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Heterogeneous Fe3O4@Si–NHC–Pd Catalyst: Synthesis, Characterization, and Catalytic Activity in the Suzuki–Miyaura Cross-Coupling Reaction under Mild Conditions

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Abstract

A novel Fe3O4@Si–NHC–Pd catalyst with N-heterocyclic carbenes (NHCs) moiety as an alternative ligand to phosphines for metal complexes has been synthesized and characterized by various methods. Synthesis of metal nanoparticles has been accomplished without aggregation, and the prepared catalyst has been applied in theSuzuki–Miyaura cross-coupling reaction of boronic acids and aryl halides in water using Et3N as a base. The catalyst has demonstrated high efficiency at room temperature and can be easily removed from the reaction media using an external magnetic field and recycled at least five times without significant decrease of its activity.

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REFERENCES

  1. Attarad, A., Zafar, H., Zia, M., Haq, I.U., Phull, A.R., Sarfraz, A.J., and Hussain, A., Nano. Technol. Sci. Appl., 2016, vol. 9, p. 49. https://doi.org/10.2147/NSA.S99986

  2. Pachon, L.D. and Rothenberg, G., Appl. Organometal. Chem., 2008, vol. 22, p. 288. https://doi.org/10.1002/aoc.1382

  3. White, R.J., Luque, R., Budarin, V.L., Clark, J.H., and Macquarrie, D.J., Chem. Soc. Rev., 2009, vol. 38, p. 481. https://doi.org/10.1039/B802654H

  4. Glorius, F., N-Heterocyclic Carbenes in Transition Metal Catalysis, Berlin: Springer, 2007, pp. 1–50.

  5. Würtz, S., Glorius, F., Acc. Chem. Res. 2008, vol. 41, p. 1523. https://doi.org/10.1021/ar8000876

  6. Ernst, J.B., Muratsugu, S., Wang, F., Tada, M., and Glorius, F., J. Am. Chem. Soc., 2016, vol. 138, p. 10718. https://doi.org/10.1021/jacs.6b03821

    Article  CAS  PubMed  Google Scholar 

  7. Ferry, A.l., Schaepe, K., Tegeder, P., Richter, C., Chepiga, K.M., Ravoo, B.J., and Glorius, F., ACS. Catal., 2015, vol. 5, p. 5414. https://doi.org/10.1021/acscatal.5b01160

  8. Assen, E., Kantchev, B., Obrien, C.J., and Organ, M.G., Angew. Chem. Int. Ed., 2007, vol. 46, p. 2768. https://doi.org/10.1002/anie.200601663

    Article  CAS  Google Scholar 

  9. Würtz, S. and Glorius, F., Acc. Chem. Res., 2008, vol. 41, p. 1523. https://doi.org/10.1021/ar8000876

  10. Navarro, O. and Nolan, S.P., Synthesis, 2006, vol. 2, p. 366. https://doi.org/10.1055/s-2005-918497

    Article  CAS  Google Scholar 

  11. Scott, N.M. and Nolan, S.P., Eur. J. Inorg. Chem., 2005, vol. 10, p. 1815. https://doi.org/10.1002/ejic.200500030

  12. Crabtree, R.H., J. Organomet. Chem., 2005, vol. 690, p. 5451. https://doi.org/10.1016/j.jorganchem.2005.07.099

    Article  CAS  Google Scholar 

  13. Herrmann, W.A., Schttz, J., Frey, G.D., and Herdtweck, E., Organometallics, 2006, vol. 25, p. 2437. https://doi.org/10.1021/om0600801

    Article  CAS  Google Scholar 

  14. Wu, G., Liu, Y., Yang, Z., Jiang, T., Katakam, N., Rouh, H., Ma, L., Tang, Y., Ahmed, S., Rahman, A.U., Huang, H., Unruh, D., and Li, G., Nat. Sci. Rev., 2020, vol. 7, p. 588. https://doi.org/10.1093/nsr/nwz203

    Article  Google Scholar 

  15. Akkoc, S., Gok, Y., Ilhan, I.O., and Kayser, V., J. Org. Chem., 2016, vol. 12, p. 81. https://doi.org/10.3762/bjoc.12.9

    Article  CAS  Google Scholar 

  16. Kremzow, D., Seidel, G., Lehmann, C.W., and Furstner, A., Chem. Eur. J., 2005, vol. 11, p. 1833. https://doi.org/10.1002/chem.200400928

  17. Dastgir, S., Coleman, K.S., Cowley, A.R., and Green, M.L.H, Organometallics, 2006, vol. 25, p. 300. https://doi.org/10.1021/om050775m

    Article  CAS  Google Scholar 

  18. Azad, M., Rostamizadeh, S., Estiri, H., and Nouri, F., Appl. Organometal. Chem., 2019, vol. 33, p. 4952. https://doi.org/10.1002/aoc.4952

    Article  CAS  Google Scholar 

  19. Azad, M., Rostamizadeh, S., Nouri, F., Estiri, H., and Fadakar, Y., Material Lett., 2019, vol. 236, p. 757. https://doi.org/10.1016/j.matlet.2018.10.171

    Article  CAS  Google Scholar 

  20. Ghavidel kalishomi, R., Rostamizade, S., Nouri, F., and Khazaei, A., Heliyon, 2020, vol. 6, p. 4946. https://doi.org/10.1016/j.heliyon.2020.e04946

  21. Sasidharan, D., Aji, C.V., and Mathew, P., Polyhedron, 2019, vol. 157, p. 335. https://doi.org/10.1016/j.poly.2018.10.022

    Article  CAS  Google Scholar 

  22. Kilic, A., Gezer, E., Durap, F., Aydemir, M., and Baysal, A., J. Organomet. Chem., 2019, vol. 896, p. 129. https://doi.org/10.1016/j.jorganchem.2019.06.007

    Article  CAS  Google Scholar 

  23. Zhang, Q., Su, H., Luo, J., and Wei, Y., Catal. Sci. Technol., 2013, vol. 3, p. 235. https://doi.org/10.1039/c2cy20532g

    Article  CAS  Google Scholar 

  24. Alavi Nikje, M.M., Ghavidel Kalishomi, R., and Akbar, R., Cellular Polymers, 2015, vol. 34, p. 249. https://doi.org/10.1177/026248931503400502

    Article  Google Scholar 

  25. Khaniani, Y., Badiei, A., and Mohammadi Ziarani, G., J. Mater. Res., 2012, vol. 27, p. 932. https://doi.org/10.1557/jmr.2011.435

  26. Kandathil, V., Kulkarni, B., Siddiqa, A., Kemoasiddalah, M., Sasidhar, B.S., Patil, S.A., and Patil, S.A., Catal. Lett., 2020, vol. 150, p. 484. https://doi.org/10.1007/s10562-019-03083-0

  27. Nouri, F., Rostamizadeh, S., and Azad, M., Mol. Catal., 2017, vol. 443, p. 286. https://doi.org/10.1016/j.mcat.2017.10.019

    Article  CAS  Google Scholar 

  28. Patil, S.A., Kandathil, V., Fahlman, B., and Patil, S.B.S., New. J. Chem., 2017, vol. 41, p. 9531. https://doi.org/10.1039/C7NJ01876Bhttps://doi.org/10.1007/s10562-019-03083-0

    Article  Google Scholar 

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ACKNOWLEDGMENTS

We gratefully appreciate the financial support from the Research Council of the K. N. Toosi University of Technology and Iran National Science Foundation.

Funding

This work was supported financially by K. N. Toosi University of Technology Research Council and Iran National Science Foundation (INSF).

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Correspondence to S. Rostamizadeh.

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Kalishomi, R.G., Rostamizadeh, S. Heterogeneous Fe3O4@Si–NHC–Pd Catalyst: Synthesis, Characterization, and Catalytic Activity in the Suzuki–Miyaura Cross-Coupling Reaction under Mild Conditions. Russ J Gen Chem 91, 1140–1146 (2021). https://doi.org/10.1134/S1070363221060244

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