Abstract
A simple and efficient method for phosphine-free C–C coupling reactions such as Heck and Suzuki reactions in the presence of pyrrole Schiff base complex of palladium immobilized on mesoporous mesoporous of MCM-41 (Pd-Py-MCM-41) has been reported. The Suzuki reaction was carried out in PEG-400 using phenylboronic acid (PhB(OH)2). Pd-Py-MCM-41 has been found as a promising catalyst for Heck reaction of butyl acrylate with aryl halides (including Cl, Br and I). The catalyst was characterized by FT-IR, TEM, XRD, SEM, BET and ICP-OES techniques. The protocol proves to be efficient and environmentally benign in terms of high yield, easy of recovery and reusability of catalyst.
Similar content being viewed by others
References
S. Pasa, Y.S. Ocak, H. Temel, T. Kilicoglu, Inorg. Chim. Acta 405, 493 (2013)
S. Nadri, M. Joshaghani, E. Rafiee, Appl. Catal. A Gen. 362, 163 (2009)
A.R. Hajipour, F. Raiee, J. Iran. Chem. Soc. 12, 1177 (2015)
P.M. Uberman, L.A. Perez, S.E. Martın, G.I. Lacconi, RSC Adv. 4, 12330 (2014)
G. Herve, G. Sartori, G. Enderlin, G. Mackenzie, C. Len, RSC Adv. 4, 18558 (2014)
V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.M. Basset, Chem. Rev. 111, 3036 (2011)
A. Rostami, B. Tahmasbi, A. Yari, Bull. Korean Chem. Soc. 34, 1521 (2013)
A. Ghorbani-Choghamarani, B. Tahmasbi, F. Arghand, S. Faryadi, RSC Adv. 5, 92174 (2015)
Y. Zhu, L.P. Stubbs, F. Ho, R. Liu, C.P. Ship, J.A. Maguire, N.S. Hosmane, Chemcatchem. 2, 365 (2010)
C.W. Lim, I.S. Lee, Nano Today 5, 412 (2010)
S. Shylesh, V. Schunemann, W.R. Thiel, Angew. Chem. Int. Ed. 49, 3428 (2010)
M. Hajjami, B. Tahmasbi, RSC Adv. 5, 59194 (2015)
M. Abdollahi-Alibeik, M. Pouriayevali, Catal. Commun. 22, 13 (2012)
M. Nikoorazm, A. Ghorbani-Choghamarani, F. Ghorbani, H. Mahdavi, Z. Karamshahi, J. Porous Mater. 22, 261 (2015)
M. Nikoorazm, A. Ghorbani-Choghamarani, N. Noori, Appl. Organomet. Chem. 29, 328 (2015)
S.A. Idris, S.R. Harvey, L.T. Gibson, J. Hazard. Mater. 193, 171 (2011)
G. Maria, A.I. Stoica, I. Luta, D. Stirbet, G.L. Radu, Micro. Mesog. Mater. 162, 80 (2012)
A. Benhamou, J.P. Basly, M. Baudu, Z. Derriche, R. Hamacha, J. Colloid Interface Sci. 404, 135 (2013)
S. Yan, L. Xiu-Wu, S. Wei, Z. Yaping, Z. Li, Appl. Surf. Sci. 253, 5650 (2007)
A. Ghorbani-Choghamarani, F. Nikpour, F. Ghorbani, F. Havasi, RSC Adv. 5, 33212 (2015)
Y. Huang, W. Hao, G. Ding, M.Z. Cai, J. Organomet. Chem. 715, 141 (2012)
N. Cuello, V. Elías, M. Crivello, M. Oliva, G. Eimer, J. Solid State Chem. 205, 91 (2013)
M. Nikoorazm, A. Ghorbani-Choghamarani, N. Noori, J. Porous Mater. 22, 877 (2015)
A. Ghorbani-Choghamarani, Z. Darvishnejad, B. Tahmasbi, Inorg. Chim. Acta 435, 223 (2015)
Y.Y. Peng, J. Liu, X. Lei, Z. Yin, Green Chem. 12, 1072 (2010)
L. Baia, J.X. Wanga, Adv. Synth. Catal. 350, 315 (2007)
T. Chen, J. Gao, M. Shi, Tetrahedron 62, 6289 (2006)
N. Iranpoor, H. Firouzabadi, A. Tarassoli, M. Fereidoonnezhad, Tetrahedron 66, 2415 (2010)
X. Le, Z. Dong, Z. Jin, Q. Wang, J. Ma, Catal. Commun. 53, 47 (2014)
M. Nasrollahzadeh, S.M. Sajadi, M. Maham, J. Mol. Catal. A: Chem. 396, 297 (2015)
V.W. Faria, D.G.M. Oliveira, M.H.S. Kurz, F.F. Goncalves, C.W. Scheeren, G.R. Rosa, RSC Adv. 4, 13446 (2014)
M. Nasrollahzadeh, A. Azarian, M. Maham, A. Ehsani, J. Ind. Eng. Chem. 21, 746 (2015)
A. Modak, J. Mondal, M. Sasidharan, A. Bhaumik, Green Chem. 13, 1317 (2011)
S. Singha, M. Sahoo, K.M. Parida, Dalton Trans. 40, 7130 (2011)
H.A. Patel, A.L. Patel, A.V. Bedekar, Appl. Organomet. Chem. 29, 1 (2015)
M. Hajjami, F. Ghorbani, F. Bakhti, Appl. Catal. A Gen. 470, 303 (2014)
Acknowledgments
This work was supported by the research facilities of Ilam University, Ilam, Iran.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Nikoorazm, M., Ghorbani-Choghamarani, A. & Jabbari, A. A facile preparation of palladium Schiff base complex supported into MCM-41 mesoporous and its catalytic application in Suzuki and Heck reactions. J Porous Mater 23, 967–975 (2016). https://doi.org/10.1007/s10934-016-0154-7
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10934-016-0154-7