Abstract
The paper describes synthesis of a novel mesoporous and magnetically regenerated heterogeneous nanocatalyst with high catalytic activity. The synthesis strategy includes a one-step polycondensation reaction of melamine, formaldehyde and FeCl3·6H2O in a simple and sustainable manner and followed by immobilization of Pd(II) on it. Formation and properties of nanocomposite were characterized by different techniques; the results were illustrated good surface area and a well-defined mesopore structure. Also the palladium-catalyzed C–C bond formation between aryl halides and olefins was selected to survey the activity of the synthesized nanocatalyst. Central Composite Design (CCD) strategy was used to predict the optimum synthesis conditions and identify the remarkable and effective factors including temperature, period of the reaction and amount of catalyst. These results were also verified experimentally. In order to minimize systematic error, the experimental runs as a randomized fashion were accomplished.
Similar content being viewed by others
References
Y. Zhang, S.N. Riduan, Chem. Soc. Rev. 41, 2083–2094 (2012)
P.M. Budd, B. Ghanem, K. Msayib, N.B. McKeown, C. Tattershall, J. Mater. Chem. 13, 2721–2726 (2003)
M.X. Tan, L. Gu, N. Li, J.Y. Ying, Y. Zhang, Green Chem. 15, 1127–1132 (2013)
D. Wu, F. Xu, B. Sun, R. Fu, H. He, K. Matyjaszewski, Chem. Rev. 112, 3959–4015 (2012)
J.-X. Jiang, F. Su, A. Trewin, C.D. Wood, H. Niu, J.T. Jones, Y.Z. Khimyak, A.I. Cooper, J. Am. Chem. Soc. 130, 7710–7720 (2008)
J.-X. Jiang, A.I. Cooper, Functional metal-organic frameworks: gas storage, Separation and Catalysis (Springer, Berlin, 2009), pp. 1–33
A. Thomas, Angew. Chem. Int. Ed. 49, 8328–8344 (2010)
N.B. McKeown, P.M. Budd, Chem. Soc. Rev. 35, 675–683 (2006)
N.B. McKeown, J. Mater. Chem. 20, 10588–10597 (2010)
A. Stein, Adv. Mater. 15, 763–775 (2003)
L. Pan, Q. He, J. Liu, Y. Chen, M. Ma, L. Zhang, J. Shi, J. Am. Chem. Soc. 134, 5722–5725 (2012)
W. Lu, D. Yuan, J. Sculley, D. Zhao, R. Krishna, H.-C. Zhou, J. Am. Chem. Soc. 133, 18126–18129 (2011)
M.X. Tan, Y.N. Sum, J.Y. Ying, Y. Zhang, Energ Environ. Sci. 6, 3254–3259 (2013)
M.B. Steffensen, E. Hollink, F. Kuschel, M. Bauer, E.E. Simanek, J. Polym. Sci. A 44, 3411–3433 (2006)
T.J. Mooibroek, P. Gamez, Inorg. Chim. Acta 360, 381–404 (2007)
G.M. Ziarani, Z. Hassanzadeh, P. Gholamzadeh, S. Asadi, A. Badiei, RSC Adv. 6, 21979–22006 (2016)
D. Huang, G. Yang, X. Feng, X. Lai, P. Zhao, New J. Chem. 39, 4685–4694 (2015)
A. Saad, C. Vard, M. Abderrabba, M.M. Chehimi, Langmuir 33, 7137–7146 (2017)
Z. Michalska, B. Ostaszewski, J. Zientarska, B. Kolarz, M. Wojaczyńska, React. Polym. 16, 213–221 (1992)
C.M. Park, M.S. Kwon, J. Park, Synthesis 2006, 3790–3794 (2006)
X. Ma, T. Jiang, B. Han, J. Zhang, S. Miao, K. Ding, G. An, Y. Xie, Y. Zhou, A. Zhu, Catal. Commun. 9, 70–74 (2008)
M. Lim, K.A. De Castro, S. Oh, K. Lee, Y.W. Chang, H. Kim, H. Rhee, Appl. Organomet. Chem. 25, 1–8 (2011)
M. Tian, C. Dong, X. Cui, Z. Dong, RSC Adv. 6, 99114–99119 (2016)
C.C. JohanssonSeechurn, M.O. Kitching, T.J. Colacot, V. Snieckus, Angew. Chem. Int. Ed. 51, 5062–5085 (2012)
X. Min, M.W. Kanan, J. Am. Chem. Soc. 137, 4701–4708 (2015)
Y.-F. Jiang, C.-Z. Yuan, X. Xie, X. Zhou, N. Jiang, X. Wang, M. Imran, A.-W. Xu, ACS Appl. Mater. Interfaces. 9, 9756–9762 (2017)
M.R. Nabid, Y. Bide, S.J.T. Rezaei, Appl. Catal. A 406, 124–132 (2011)
Y. Xu, L. Zhang, Y. Cui, J. Appl. Polym. Sci. 110, 2996–3000 (2008)
F. Zhen, M. Ran, W. Chu, C. Jiang, W. Sun, Chem. Phys. Lett. 695, 183–189 (2018)
A.K. Sutar, Y. Das, S. Pattnaik, A. Routaray, N. Nath, P. Rath, T. Maharana, Chin. J. Catal. 35, 1701–1708 (2014)
Y.-B. Zhou, Y.-Q. Wang, L.-C. Ning, Z.-C. Ding, W.-L. Wang, C.-K. Ding, R.-H. Li, J.-J. Chen, X. Lu, Y.-J. Ding, J. Am. Chem. Soc. 139, 3966–3969 (2017)
A. Suzuki, Chem. Soc. Rev. 40, 5010–5029 (2011)
J.-M. Gaudin, Tetrahedron Lett. 32, 6113–6116 (1991)
L.E. Overman, D.J. Ricca, V.D. Tran, J. Am. Chem. Soc. 115, 2042–2044 (1993)
L.F. Tietze, W. Buhr, Angew. Chem. Int. Ed. 34, 1366–1368 (1995)
R.R. Bader, P. Baumeister, H.-U. Blaser, Chimia 50, 99–105 (1996)
A. Zapf, M. Beller, Top. Catal. 19, 101–109 (2002)
C. Torborg, M. Beller, Adv. Synth. Catal. 351, 3027–3043 (2009)
G. Zou, W. Huang, Y. Xiao, J. Tang, New J. Chem. 30, 803–809 (2006)
J. Li, Q. Li, L.-S. Li, L. Xu, Chem. Eng. J. 320, 501–509 (2017)
Y. Song, R. Ma, C. Jiao, L. Hao, C. Wang, Q. Wu, Z. Wang, Microchim. Acta 185, 19 (2018)
X. Wang, J. Wang, C. Jiao, L. Hao, Q. Wu, C. Wang, Z. Wang, Talanta 179, 676–684 (2018)
R.A. Molla, M.A. Iqubal, K. Ghosh, A.S. Roy, S.M. Islam, RSC Adv. 4, 48177–48190 (2014)
S. Brunauer, L.S. Deming, W.E. Deming, E. Teller, J. Am. Chem. Soc. 62, 1723–1732 (1940)
R. Akkaya, U. Ulusoy, J. Hazard. Mater. 151, 380–388 (2008)
W. Wang, A. Wang, Carbohydr. Polym. 77, 891–897 (2009)
A. Banazadeh, A. Pirisedigh, F. Aryanasab, H. Salimi, S. Shafiei-Haghighi, Inorg. Chim. Acta 429, 132–137 (2015)
R.N. Baig, J. Leazer, R.S. Varma, Clean Technol. Environ. 17, 2073–2077 (2015)
K. Bahrami, M.M. Khodaei, F.S. Meibodi, Appl. Organomet. Chem. 31, e3627 (2017)
S.J. Tabatabaei Rezaei, A. Shamseddin, A. Ramazani, A. Mashhadi Malekzadeh, P. Azimzadeh Asiabi, Appl. Organomet. Chem. 31, e3707 (2017)
S. Kumari, S. Layek, D.D. Pathak, New J. Chem. 41, 5595–5604 (2017)
A. Ghorbani-Choghamarani, B. Tahmasbi, N. Noori, R. Ghafouri-nejad, J. Iran. Chem. Soc. 14, 681–693 (2017)
A. Ghorbani-Choghamarani, M. Norouzi, New J. Chem. 40, 6299–6307 (2016)
M. Nikoorazm, A. Ghorbani-Choghamarani, N. Noori, B. Tahmasbi, Appl. Organomet. Chem. 30, 843–851 (2016)
Y. Li, L. Xu, B. Xu, Z. Mao, H. Xu, Y. Zhong, L. Zhang, B. Wang, X. Sui, ACS Appl. Mater. Interfaces. 9, 17155–17162 (2017)
Y. Rangraz, F. Nemati, A. Elhampour, New J. Chem. 42, 15361–15371 (2018)
V. Somjit, M. Wong Chi Man, A. Ouali, P. Sangtrirutnugul and V. Ervithayasuporn, ChemistrySelect 3, 753-759 (2018)
R.J. Kalbasi, M. Negahdari, J. Mol. Struct. 1063, 259–268 (2014)
N. Arsalani, A. Akbari, M. Amini, E. Jabbari, S. Gautam, K.H. Chae, Catal. Lett. 147, 1086–1094 (2017)
Acknowledgements
The authors gratefully acknowledge the Semnan University Research Council for the financial support of this work.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Shahamat, Z., Nemati, F. & Elhampour, A. Palladium (II) anchored on a magnetic mesoporous polymelamine–formaldehyde as new catalyst for Heck coupling reaction: optimization of reaction using response surface methodology. J Porous Mater 27, 107–122 (2020). https://doi.org/10.1007/s10934-019-00795-x
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10934-019-00795-x