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Photocatalytic Sonogashira Coupling on Polymeric Pyrazine–CuO Nanoparticles
Supramolecular Ensemble of TICT-AIEE Active Pyrazine Derivative and CuO NPs: A Potential Photocatalytic System for Sonogashira Couplings.
ACS Catal. 2016;
18 August 2016 (online)
Key wordspyrazines - copper oxide - supramolecular assembly - nanoparticles - photocatalysis - Sonogashira–Hagihara cross-coupling
CuO nanoparticles stabilized on a polymeric amine (poly1–CuO NPs) were prepared by treatment of CuCl2 with the benzopyrazine-derived amine 1 in water under air. Poly1-CuO NPs promoted the photocatalytic Sonogashira coupling of aryl halides 2 with ethynylbenzene (3) under visible-light irradiation to give the corresponding products 4 in ≤89% yield.
Poly1–CuO NPs were characterized by means of FT-IR and UV-vis, and fluorescence spectroscopy and XRD, SEM, and TEM analyses. The reaction of iodobenzene with 3 in darkness gave 4a in 30% yield. In the absence of poly1, CuO nanoparticles catalyzed the reaction to give 4a in 48% yield in 12 hours. Poly1–CuO NPs were reused five times without significant loss of their catalytic activity.