Abstract
Magnetic chitosan/Cu–Mg–Al layered double hydroxide (mCSLDH) nanocomposite was prepared and copper(II) ions were immobilized in the prepared composite. The nanocomposite [(Cu-mCSLDH)] was characterized by FT-IR, XRD, VSM, AAS, EDX, SEM and TEM. The utility of nanocomposite was investigated in the one-pot three-component (A3) coupling of aldehydes, amines and alkynes to produce propargylamines. The Cu-mCSLDH nanocomposite is found to be highly efficient and recyclable heterogeneous catalyst.
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J. Kredatusová, H. Beneš, S. Livi, O. Pop-Georgievski, P. Ecorchard, S. Abbrent, E. Pavlova, D. Bogdał, Influence of ionic liquid-modified LDH on microwave-assisted polymerization of ε-caprolactone. Polymer 100, 86–94 (2016)
Q. Wang, D. O’Hare, Recent advances in the synthesis and application of layered double hydroxide (LDH) nanosheets. Chem. Rev. 112, 4124–4155 (2012)
J. Yu, J.E. Sims, L. Sun, In situ synthesis of polyelectrolyte/layered double hydroxide intercalation compounds. J. Mater. Sci. 52, 6647–6655 (2017)
M. Yadollahi, H. Namazi, M. Aghazadeh, Antibacterial carboxymethyl cellulose/Ag nanocomposite hydrogels cross-linked with layered double hydroxides. Int. J. Biol. Macromol. 79, 269–277 (2015)
A.I. Tsyganok, K. Suzuki, S. Hamakawa, K. Takehira, T. Hayakawa, Mg–Al layered double hydroxide intercalated with [Ni (edta)] 2—chelate as a precursor for an efficient catalyst of methane reforming with carbon dioxide. Catal. Lett. 77, 75–86 (2001)
G. Varga, Z. Timár, S. Muráth, Z. Kónya, Á Kukovecz, S. Carlson, P. Sipos, I. Pálinkó, Syntheses, characterization and catalytic activities of CaAl-layered double hydroxide intercalated Fe(III)-amino acid complexes. Catal. Today (2016). https://doi.org/10.1016/j.cattod.2016.12.005
G. Varga, Á Kukovecz, Z. Kónya, L. Korecz, S. Muráth, Z. Csendes, G. Peintler, S. Carlson, P. Sipos, I. Pálinkó, Mn(II)–amino acid complexes intercalated in CaAl-layered double hydroxide—well-characterized, highly efficient, recyclable oxidation catalysts. J. Catal. 335, 125–134 (2016)
G. Varga, S. Ziegenheim, S. Muráth, Z. Csendes, Á Kukovecz, Z. Kónya, S. Carlson, L. Korecz, E. Varga, P. Pusztai, Cu(II)-amino acid–CaAl-layered double hydroxide complexes, recyclable, efficient catalysts in various oxidative transformations. J. Mol. Catal. A 423, 49–60 (2016)
M. Yang, Z. Zhang, J. Ma, L. Liu, M. Wang, B. Pan, J. Li, J. Xu, Z. Tong, Fabrication of intercalation hybrid of Ni–Al layered double hydroxide with Cu(II) phthalocyanine via exfoliation/restacking route and photocatalytic activity on elimination of Rhodamine 6G. J. Incl. Phenom. Macrocycl. Chem. 87, 117–125 (2017)
S. Kumari, S. Layek, D.D. Pathak, Chitosan supported Zn(II) mixed ligand complexes as heterogeneous catalysts for one-pot synthesis of amides from ketones via Beckmann rearrangement. J. Mol. Struct. 1130, 368–373 (2017)
S. Adewuyi, I. Bisiriyu, C. Akinremi, S. Amolegbe, Synthesis, spectroscopic, surface and catalytic reactivity of chitosan supported Co(II) and Its zerovalentcobalt nanobiocomposite. J. Inorg. Organomet. Polym. Mater. 27, 114–121 (2017)
D.R. Vakilabadi, A.H. Hassani, G. Omrani, B. Ramavandi, Catalytic potential of Cu/Mg/Al-chitosan for ozonation of real landfill leachate. Process Saf. Environ. Prot. 107, 227–237 (2017)
L. Shiri, L. Heidari, M. Kazemi, Magnetic Fe3O4 nanoparticles supported imine/thiophene-nickel(II) complex: a new and highly active heterogeneous catalyst for the synthesis of polyhydroquinolines and 2,3-dihydroquinazoline-4 (1H)-ones. Appl. Organomet. Chem. (2017) https://doi.org/10.1002/aoc.3943
Z. Li, Y. Du, Z. Zhang, D. Pang, Preparation and characterization of CdS quantum dots chitosan biocomposite. React. Funct. Polym. 55, 35–43 (2003)
J. Barrault, A. Derouault, G. Courtois, J. Maissant, J. Dupin, C. Guimon, H. Martinez, E. Dumitriu, On the catalytic properties of mixed oxides obtained from the Cu-Mg-Al LDH precursors in the process of hydrogenation of the cinnamaldehyde. Appl. Catal. A 262, 43–51 (2004)
L. Liu, C. Li, C. Bao, Q. Jia, P. Xiao, X. Liu, Q. Zhang, Preparation and characterization of chitosan/graphene oxide composites for the adsorption of Au(III) and Pd(II). Talanta 93, 350–357 (2012)
B. Guo, Y. Zhao, Q. Huang, Q. Jiao, A new method to prepare exfoliated UV-cured polymer/LDH nanocomposites via nanoplatelet-like LDHs modified with N-lauroyl-glutamate. Compos. Sci. Technol. 81, 37–41 (2013)
K.R. Reddy, K.-P. Lee, A.I. Gopalan, H.-D. Kang, Organosilane modified magnetite nanoparticles/poly(aniline-co-o/m-aminobenzenesulfonic acid) composites: synthesis and characterization. React. Funct. Polym. 67, 943–954 (2007)
J. Dulle, K. Thirunavukkarasu, M.C. Mittelmeijer-Hazeleger, D.V. Andreeva, N.R. Shiju, G. Rothenberg, Efficient three-component coupling catalysed by mesoporous copper–aluminum based nanocomposites. Green Chem. 15, 1238–1243 (2013)
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Partial funding support was provided by the Research Council of University of Maragheh (M.A.) and University of Tehran (S.M.F.).
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Nikkhoo, M., Amini, M., Farnia, S.M.F. et al. Preparation and Characterization of Magnetic Chitosan/Cu–Mg–Al Layered Double Hydroxide Nanocomposite for the One-Pot Three-Component (A3) Coupling of Aldehydes, Amines and Alkynes. J Inorg Organomet Polym 28, 2028–2035 (2018). https://doi.org/10.1007/s10904-018-0861-4
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DOI: https://doi.org/10.1007/s10904-018-0861-4