Gram-Scale Synthesis of Polymeric Carbon Nitride-Supported Copper: A Practical Catalyst for Ullmann-Type C-N Coupling Modifying Secondary Pyrimidin-2-amines without Additional Ligand

Cu/polymeric carbon nitride (PCN) can be prepared in 10 g scale by calcining Cu(NO3)(2) with the melamine precursor at 550 degrees C. X-ray photoelectron spectroscopy (XPS) analysis demonstrated that copper in the material was in Cu(I) form and it could catalyze the Ullmann-type C-N coupling reactions of pyrimidin-2-amine derivatives with aryl halides without additional ligand. As a heterogeneous catalyst, the material was recoverable and could be reused for at least five times without deactivation. This material was found to be even more active than traditional Cu(I) catalysts and Pd catalysts, affording an opportunity to develop the efficient and practical novel catalyst reagent for the synthesis of medicines containing pyrimidin-2-amine moieties in pharmaceutical industry.

Automated summary

Cu/polymeric carbon nitride (PCN) prepared by calcining Cu(NO3)(2) with the melamine precursor at 550 degrees C can catalyze the Ullmann-type C-N coupling reactions. The material is more active than traditional Cu(I) and Pd catalysts, offering an opportunity for developing efficient novel catalysts for synthesis of medicines containing pyrimidin-2-amine moieties.