Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Two Schiff-base Complexes of Copper and Zirconium Oxide Fabricated on Magnetic Nanoparticles as Practical and Recyclable Catalysts in C-C Coupling Reaction

Author(s): Mohsen Nikoorazm* and Masoomeh Naseri

Volume 18, Issue 7, 2021

Published on: 08 September, 2020

Page: [561 - 573] Pages: 13

DOI: 10.2174/1570178617999200908092916

Price: $65

Abstract

Fe3O44 magnetic nanoparticles (MNPs) were prepared via a chemical co-precipitation method. Then, the surface of Fe3O44 MNPs was modified by (3-Chloropropyl)trimethoxysilane and then two Schiffbase complexes of zirconium oxide and copper were stabilized on modified Fe3O44 MNPs. These catalysts were characterized using SEM, EDS, WDX, FTIR, XRD, TGA, VSM and AAS techniques. The catalytic activity of these catalysts was described in the carbon-carbon coupling reaction. VSM analysis of these catalysts indicates the high magnetic performance; therefore these catalysts can be recovered by an external magnet and reused several times without reducing the number of catalysts. Reusability, excellent yields and high TON values indicate the high efficiency of these catalysts. Leaching of these catalysts was studied by AAS which leaching of copper or zirconium was not observed. Also, the stability of these catalysts was confirmed by the characterization of recovered catalysts and comparing to fresh catalysts.

Keywords: Copper, zirconium oxide, magnetic nanoparticles, C-C coupling reaction, biphenyl, Schiff-base complexes.

Graphical Abstract
[1]
Prieto, G.; Tüysüz, H.; Duyckaerts, N.; Knossalla, J.; Wang, G.H.; Schüth, F. Chem. Rev., 2016, 116(22), 14056-14119.
[http://dx.doi.org/10.1021/acs.chemrev.6b00374] [PMID: 27712067]
[2]
Benaglia, M.; Puglisi, A.; Cozzi, F. Chem. Rev., 2003, 103(9), 3401-3429.
[http://dx.doi.org/10.1021/cr010440o] [PMID: 12964876]
[3]
Vece, V.; Szeto, K.C.; Charlin, M.O. Catal. Commun., 2019, 129, 105715.https://doi.org/https://doi.org/10.1016/j.catcom.2019.105715
[http://dx.doi.org/10.1016/j.catcom.2019.105715]
[4]
Dhakshinamoorthy, A.; Santiago-Portillo, A.; Asiri, A.M.; Garcia, H. ChemCatChem, 2019, 11, 899-923.
[http://dx.doi.org/10.1002/cctc.201801452]
[5]
Tahmasbi, B.; Ghorbani-Choghamarani, A. New J. Chem., 2019, 43, 14485-14501.
[http://dx.doi.org/10.1039/C9NJ02727K]
[6]
Nikoorazm, M.; Ghorbani-Choghamaranai, A.; Khanmoradi, M.; Moradi, P. J. Porous Mater., 2018, 25, 1831-1842.
[http://dx.doi.org/10.1007/s10934-018-0597-0]
[7]
Nikoorazm, M.; Ghorbani-Choghamarani, A.; Panahi, A.; Tahmasbi, B.; Noori, N. J Iran Chem Soc, 2018, 15, 181-189.
[http://dx.doi.org/10.1007/s13738-017-1222-x]
[8]
Anuma, S.; Mishra, P.; Bhat, B.R. J Taiwan Inst. Chem. Eng., 2019, 95, 643-651.
[http://dx.doi.org/10.1016/j.jtice.2018.09.029]
[9]
Key, R.J.; Tengco, J.M.M.; Smith, M.D.; Vannucci, A.K. Organometallics, 2019, 38, 2007-2014.
[http://dx.doi.org/10.1021/acs.organomet.9b00082]
[10]
Ghorbani-Choghamarani, A.; Moradi, P.; Tahmasbi, B. J Iran Chem Soc, 2019, 16, 511-521.
[http://dx.doi.org/10.1007/s13738-018-1526-5]
[11]
Hamdi, J.; Blanco, A.A.; Diehl, B.; Wiley, J.B.; Trudell, M.L. Org. Lett., 2019, 21(10), 3471-3475.
[http://dx.doi.org/10.1021/acs.orglett.9b00042] [PMID: 30942602]
[12]
Chen, M-N.; Mo, L-P.; Cui, Z-S.; Zhang, Z-H. Curr Opin Green Sustain Chem, 2019, 15, 27-37.https://doi.org/https://doi.org/10.1016/j.cogsc.2018.08.009
[13]
J Iran Chem Soc, 2019, 16, 365-372.
[14]
Gilanizadeh, M.; Zeynizadeh, B.; Gholamiyan, E. Iran. J. Sci. Technol. Trans. A Sci., 2019, 43, 819-827.
[http://dx.doi.org/10.1007/s40995-018-0594-9]
[15]
Afsar, J.; Khazaei, A.; Zarei, M.; Zolfigol, M.A. ChemistrySelect, 2019, 4, 1122-1126.
[http://dx.doi.org/10.1002/slct.201803212]
[16]
Shiri, L.; Tahmasbi, B. Phosphorus Sulfur Silicon Relat. Elem., 2017, 192.
[http://dx.doi.org/10.1080/10426507.2016.1224878]
[17]
Ghorbani-Choghamarani, A.; Tahmasbi, B.; Noori, N.; Faryadi, S. C. R. Chim., 2017, 20, 132-139.
[http://dx.doi.org/10.1016/j.crci.2016.06.010]
[18]
Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H.; Bouhrara, M.; Basset, J.M. Chem. Rev., 2011, 111(5), 3036-3075.
[http://dx.doi.org/10.1021/cr100230z] [PMID: 21401074]
[19]
Lim, C.W.; Lee, I.S. Nano Today, 2010, 5, 412-434.
[http://dx.doi.org/10.1016/j.nantod.2010.08.008]
[20]
Ghorbani-Choghamarani, A.; Moradi, P.; Tahmasbi, B. Polyhedron, 2019, 163, 98-107.
[http://dx.doi.org/10.1016/j.poly.2019.02.004]
[21]
Trzeciak, A.M.; Augustyniak, A.W. Coord. Chem. Rev., 2019, 384, 1.
[http://dx.doi.org/10.1016/j.ccr.2019.01.008]
[22]
Liu, Y.; Bai, X.; Li, S. Microporous Mesoporous Mater., 2018, 260, 40.
[http://dx.doi.org/10.1016/j.micromeso.2017.06.006]
[23]
Matsumoto, H.; Akiyoshi, T.; Hoshino, Y.; Seto, H.; Miura, Y. Polym. J., 2018, 50, 1179.
[http://dx.doi.org/10.1038/s41428-018-0102-2]
[24]
Gaikwad, D.S.; Undale, K.A.; Patil, D.B.; Pore, D.M. J. Iran. Chem. Soc., 2019, 16, 253.
[http://dx.doi.org/10.1007/s13738-018-1503-z]
[25]
Tahmasbi, B.; Ghorbani-Choghamarani, A.; Moradi, P. New J. Chem., 2020, 44, 3717-3727.
[http://dx.doi.org/10.1039/C9NJ06129K]
[26]
Sardarian, A.R.; Kazemnejadi, M.; Esmaeilpour, M. Dalton Trans., 2019, 48(9), 3132-3145.
[http://dx.doi.org/10.1039/C9DT00060G] [PMID: 30775761]
[27]
Ghonchepour, E.; Islami, M.R.; Momeni Tikdari, A. J. Organomet. Chem., 2019, 883, 1.
[http://dx.doi.org/10.1016/j.jorganchem.2019.01.008]
[28]
He, Z.; Song, F.; Sun, H.; Huang, Y. J. Am. Chem. Soc., 2018, 140(7), 2693-2699.
[http://dx.doi.org/10.1021/jacs.8b00380] [PMID: 29360376]
[29]
Moradi, P.; Hajjami, M.; Valizadeh‐Kakhki, F. Appl. Organomet. Chem., 2019, 33, e5205.
[http://dx.doi.org/10.1002/aoc.5205]
[30]
Gaikwad, D.S.; Undale, K.A.; Patil, D.B.; Pore, D.M. Inorg. Chim. Acta, 2018, 471, 345.
[http://dx.doi.org/10.1016/j.ica.2017.11.018]
[31]
Dolatkhah, Z.; Javanshir, S.; Bazgir, A. J. Iran. Chem. Soc., In press
[http://dx.doi.org/10.1007/s13738-019-01625-2]
[32]
Sarhid, I.; Abdellah, I.; Martini, C.; Huc, V.; Dragoe, D.; Beaunier, P.; Lampre, I.; Remita, H. New J. Chem., 2019, 43, 4349.
[http://dx.doi.org/10.1039/C8NJ06370B]
[33]
Tahmasbi, B.; Ghorbani-Choghamarani, A.; Hudson, R.H.E.; Heidari, A. Microporous Mesoporous Mater., 2019, 284, 366-377.
[http://dx.doi.org/10.1016/j.micromeso.2019.04.061]
[34]
Nikoorazm, M.; Noori, N.; Tahmasbi, B.; Faryadi, S. Transit Met Chem, 2017, 42, 469-481.
[http://dx.doi.org/10.1007/s11243-017-0151-y]
[35]
Jabbari, A.; Tahmasbi, B.; Nikoorazm, M.; Ghorbani‐Choghamarani, A. Appl. Organomet. Chem., 2018, 32, e4295.
[http://dx.doi.org/10.1002/aoc.4295]
[36]
Nikoorazm, M.; Ghobadi, M. Silicon, 2019, 11, 983-993.
[http://dx.doi.org/10.1007/s12633-018-9871-7]
[37]
Nikoorazm, M.; Moradi, P.; Noori, N. J. Porous Mater., 2020, 27, 1159-1169.
[http://dx.doi.org/10.1007/s10934-020-00894-0]
[38]
Moradi, P.; Hajjami, M.; Tahmasbi, B. Polyhedron, 2020, 175, 114169.
[http://dx.doi.org/10.1016/j.poly.2019.114169]
[39]
Nikoorazm, M.; Rezaei, Z.; Tahmasbi, B. J. Porous Mater., 2020, 27, 671-689.
[http://dx.doi.org/10.1007/s10934-019-00835-6]
[40]
Patel, H.A.; Patel, A.L.; Bedekar, A.V. Appl. Organomet. Chem., 2015, 29, 1-6.
[http://dx.doi.org/10.1002/aoc.3234]
[41]
Gholinejad, M.; Shahsavari, H.R. Inorganica Chim Acta, 2014, 421, 433-438.https://doi.org/https://doi.org/10.1016/j.ica.2014.06.039
[42]
Xu, Q.; Duan, W-L.; Lei, Z-Y. Tetrahedron, 2005, 61, 11225-11229.
[http://dx.doi.org/10.1016/j.tet.2005.09.010]
[43]
Chen, T.; Gao, J.; Shi, M. Tetrahedron, 2006, 62, 6289-6294.
[http://dx.doi.org/10.1016/j.tet.2006.04.034]
[44]
Nasrollahzadeh, M.; Azarian, A.; Maham, M.; Ehsani, A. J. Ind. Eng. Chem., 2015, 21, 746-748.
[http://dx.doi.org/10.1016/j.jiec.2014.04.006]
[45]
Nasrollahzadeh, M.; Sajadi, S.M.; Maham, M. J. Mol. Catal. Chem., 2015, 396, 297-303.
[http://dx.doi.org/10.1016/j.molcata.2014.10.019]
[46]
Faria, V.W.; Oliveira, D.G.M.; Kurz, M.H.S. RSC Advances, 2014, 4, 13446-13452.
[http://dx.doi.org/10.1039/C4RA01104J]
[47]
Islam, S.M.; Roy, A.S.; Mondal, P.; Salam, N. Appl. Organomet. Chem., 2012, 26, 625-634.
[http://dx.doi.org/10.1002/aoc.2911]
[48]
Yılmaz Baran, N.; Baran, T.; Menteş, A. Carbohydr. Polym., 2018, 181, 596-604.
[http://dx.doi.org/10.1016/j.carbpol.2017.11.107] [PMID: 29254012]
[49]
Baran, T. Ultrason. Sonochem., 2018, 45, 231-237.
[http://dx.doi.org/10.1016/j.ultsonch.2018.03.017] [PMID: 29705317]
[50]
Khalili, D.; Banazadeh, A.R.; Etemadi-Davan, E. Catal. Lett., 2017, 147, 2674-2687.
[http://dx.doi.org/10.1007/s10562-017-2150-1]
[51]
Ansari, R.M.; Bhat, B.R. J. Chem. Sci., 2017, 129, 1483-1490.
[http://dx.doi.org/10.1007/s12039-017-1347-6]
[52]
Tahmasbi, B.; Ghorbani-Choghamarani, A. Catal. Lett., 2017, 147, 649-662.
[http://dx.doi.org/10.1007/s10562-016-1927-y]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy