Iron-Catalyzed C–N Coupling Using Polycyclic Aromatic Hydrocarbon as a Redox Mediator

Arylamines play a critical role in organic electronics, agrochemicals, and pharmaceuticals, with rapid advancements in their synthesis realized through palladium-catalyzed C-N coupling since the 1980s. Nonetheless, systems utilizing first-row transition metals remain underdeveloped regardless of their potential in future chemical synthesis. Herein, we report that iron catalyzes C-N coupling of aryl halides with carbazole and aryl amine amides in the presence of polycyclic aromatic hydrocarbon (PAH) as a redox mediator. The proposed mechanism involves Fe(II) species undergoing single-electron transfer (SET) via PAH, which promotes the activation of aryl halides and the generation of reactive intermediates. This approach leverages PAH to enable efficient iron-catalyzed C-N coupling, offering potential for broader substrate applicability and applications in materials science.