The rapid and efficient construction of molecular complexity from readily available starting materials has long been a fundamental pursuit in organic synthesis. In recent decades, transition-metal catalysis, photocatalysis, and electrosynthesis have emerged as powerful strategies for alkene difunctionalization, enabling the construction of two neighboring chemical bonds in a single transformation (Figure ). 1 Among these vicinal difunctionalizations, alkene 1,2-aryl heteroatom functionalization is of particular interest as it enables straightforward and step-economic synthesis of structurally diverse products by introducing a C-X bond (X = N, O, S, halogens, etc.) and a C-C(sp 2 ) bond simultaneously. Furthermore, the incorporation of the 1,2-aryl heteroatomic motif has demonstrated enhancement in bio-efficacy and therapeutic potential, rendering it a privileged scaffold in pharmaceutical development 3 (Figure ). Although several transition-metal-catalyzed strategies for multicomponent 1,2-aryl heteroatom functionalization of alkenes have been developed, including carboboration 4 and arylhalogenation, 5 oxidative oxyarylation, 6 arylsulfenylation, and the synthesis of cyclic arylethylamines, 8 most of these methods are limited by their narrow substrate scopes and the need for tailored directing groups, thus hindering their broad applicability.