Incorporation of an electron-withdrawing methoxy group at the meta-position resulted in a high yield of 92% for product 3h. Furthermore, product 3i housing a borylated aromatic moiety, well-suited for Suzuki-Miyaura cross-coupling reactions, was obtained with an excellent yield of 81%. The conditions also applied to heteroaromatic starting materials, including 1j and 1k. Here, product 3j, derived from DMAP, was obtained in 95% yield and product 3k containing a chloro-substituted pyrazine moiety for further functionalization was well-tolerated and was obtained in 64%. Additional studies were conducted to assess the steric restraints of the developed protocol. Notably, the ortho-methyl-containing substrate 1l yielded product 3l in 71% yield. Moreover, the highly sterically-encumbered diisopropyl product 3m was successfully obtained in 62% yield. Despite the resonance through both rings, rendering the oxidation event of the nitrogen lone pair more recalcitrant, the diarylated methyl aniline furnished product 3n in good yield (64%). Scheme 1. Reaction scope of aromatic amines in radical α-amino C-H bond activation.