We have discovered an innate, technically simple procedure for direct C-H difluoromethylation of heteroaromatic compounds using off-the-shelf difluoroacetic acid as the difluoromethylating agent in the presence of silver nitrate and potassium persulfate as the preferred oxidant following a Minisci-type reaction pathway. The reaction is tunable as bi-difluoromethylated products can be obtained by controlling the reaction temperature and running the reaction under more forceful conditions. Herein, we wish to report our detailed investigations, mechanistical studies and the scope, limitations and perspective of this novel reaction for both pi-deficient as well as pi-excessive heterocycles as well as unfold and deploy this methodology for preparation of tool compounds for chemical biology and provide access to this hitherto untapped substituent in drug discovery.