Over the past decade, iron (Fe) catalysis has gained significant attention in synthetic chemistry 14 by providing an attractive avenue for developing efficient methodologies to streamline the synthesis of complex organic molecules, 15 due to its cost-effectiveness, biocompatibility and environmental sustainability. While Fe-catalyzed multicomponent reactions offer unique opportunities beyond conventional transition-metal catalysis, 16 the application of inexpensive iron catalysts in three-component 1,2-aryl heteroatom functionalization of alkenes for constructing bioactive small molecules is still underdeveloped. In 2023, Leboeuf and co-workers reported a Fe-catalyzed two-step 1,2-aminoarylation of alkenes with arenes and hydroxylamines as the nitrogen source through a ring-opening strategy via an aziridinium intermediate. However, the scope of the reaction is limited to electron-deficient alkenes and electron-rich arenes. Therefore, there is still a need for more general ways to promote 1,2-aryl heteroatom functionalization of alkenes starting from commercially available aromatics and alkenes of diverse electronic/steric attributes. In this context, metallaphotoredox, the merger of photoredox and transition metal catalysis, has emerged as a promising strategy by offering a broader scope and greater generality. Recently, Gaunt and co-workers demonstrated the use of a photoredox/iron catalytic approach for the vicinal arylchlorination of vinylboronic esters using diaryliodonium salts as the aryl radical source. Building upon this concept, we report a mild, modular, and practical photoredox/iron dual catalytic system by leveraging aryl sulfonium salts as versatile building blocks, readily accessible from arenes in a regioselective manner. This system demonstrates a broad substrate scope, tolerating various (hetero)arenes, alkenes, and heteroatomic compounds, thereby providing a versatile platform for the synthesis of diverse 1,2-aryl heteroatomic pharmacophores (Figure ). Additionally, this mild photoredox/iron dual-catalytic system offers a convenient method for the underdeveloped direct generation of 1,2-alkenyl heteroatomic compounds, an important class of medicinally relevant scaffolds that include homoallylamines (Figure ), using alkenes as the alkenyl radical precursors.