Throughout our investigations, we were surprised to continually reaffirm the results of ONSH outcompeting SNAr. We decided to test the limits of this competition in the electrophile scope by using 2-fluoro-4-nitropyridine, which is more primed for SNAr than 2a, yet that substrate afforded 5u in similar yield to 5a! When the 2-fluoro group was replaced with the bulkier 2bromo, 5v was formed as the major product but in reduced yield, presumably due to steric encumbrance. A similar effect was noted in the case of 2,6-dichloro-4-nitropyridine 5w. With nitrobenzenes as substrates instead of nitropyridines, UPLC/MS traces of the crude reaction mixture showed significantly more byproducts, and the isolated yields of 5z and 5aa were lower compared to the analogous nitropyridine products. Five-membered nitro(hetero)arenes were also tolerated, including thiophene 5ab and pyrazole 5ac. Imidazoles, while lowyielding, were also competent electrophiles, including the antiparasitic drug metronidazole (5ad-ae). 12 Scheme 3. Substrate scope of nitro(hetero)arene amination.