Abstract
The surface of the MCM-41 has been functionalized with 3-chloropropyltrimethoxysilane, which undergoes an SN2 substitution reaction of the chloro group with the nitrogen of ligand (quinoline-2-4-dicarboxylic acid), offering the MCM-41-quinoline-2-4-dicarboxylic acid (MCM-41-QDC’s). A new recyclable Ni attached functionalized mesoporous MCM-41 (MCM-41-QDC’s-Ni) has been produced through a post-synthetic method. This catalyst displays high catalytic performance in the synthesis of 5-substituted 1H-tetrazoles and the selective oxidation of sulfides. This protocol is a greener way toward the synthesis of 5-substituted 1H-tetrazoles and the selective oxidation of sulfides. The main aspects of this economical Ni-catalyzed procedure are green synthesis, slighter experimental conditions, and lesser reaction time with no additives. Further benefits comprise experimental comfort of handling, securer replacement to dangerous, damaging, and poisoning regular Lewis’s acid catalysts. The catalyst can be simply separated by simple recovery and reused for several periods without any remarkable decrease in the catalyst activity and selectivity.
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References
B.A. Keay, P.W. Dibble, A.R. Katritzky, C.W. Rees, E.F.V. Scriven, A.R. Katritzky, Comprehensive heterocyclic chemistry II (Elsevier, Netherlands, 1996), pp. 395–436
R.J. Herr, Bioorg. Med. Chem. 10, 3379–3393 (2002)
N.A. Meanwell, J. Med. Chem. 54, 2529–2591 (2011)
M.A. Malik, M.Y. Wani, S.A. Al-Thabaiti, R.A. Shiekh, J Incl Phenom Macrocycl Chem. 78, 15–37 (2014)
R. Mittal, S.K. Awasthi, Synthesis 51, 3765–3783 (2019)
R.S. Varma, K.P. Naicker, Org. Lett. 1, 189–192 (1999)
Y. Imada, H. Iida, S. Ono, S.-I. Murahashi, J. Am. Chem. Soc. 125, 2868–2869 (2003)
B. Kotelanski, R.J. Grozmann, J.N. Cohn, Clin. Pharmacol. Ther. 14, 427–433 (1973)
M. Sovova, P. Sova, Ceska. Slov. Farm. 52, 82–87 (2003)
G. Merino, A.J. Molina, J.L. Garcia, M.M. Pulido, J.G. Prieto, A.I. Alvarez, J. Pharm. Pharmacol. 55, 757–764 (2003)
G.W. Gokel, H.M. Gerdes, D.M. Dishong, J. Org. Chem. 45, 3634–3639 (1980)
J.M. Khurana, A.K. Panda, A. Ray, A. Gogia, Org. Prep. Proced. Int. 28, 234–237 (1996)
N.J. Leonard, C.R. Johnson, J. Org. Chem. 27, 282–284 (1962)
K. Kaczorowska, Z. Kolarska, K. Mitka, P. Kowalski, Tetrahedron 35, 8315–8327 (2005)
S. Rostamnia, B. Gholipour, X. Liu, Y. Wang, H. Arandiyan, J. Colloid Interface Sci. 511, 447–455 (2018)
R. Maggi, S. Chitsaz, S. Loebbecke, C.G. Piscopo, G. Sartori, M. Schwarzer, Green Chem. 13, 1121–1123 (2011)
N. Moeini, T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, Appl. Organomet. Chem. 32, e4445 (2018)
L. Shiri, A. Ghorbani-Choghamarani, M. Kazemi, Res. Chem. Intermed. 43, 2707–2724 (2017)
T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, S. Molaei, Res. Chem. Intermed. 44, 4259–4276 (2018)
S. Molaei, M. Ghadermazi, Solid State Sci. 101, 106148 (2020)
S. Molaei, M. Ghadermazi, Appl. Organomet. Chem. 34, e5328 (2020)
S. Molaei, M. Ghadermazi, Solid State Sci. 100, 106091 (2020)
S. Rostamnia, T. Rahmani, Appl. Organomet. Chem. 29, 471–474 (2015)
S. Rostamnia, E. Doustkhah, J. Mol. Catal. Chem. 411, 317–324 (2016)
E. Doustkhah, S. Rostamnia, H.G. Hossieni, R. Luque, ChemistrySelect 2, 329–334 (2017)
S. Molaei, M. Ghadermazi, Appl. Organomet. Chem. 33, e4972 (2019)
S. Molaei, M. Ghadermazi, Appl. Organomet. Chem. 33, e4854 (2019)
S. Molaei, M. Ghadermazi, Micropor. Mesopor. Mat. 319, 110990 (2021)
S. Molaei, T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, Appl. Organomet. Chem. 33, e4649 (2019)
S. Molaei, T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, Polyhedron 156, 35–47 (2018)
S. Molaei, T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, Micropor. Mesopor. Mat. 272, 241–250 (2018)
S. Rostamnia, X. Liu, D. Zheng, J. Colloid Interface Sci. 432, 86–91 (2014)
S. Molaei, T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, Catal. Lett. 148, 1834–1847 (2018)
K. Ma, C. Bi, X. Zhang, Z. Zong, C. Fan, C. Xu, Y.H. Fan, Inorganica Chim. Acta. 494, 91–97 (2019)
X. Xue, Y. Liu, Y. Xing, X. Wang, W. Li, J Inorg Organomet Polym Mater. 28, 820–828 (2018)
J.N. Appaturi, M.R. Johan, R.J. Ramalingam, H.A. Al-Lohedan, Micropor. Mesopor. Mat. 256, 67–74 (2018)
I. Ibrahim, S. Yunus, M. Hashim, J. sci. Eng. Res. 4, 1–12 (2013)
M. Kim, S. Hwang, J.-S. Yu, J. Mater. Chem. 17, 1656–1659 (2007)
S. Jana, B. Dutta, R. Bera, S. Koner, Langmuir 23, 2492–2496 (2007)
S. Bhunia, D. Saha, S. Koner, Langmuir 27, 15322–15329 (2011)
Y.-M. Liu, J. Xu, L. He, Y. Cao, H.-Y. He, D.-Y. Zhao, J.-H. Zhuang, K.-N. Fan, J. Phys. Chem. C. 112, 16575–16583 (2008)
Y.M. Wang, Z.Y. Wu, L.Y. Shi, J.H. Zhu, Adv. Mater. 17, 323–327 (2005)
S.M. Rivera-Jiménez, S. Méndez-González, A. Hernández-Maldonado, Micropor. Mesopor. Mat. 132, 470–479 (2010)
M. Khanmoradi, M. Nikoorazm, A. Ghorbani-Choghamarani, Appl. Organomet. Chem. 31, e3693 (2017)
V. Rama, K. Kanagaraj, K. Pitchumani, J. Org. Chem. 76, 9090–9095 (2011)
R. Das, D. Chakraborty, Tetrahedron Lett. 51, 6255–6258 (2010)
A. Ghorbani-Choghamarani, P. Moradi, B. Tahmasbi, RSC Adv. 6, 56458–56466 (2016)
A.M.I. Jayaseeli, S. Rajagopal, J. Mol. Catal. Chem. 309, 103–110 (2009)
A.M.I. Jayaseeli, A. Ramdass, S. Rajagopal, Polyhedron 100, 59–66 (2015)
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The authors are deeply grateful to the University of Kurdistan for the financial support this research project.
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Molaei, S., Ghadermazi, M. Introduction of Ni into mesoporous MCM-41: A new recyclable catalyst for the synthesis of 5-substituted 1H-tetrazoles and the selective oxidation of sulfides. J Porous Mater 29, 1929–1945 (2022). https://doi.org/10.1007/s10934-022-01270-w
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DOI: https://doi.org/10.1007/s10934-022-01270-w