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Copper Dispersed Covalent Organic Framework for Azide–Alkyne Cycloaddition and Fast Synthesis of Rufinamide in Water

Fei Xue, Jun Zhang, Zhongcheng Ma, Zhonggang Wang

2024Small11 citationsDOI

Abstract

) and uniform mesopore (4.0 nm) is successfully synthesized from 1,3,5-tris-(4'-formyl-biphenyl-4-yl)triazine and 5,5'-diamino-2,2'-bipyridine via a solvothermal method. After Cu(I)-loading, the resultant Cu(I)-Bpy-COF remained the ordered porous structure with evenly distributed Cu(I) ions at a single-atom level. Using Cu(I)-Bpy-COF as a heterogeneous catalyst, high conversions for cycloaddition reactions are achieved within a short time (40 min) at 25 °C in water medium. Moreover, Cu(I)-Bpy-COF proves to be applicable for aromatic and aliphatic azides and alkynes bearing various substituents such as ester, hydroxyl, amido, pyridyl, thienyl, bulky triphenylamine, fluorine, and trifluoromethyl groups. The high conversions remain almost constant after five cycles. Additionally, the antiepileptic drug (rufinamide) is successfully prepared by a simple one-step reaction using Cu(I)-Bpy-COF, proving its practical feasibility for pharmaceutical synthesis.

Topics & Concepts

CycloadditionAlkyneAzideBipyridineChemistryCovalent organic frameworkTriazineCopperBiphenylCatalysisCovalent bondMesoporous materialPolymer chemistryMaterials scienceOrganic chemistryCrystal structureCovalent Organic Framework ApplicationsMetal-Organic Frameworks: Synthesis and ApplicationsAdenosine and Purinergic Signaling