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Synfacts 2016; 12(09): 0977
DOI: 10.1055/s-0035-1562749
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Photocatalytic Sonogashira Coupling on Polymeric Pyrazine–CuO Nanoparticles

Contributor(s):
Yasuhiro Uozumi
,
Yoichi M. A. Yamada
,
Aya Ohno
Deol H, Pramanik S, Kumar M, Khan IA, Bhalla V * Guru Nanak Dev University, Amritsar, India
Supramolecular Ensemble of TICT-AIEE Active Pyrazine Derivative and CuO NPs: A Potential Photocatalytic System for Sonogashira Couplings.

ACS Catal. 2016;
6: 3771-3783
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Further Information

Publication History

Publication Date:
18 August 2016 (online)

 
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Key words

pyrazines - copper oxide - supramolecular assembly - nanoparticles - photocatalysis - Sonogashira–Hagihara cross-coupling

Significance

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.


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Comment

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.


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