<p>Nitration of 2-arylimidazo[1,2-<i>a</i>]pyridines has been successfully carried out using a fast, straightforward, and one-step method. This innovative strategy was rigorously examined, focusing on the exclusive use of hypervalent iodine reagents or metallic salts under aqueous, non-aqueous conditions and grinding methods; ultimately leading to the desired outcomes through the combined use of widely used hypervalent iodine reagent iodobenzene diacetate and inexpensive copper nitrate trihydrate using organic solvent dichloromethane at room temperature. Herein, the iodobenzene diacetate reagent act as oxidant and copper nitrate as catalyst as well as the nitro group source. The model reaction method was expanded to a variety of substrates with different electron withdrawing and electron donating groups providing regioselective <i>ortho</i>-nitrated 2-arylimidazo[1,2-<i>a</i>]pyridines in significant yields. Further, the elucidation of the novel nitrated products was meticulously validated using a comprehensive array of analytical tools,¹H-NMR, ¹³C-NMR, FT-IR, and mass spectral analysis. We conducted controlled experiments by blocking one of the possible attacking C-3 site to determine the specific product formed. The introduction of nitro functional group was facilitated through <i>ortho</i> C(<i>sp</i>^<i>2</i>)-H activation strategy and the plausible mechanism for the nitration process has been proposed. Overall, the successful implementation of this methodology underscores its potential significance in advancing the synthesis of functionalized heterocycles.</p> Graphical abstract <p></p>