articleJournal of the American Chemical SocietyMay 20, 2025Closed access

Multiple Secondary Bond-Mediated C–N Coupling over N-Doped Carbon Electrocatalysts

Chinese Academy of Sciences · Beijing National Laboratory for Molecular Sciences · +2 more institutions

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Abstract

Electrocatalytic C–N reductive coupling offers a sustainable and eco-friendly approach to producing value-added oximes. The challenge lies in the overstrong chemisorption of N-containing intermediates and carbonyl compounds on metal-based catalysts, which causes low Faradaic efficiency and yield rates, as well as undesired byproducts. Here, we propose a multiple secondary bond-mediated strategy for C–N coupling toward benzaldoxime on a nitrogen-doped graphene-like carbon catalyst (NC). Integrating theoretical and experimental analyses, we demonstrate that the graphitic-N–C sites in NC promote nitrite reduction into hydroxylamine via weak electrostatic interaction. Moreover, the hydrogen bonds and π–π stacking…

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