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.