Regioselective hydroboration of pyridines to 1,2-dihydropyridines remains a significant challenge for the synthesis of valuable nitrogenous bioactive molecules. Herein, we report a base free ligand-controlled cobalt-catalyzed 1,2-hydroboration of pyridines and quinolines with very low catalyst loading under neat reaction conditions. The choice of sterically demanding N-heterocyclic ligands led to the 1,2-regioselectivity and the scope was demonstrated by the N-heterocycles having a variety of functional groups. The preliminary mechanistic studies corroborate that the two ligands followed a distinct catalytic cycle with Co(I) as an active species.