Difunctionalization of alkenes represents a powerful synthetic strategy to build molecular complexity. In the last decade, the use of alkenes in transition metal-catalyzed multicomponent cross-coupling reactions has emerged as an efficient and modular method to access diverse molecular structures, including fluoroalkylated compounds, through the simultaneous construction of two new bonds across the p system. 2 Fluoroalkylated compounds are appealing due to the properties of the difluoromethylene group (-CF2-) and derivatives that can, inter alia, induce conformation changes, increase dipole moments, and modulate the acidity of neighboring C-H bonds. Notably, some perfluoroalkyl-substituted compounds have shown more exceptional properties than the CF3 or CF2H substituents. Recently, Zhang and Nevado 6d reported the use of enamides as effective lynchpins in nickel-catalyzed threecomponent cross-coupling reactions (Scheme 1A). However, a major drawback of these methods is the need for long reaction times, high temperatures, and/or limited substrate scope. Further, despite the importance of N-alkylated phthalimides and, in particular, widespread application in the practical synthesis of amines, the use of N-vinylphthalimide in these transition-metal catalyzed crosscoupling reactions has been severely limited. Iron is an attractive transition metal catalyst in cross-coupling reactions due to its low cost, abundance within the Earth's crust, and lower toxicity in comparison to traditional palladium and nickel systems. 9 Previously, our group reported the use of iron catalysts to promote threecomponent cross-coupling reactions with a-heteroatom alkyl radicals including a-boryl and a-alkoxy radicals. Inspired by this work and recent works using nickel catalysts by the Zhang and Nevado groups (Scheme 1A; inset), we hypothesized that bisphosphine-iron complexes could serve as effective catalysts to promote fluoroalkylarylation of enamides via selective formation and cross-coupling of aamide radicals (Scheme 1B). If successful, such approach would provide a complementary approach to nickel-based systems and expand the utility of iron-catalysts in multicomponent cross-couplings. Herein, we describe the first examples of an iron-catalyzed three-component cross-coupling of N-vinyl π-systems including N-vinylphthalimides, N-vinyl lactams, N-vinyloxazolidinone and N-vinylacetamides with readily available fluoroalkyl bromides and aryl Grignard reagents.