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A new Green Iodinating reagent, N‐Iodo‐4‐N,N‐Dimethylaminopyridinium Iodide, is identified, prepared and the structure is unambiguously established. The reagent is employed for metal/coreagent free regioselective mono and also diiodination of phenols and anilines. This is the first report wherein both phenol and aniline regioselectively produced only ortho monoiodo derivatives. Chemoselectivity and nucleo‐selectivity were also gained from this methodology. Our procedure is an Eco‐friendly one due to Good E‐factor (0.27), recovery and recycling of DMAP, Non‐chromatography purification of products and water as solvent.