Reported the cobalt(II)-catalyzed C-H alkylation and acylation of N-heterocycles with 1,4-dihydropyridines (DHPs) as alkylating and acylating agents.Notably, a combination of KBrO3 and a Co(II) catalyst were successfully employed for the generation of alkyl and acyl radicals from DHPs.A series of heterocycles, including azauracils, quinoxalinones, pyrazinones, pyridones, quinolones, quinazolinones, xanthines, chromones and azine N-oxides, were compatible under the developed conditions.The applicability of the developed protocol in challenging contexts is highlighted by the selective modification of drug candidates as well as the gram-scale synthesis of bioactive mols.Combined mechanistic investigations aided the elucidation of a plausible reaction mechanism.