A novel palladium-catalyzed protocol for the monoarylation of cyclopropylamine using the sterically demanding and electron-rich adamantyl-substituted ylide-functionalized phosphine (YPhos) adYPhos is reported. This method enables the efficient coupling of a wide range of (hetero)aryl chlorides at room temperature. The reported ligand enhances the scope for the application of YPhos ligands in amination reactions on more challenging substrates. The protocol is versatile, accommodating various functional groups and extending to larger cycloalkylamines, all accessible under feasible and mild conditions.