been extended to the coupling of ammonia with aryl bromides and iodides using the dimethoxy picolinamide scaffold ligand. By tailoring reaction conditions, Cu-DMPS provides high reactivity and selectivity toward amination over hydroxylation. Utilizing aqueous ammonia or anhydrous ammonia with K3PO4 in MeOH provides robust conversion of bromides and iodides to the corresponding aryl amines. Additionally, this catalytic system gives efficient C–N couplings with simple primary amines by using the same general reaction conditions.