Synthesis and characterization of a Pd (0) Schiff base complex anchored on magnetic nanoporous MCM-41 as a novel and recyclable catalyst for the Suzuki and Heck reactions under green conditions

Abstract

Abstract:

A Pd Schiff base complex was immobilized onto the surface of magnetic MCM-41 (Fe₃O₄@MCM-41@Pd(0)-P2C) as a novel, eco-friendly, and recyclable heterogeneous nanocatalyst and fully characterized by FT-IR, VSM, EDS, transmission electron microscopy, scanning electron microscopy, thermogravimetric analyses, ICP-OES, and X-ray powder diffraction analysis. The Fe₃O₄@MCM-41@Pd(0)-P2C was investigated as a catalyst for the one-pot Suzuki and Heck reactions in PEG as a green solvent to provide the target products in excellent yields. The main advantages of using this catalyst include a short reaction time, green reaction conditions, a simple experimental procedure, non-use of hazardous organic solvents, low loading of the catalyst, and the ability to use various substrates. More importantly, the catalyst could be easily separated from the reaction mixture with the assistance of an external magnet and could be recovered and reused several times without significant loss of stability and activity.

Key words: MCM-41, Magnetic nanoparticles, Suzuki reaction, Heck reaction, Polyethylene glycol (PEG), Palladium

Mohsen Nikoorazm, Farshid Ghorbani, Arash Ghorbani-Choghamarani, Zahra Erfani. Synthesis and characterization of a Pd (0) Schiff base complex anchored on magnetic nanoporous MCM-41 as a novel and recyclable catalyst for the Suzuki and Heck reactions under green conditions[J]. Chinese Journal of Catalysis, 2017, 38(8): 1413-1422.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/

https://www.cjcatal.com/EN/Y2017/V38/I8/1413

References

[1] S. Rostamizadeh, M. Nojavan, R. Aryan, E. Isapoor, M. Azad, J. Mol. Catal. A, 2013, 374, 102-110.
[2] M. Nikoorazm, A. Ghorbani-Choghamarani, H. Mahdavi, S. M. Esmaeili, Microporous Mesoporous Mater., 2015, 211, 174-181.
[3] S. V. Kolotilov, O. Shvets, O. Cador, N. Kasian, V. G. Pavlov, L. Oua-hab, V. G. Ilyin, V. V. Pavlishchuk, J. Solid State Chem., 2006, 179, 2426-2432.
[4] M. Hasanzadeh, N. Shadjou, E. Omidinia, Colloids Surf. B, 2013, 108, 52-59.
[5] M. Nikoorazm, A. Ghorbani-Choghamarani, F. Ghorbani, H. Mahdavi, Z. Karamshahi, J. Porous Mater., 2015, 22, 261-267.
[6] F. B. Zanardi, I. A. Barbosa, P. C. de Sousa Filho, L. D. Zanatta, D. L. da Silva, O. A. Serra, Y. Iamamoto, Microporous Mesoporous Mater., 2016, 219, 161-171.
[7] A. Jabbari, H. Mahdavi, M. Nikoorazm, A. Ghorbani-Choghamarani, Res. Chem. Intermed., 2015, 41, 5649-5663.
[8] N. Noori, M. Nikoorazm, A. Ghorbani-Choghamarani, J. Porous. Mater., 2016, 23, 1467-1481.
[9] M. Nikoorazm, A. Ghorbani-Choghamaran, N. Noori, J. Porous Mater., 2015, 22, 877-885.
[10] M. Abdollahi-Alibeik, A. Rezaeipoor-Anari, J. Magn. Magn. Mater., 2016, 398, 205-214.
[11] S. Rostamizadeh, N. Zekri, Res. Chem. Intermed., 2016, 42, 2329-2341.
[12] M. Arruebo, W. Y. Ho, K. F. Lam, X. Q. Chen, J. Arbiol, J. Santamaria, K. L. Yeung, Chem. Mater., 2008, 20, 486-493.
[13] Z. Abbasi, S. Rezayati, M. Bagheri, R. Hajinasiri, Chin. Chem. Lett., 2017, 28, 75-82.
[14] A. Ghorbani-Choghamarani, G. Azadi, RSC Adv., 2015, 5, 9752-9758.
[15] A. Ghorbani-Choghamarani, M. Norouzi, J. Mol. Catal. A, 2014, 395, 172-179.
[16] M. Hasanzadeh, M. H. Pournaghi-Azar, N. Shadjou, A. Jouyban, RSC Adv., 2014, 4, 4710-4717.
[17] A. Ghorbani-Choghamarani, B. Tahmasbi, P. Moradi, RSC Adv., 2016, 6, 43205-43216.
[18] H. P. Fan, Z. L. Qi, D. J. Sui, F. Mao, R. Z. Chen, J. Huang, Chin. J. Catal., 2017, 38, 589-596.
[19] B. Luo, J. Q. Wang, D. H. Ge, X. M. Li, X. Q. Cao, Y. Pan, H. W. Gu, Sci. China Chem., 2014, 57, 1310-1314.
[20] A. Ghorbani-Choghamarani, B. Tahmasbi, P. Moradi, Appl. Organomet. Chem., 2016, 30, 422-430.
[21] Q. Sun, L. F. Zhu, Z. H. Sun, X. J. Meng, F. S. Xiao, Sci. China Chem., 2012, 55, 2095-2103.
[22] L. Zhou, W. D. Zhang, H. F. Jiang, Sci. China Chem., 2008, 51, 241-257.
[23] H. Chen, P. Zhang, W. H. Tan, F. Jiang, R. Tang, RSC Adv., 2014, 4, 38743-38749.
[24] M. Nikoorazm, A. Ghorbani-Choghamarani, N. Noori. Res. Chem. Intermed., 2016, 42, 4621-4640.
[25] A. Ghorbani-Choghamarani, Z. Darvishnejad, B. Tahmasbi, Inorg. Chim. Acta., 2015, 435, 223-231.
[26] F. B. Zanardi, I. A. Barbosa, P. C. de Sousa Filho, L. D. Eabatta, D. L. dasilva, O. A. Serra, Microporous Mesoporous Mater., 2016, 219, 161-171.
[27] S. Rostamizadeh, M. Nojavan, R. Aryan, M. Azad, Catal. Lett., 2014, 144, 1772-1783.
[28] A. Ghorbani-Choghamarani, H. Rabiei, Tetrahedron Lett., 2016, 57, 159-162.
[29] Y. Y. Peng, J. B. Liu, X. L. Lei, Z. L. Yin, Green Chem., 2010, 12, 1072-1075
[30] M. Samarasimharseddy, G. Prabhu, T. M. Vishwanatha, V. V. Sureshbabu, Synthesis, 2013, 45, 1201-1206.
[31] N. S. C. Ramesh Kumar, I. Victor Paul Raj, A. Sudalai, J. Mol. Catal. A, 2007, 269, 218-224.
[32] Q. Xu, W. L. Duan, Z. Y. Lei, Z. B. Zhu, M. Shi, Tetrahedron, 2005, 61, 11225-11229.
[33] N. Iranpoor, H. Firouzabadi, A. Tarassoli, M. Fereidoonnezhad, Tetrahedron, 2010, 66, 2415-2421.
[34] A. Naghipour, A. Fakhri, Catal. Commun., 2016, 73, 39-45.
[35] Y. T. Leng, F. Yang, K. Wei, Y. J. Wu, Tetrahedron, 2010, 66, 1244-1248.
[36] L. Wang, H. J. Li, P. H. Li, Tetrahedron, 2009, 65, 364-368.
[37] S. Sobhani, Z. M. Falatooni, S. Asadi, M. Honarmand, Catal. Lett., 2016, 146, 255-268.
[38] S. Sobhani, M. S. Ghasemzadeh, M. Honarmand, F. Zarifi, RSC Adv., 2014, 83, 44166-44174.
[39] M. Nikoorazm, A. Ghorbani-Choghamarani, A. Jabbari, J. Porous Mater., 2016, 23, 967-975.
[40] S. Singha, M. Sahoo, K. M. Parida, Dalton Trans., 2011, 40, 7130-7132.
[41] M. Z. Cai, Q. H. Xu, Y. X. Huang, J. Mol. Catal. A, 2007, 271, 93-97.
[42] S. Sobhani, Z. Zeraatkar, F. Zarifi, New. J. Chem., 2015, 39, 7076-7085.
[43] Y. Q. Zhang, X. W. Wei, R. Yu, Catal. Lett., 2010, 135, 256-262.
[44] M. Nasrollahzadeh, S. M. Sajadi, M. Maham, J. Mol. Catal. A, 2015, 396, 297-303.
[45] Q. Xu, W. L. Duan, Z. Y. Lei, Z. B. Zhu, M. Shi, Tetrahedron, 2005, 61, 11225-11229.
[46] M. Esmaeilpour, J. Javidi, J. Chin. Chem. Soc., 2015, 62, 614-626.
[47] D. S. Gaikwad, Y. K. Park, D. M. Pore, Tetrahedron Lett., 2012, 53, 3077-3081.
[48] F. W. Zhang, J. R. Niu, H. B. Wang, H. L. Yang, J. Jin, N. Liu, Y. B. Zhang, R. Li, J. T. Ma, Mater. Res. Bull., 2012, 47, 504-507.
[49] A. E. Wang, J. H. Xie, L. X. Wang, Q. L. Zhou, Tetrahedron, 2005, 61, 259-266.
[50] H. Veisi, A. Sedrpoushan, S. Hemmati, Appl. Organomet. Chem., 2015, 12, 825-828.
[51] T. Chen, J. Gao, M. Shia, Tetrahedron, 2006, 62, 6289-6294.
[52] Q. Zhang, X. Zhao, H. X. Wei, J. H. Li, J. Luo, Appl. Organomet. Chem., 2016, doi:10.1002/aoc.3608.
[53] S. Sobhani, F. Zarifi, Chin. J. Catal., 2015, 36, 555-563.
[54] P. H. Li, L. Wang, L. Zhang, G. W. Wang, Adv. Synth. Catal., 2012, 354, 1307-1318.