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Copper(ii) ions supported on functionalized graphene oxide: an organometallic nanocatalyst for oxidative amination of azolesviaC-H/C-N bond activation

Behzadi, M ; Sharif University of Technology | 2021

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  1. Type of Document: Article
  2. DOI: 10.1039/d0nj02385j
  3. Publisher: Royal Society of Chemistry , 2021
  4. Abstract:
  5. Graphene oxide (GO) was chemically modified withpara-aminobenzoic acid (PABA) to immobilize copper(ii) ions on its surface and used as a nanocatalyst for the oxidative C(sp2)-H bond amination reaction. A practical method to prepare Cu2+supported onpara-aminobenzoic acid grafted on GO was reported. The prepared Cu2+@GO/PABA was characterized by FT-IR, XRD, SEM, AFM, TEM, UV-Vis, and ICP techniques. The results showed that the morphology, distribution, and loading of copper ions could be well-adjusted by grafting of PABA on GO. Moreover, just 2 mol% of Cu2+@GO-PABA could catalyze the C-H activation reaction of benzoxazole and benzothiazole with secondary amines in >94% yields. Also, the catalyst showed very good recyclability and much less leaching of the Cu into the reaction solution. The high activity of Cu2+@GO-PABA can be ascribed to the good synergistic effects of Cu2+andpara-aminobenzoic acid grafted on graphene oxide. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021
  6. Keywords:
  7. Activation analysis ; Amines ; Amino acids ; Chemical activation ; Copper metallography ; Grafting (chemical) ; Graphene ; Metal ions ; Morphology ; Nanocatalysts ; Organometallics ; Amination reaction ; Aminobenzoic acid ; Chemically modified ; Functionalized graphene ; Practical method ; Reaction solutions ; Secondary amines ; Synergistic effect ; Copper compounds ; 4 aminobenzoic acid ; Amine ; Benzothiazole ; Benzoxazole derivative ; Carbon ; Chloroform ; Copper ; Cupric ion ; Graphene oxide ; Hydrogen ; Nanocomposite ; Nanosheet ; Nitrogen ; Pyrrole derivative ; Amination ; Atmosphere ; Catalyst ; Chemical binding ; Chemical bond ; Chemical interaction ; Controlled study ; Deprotonation ; Elemental analysis ; Fourier transform infrared spectroscopy ; Nanocatalyst ; Oxidation ; Priority journal ; Raman spectrometry ; Ring opening ; Scanning electron microscopy ; Synthesis ; Transmission electron microscopy ; Ultraviolet visible spectroscopy
  8. Source: New Journal of Chemistry ; Volume 45, Issue 6 , 2021 , Pages 3242-3251 ; 11440546 (ISSN)
  9. URL: https://pubs.rsc.org/en/content/articlelanding/2021/nj/d0nj02385j