Palladium Loaded on Magnetic Nanoparticles as Efficient and Recyclable Catalyst for the Suzuki- Miyaura Reaction

Document Type : Research Paper

Authors

Department of Chemistry, Catalysis Division, University of Isfahan, Isfahan.

10.7508/jns.2015.03.009

Abstract

Palladium is the best metal catalyst for Suzuki cross coupling reaction for synthesize of unsymmetrical biaryl compounds. But its high cost limits its application in wide scale. Using of nanoscale particles as active catalytic cites is a good approach for reducing needed noble metal. By loading precious nanoparticles on magnetic nanocores as a support, recycling and reusing of catalyst will be possible. Magnetic nanoparticles have super paramagnetic feature and applying an external magnetic field can collect the supported catalyst from reaction milieu simply. In this work new palladium catalyst immobilized on modified magnetic nanoparticles containing NNO donor atoms were synthesized. Then the catalyst characterized by FT-IR spectroscopy, thermogravimetric analysis, X-ray diffraction and ICP. Prepared catalyst showed high activity in the Suzuki– Miyaura cross-coupling reaction of phenylboronic acid with aryl halides. Activity, Pd loading, reusability and Pd leaching of catalyst were studied. Results showed that the supported catalyst has the advantage to be completely recoverable with the simple application of an external magnetic field.

Keywords

References

[1] J.H. Clark, D.J. MacQuarrie, J.H. Clark, D.J. MacQuarrie, Handbook of Green Chemistry & Technology, Blackwell, Oxford, 2002.
[2] P.T. Anastas, M.M. Kirchhoff, T.C. Williamson, Applied Catalysis A: General 221 (2001) 3-13.
[3] S. Miao, C. Zhang, Z. Liu, B. Han, Y. Xie, S. Ding, Z. Yang, The Journal of Physical Chemistry C 112 (2008) 774-780.
[4] C.W. Lim, I.S. Lee, Nano Today 5 (2010) 412-434.
[5] A. Fihri, M. Bouhrara, B. Nekoueishahraki, J.-M. Basset, V. Polshettiwar, Chem Soc Rev. 40 (2011) 5181-5203.
[6] G.R. Bardajee, R. Malakooti, I. Abtin, H. Atashin, Microporous and Mesoporous Materials 169 (2013) 67-74.
[7] D. Astruc, F. Lu, J.R. Aranzaes, Angew Chem Int Ed Engl, 44 (2005) 7852-7872.
[8] S. Paul, J.H. Clark, Green Chemistry 5 (2003) 635-638.
[9] K.C. Nicolaou, E.J. Sorensen, Wiley-VCH, Weinheim1996.
[10] Á. Molnár, Chemical Reviews 111 (2011) 2251-2320.
[11] R. Narayanan, Molecules 15 (2010) 2124.
[12] A. Fihri, M. Bouhrara, B. Nekoueishahraki, J.-M. Basset, V. Polshettiwar, Chem Soc Rev 40 (2011) 5181-5203.
[13] N. Miyaura, A. Suzuki, Chemical Reviews 95 (1995) 2457-2483.
[14] Y. He, C. Cai, Catalysis Communications 12 (2011) 678-683.
[15] F. Bellina, A. Carpita, R. Rossi, Synthesis 15 (2004) 2419-2440.
[16] N.T.S. Phan, C.S. Gill, J.V. Nguyen, Z.J. Zhang, C.W. Jones, Angewandte Chemie International Edition 45 (2006) 2209-2212.
[17] J.-P. Corbet, G. Mignani, Chemical Reviews 106 (2006) 2651-2710.
[18] J. Wu, P. Su, J. Huang, S. Wang, Y. Yang, J Colloid Interface Sci 399 (2013) 107-114.
[19] B. Tamami, H. Allahyari, S. Ghasemi, F. Farjadian, Journal of Organometallic Chemistry 696 (2011) 594-599.
[20] N.T.S. Phan, H.V. Le, Journal of Molecular Catalysis A: Chemical 334 (2011) 130-138.
[21] P. Das, D. Sharma, A.K. Shil, A. Kumari, Tetrahedron Letters 52 (2011) 1176-1178.
[22] N.T. Bui, T.B. Dang, H.V. Le, N.T.S. Phan, Chinese Journal of Catalysis 32 (2011) 1667-1676.
[23] P. Wang, Q. Lu, J. Li, Materials Research Bulletin 45 (2010) 129-134.
[24] G. Fan, B. Zou, S. Cheng, L. Zheng, Journal of Industrial and Engineering Chemistry 16 (2010) 220-223.
[25] M. Kooti, M. Afshari, Catal Lett
 142 (2012) 319-325.
[26] S. Paul, J.H. Clark, Journal of Molecular Catalysis A: Chemical 215 (2004) 107-111.
[27] N.T.S. Phan, C.W. Jones, Journal of Molecular Catalysis A: Chemical 253 (2006) 123-131.
[28] Y. W, M.S. M, PanZ, O.S. H, D. S, Journal of the American Chemical Society 127 (2005) 10480-10481.
[29] D. Astruc, F. Lu, J.R. Aranzaes, Angew Chem Int Ed Engl 44 (2005) 7852-7872.
[30] C.W. Lim, I.S. Lee, Nano Today 5 (2010) 412-434.
[31] N.T.S. Phan, C.S. Gill, J.V. Nguyen, Z.J. Zhang, C.W. Jones, Angewandte Chemie International Edition 45 (2006) 2209-2212.
[32] N.J.S. Costa, P.K. Kiyohara, A.L. Monteiro, Y. Coppel, K. Philippot, L.M. Ross, Journal of Catalysis 276 (2010) 382-389.
[33] V.M. Nosova, Y.A. Ustynyuk, L.G. Bruk, O.N. Temkin, A.V. Kisin, P.A. Storozhenko, Inorg Chem 50 (2011) 9300-9310.
 

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