The oxidative aminative vicinal difunctionalization of alkenes or related chemical feedstocks has emerged as sustainable and multipurpose strategies that can efficiently construct two −N bonds, and simultaneously prepare the synthetically fascinating molecules and catalysis in organic synthesis that typically required multi‐step reactions. This review summarized the impressive breakthroughs on synthetic methodologies (2015‐2022) documented especially over inter/intra‐molecular vicinal diamination of alkenes with electron‐rich or deficient diverse nitrogen sources. These unprecedented strategies predominantly involved iodine‐based reagents/catalysts, which resent the interest of organic chemists due to their impressive role as flexible, non‐toxic, and environmentally friendly reagents, resulting in a wide variety of synthetically useful organic molecules. Moreover, the information collected also describes the significant role of catalyst, terminal oxidant, substrate scope, synthetic applications, and their unsuccessful results to highlight the limitations. Special emphasis has been given to proposed mechanistic pathways to determine the key factors governing the issues of regioselectivity, enantioselectivity, and diastereoselectivity ratios.