The complex [CoII(4′-MeO-tpy)2](PF6)2 (4′-MeO-tpy = 4′-methoxy-2,2′:6′,2″-terpyridine) effectively mediates the visible-light-driven arylation of pyrroles, 1,3,5-trimethoxybenzene, and bis(pinacolato)diborane (B2Pin2). Mechanistic studies suggest the reaction likely proceeds via a halogen atom transfer mechanism facilitated by an α-aminyl radical. This work highlights the potential of optimizing the ligand framework and reaction conditions to advance the application of earth-abundant transition metal complexes in photoredox catalysis.