Abstract
A simple and efficient procedure was reported for the synthesis of tetrazole derivatives, the chemo and homoselective oxidation of sulfides to sulfoxides in the presence of two Schiff-base complexes of zirconium oxide and copper anchored on MCM-41 as mesoporous and organometallic catalysts under green conditions. All the products were obtained in excellent yields with high TOF values indicating the high activity of the synthesized catalysts. These catalysts were characterized by XRD, TGA, SEM, EDS, FT-IR, TEM, WDX, BET and AAS techniques and can be recycled for several times without significant loss in catalytic activity. The recovered catalysts were characterized by SEM, FT-IR and AAS analysis which shown an excellent agreement with fresh catalysts.
Similar content being viewed by others
References
J. Govan, K.Y. Gunko, Nanomaterials 4, 222 (2014)
T. Baran, N. Yılmaz Baran, A. Menteş, Appl. Organomet. Chem. 32, e4075 (2018)
T. Baran, Ultrason. Sonochem. 45, 231 (2018)
D. Wang, D. Astruc, Chem. Rev. 114, 6949 (2014)
S. Shylesh, V. Schünemann, W.R. Thiel, Angew. Chem. Int. Ed. 49, 3428 (2010)
R.R. Langeslay, D.M. Kaphan, C.L. Marshall, P.C. Stair, A.P. Sattelberger, M. Delferro, Chem. Rev. 119, 2128 (2019)
T. Baran, N. Yılmaz Baran, A. Menteş, J. Mol. Struct. 1160, 154 (2018)
P. Ju, S. Wu, Q. Su, X. Li, Z. Liu, G. Li, Q. Wu, J. Mater. Chem. A 7, 2660 (2019)
T. Baran, Carbohydr. Polym. 195, 45 (2018)
Y. Rangraz, F. Nemati, A. Elhampour, New J. Chem. 42, 15361 (2018)
A. Ghorbani-Choghamarani, M. Hajjami, B. Tahmasbi, N. Noori, J. Iran. Chem. Soc. 13, 2193 (2016)
J.K. Anjali, K. Sreekumar, Catal. Lett. 149, 1952 (2019)
V. Polshettiwar, R.S. Varma, Green Chem. 12, 743 (2010)
T. Baran, N. Yılmaz Baran, A. Menteş, Int. J. Biol. Macromol. 115, 249 (2018)
D. Ma, Y. Wang, A. Liu, S. Li, C. Lu, C. Chen, Catalysts 8, 404 (2018)
M. Nikoorazm, A. Ghorbani-Choghamarani, A. Panahi, B. Tahmasbi, N. Noori, J. Iran. Chem. Soc. 15, 181 (2018)
C.W. Lim, I.S. Lee, Nano Today 5, 412 (2010)
V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.-M. Basset, Chem. Rev. 111, 3036 (2011)
A. Ghorbani-Choghamarani, B. Tahmasbi, R.H.E. Hudson, A. Heidari, Microporous Mesoporous Mater. 284, 366 (2019)
B. Karimi, M. Tavakolian, F. Mansouri, H. Vali, A.C.S. Sustain, Chem. Eng. 7, 3811 (2019)
E. Gross, F. Dean Toste, G.A. Somorjai, Catal. Lett. 145, 126 (2015)
B. Tahmasbi, A. Ghorbani-Choghamarani, Catal. Lett. 147, 649 (2017)
H. Veisi, A. Nikseresht, N. Ahmadi, K. Khosravi, F. Saeidifar, Polyhedron 162, 240 (2019)
Z.B. Shifrina, V.G. Matveeva, L.M. Bronstein, Chem. Rev. (2019). https://doi.org/10.1021/acs.chemrev.9b00137
S.Y. Chong, T.T. Wang, L.C. Cheng, H.Y. Lv, M. Ji, Langmuir 35, 495 (2019)
T.T. Nguyen, X.-T.T. Nguyen, T.-L.H. Nguyen, P.H. Tran, ACS Omega 4, 368 (2019)
A. Ghorbani-Choghamarani, B. Tahmasbi, N. Noori, S. Faryadi, Comptes Rendus Chim. 20, 132 (2017)
R.M. Ansari, B.R. Bhat, Chem. Phys. 517, 155 (2019)
V.B. Saptal, M.V. Saptal, R.S. Mane, T. Sasaki, B.M. Bhanage, ACS Omega 4, 643 (2019)
A. Ghorbani-Choghamarani, M. Nikoorazm, H. Goudarziafshar, B. Tahmasbi, Bull. Korean Chem. Soc. 40, 1388 (2009). https://doi.org/10.1002/chin.200945034
B. Tahmasbi, A. Ghorbani-Choghamarani, Appl. Organomet. Chem. 31, e3644 (2017)
K. Bahrami, M. Khodamorady, Catal. Lett. 149, 688 (2019)
S.A. Idris, S.R. Harvey, L.T. Gibson, J. Hazard. Mater. 193, 171 (2011)
M. Nikoorazm, N. Noori, B. Tahmasbi, S. Faryadi, Transit. Met. Chem. 42, 469 (2017)
G. Maria, A.-I. Stoica, I. Luta, D. Stirbet, G.L. Radu, Microporous Mesoporous Mater. 162, 80 (2012)
Y. Sun, X.-W. Liu, W. Su, Y. Zhou, L. Zhou, Appl. Surf. Sci. 253, 5650 (2007)
A. Benhamou, J.P. Basly, M. Baudu, Z. Derriche, R. Hamacha, J. Colloid Interface Sci. 404, 135 (2013)
M. Nikoorazm, A. Ghorbani-Choghamarani, N. Noori, B. Tahmasbi, Appl. Organomet. Chem. 30, 843 (2016)
M. Nikoorazm, A. Ghorbani-Choghamarani, F. Ghorbani, H. Mahdavi, Z. Karamshahi, J. Porous Mater. 22, 261 (2015)
M. Abdollahi-Alibeik, M. Pouriayevali, Catal. Commun. 22, 13 (2012)
Y. Huang, W. Hao, G. Ding, M.-Z. Cai, J. Organomet. Chem. 715, 141 (2012)
S. Rojas-Buzo, P. García-García, A. Corma, Catal. Sci. Technol. 9, 146 (2019)
N. Yan, C. You, M. Cai, J. Organomet. Chem. 897, 161 (2019)
H. Veisi, T. Tamoradi, B. Karmakar, New J. Chem. 43, 10343 (2019)
M. Bharathi, S. Indira, G. Vinoth, K. Shanmuga Bharathi, J. Porous Mater. 26, 1377 (2019)
S. Molaei, M. Ghadermazi, Appl. Organomet. Chem. 33, e4854 (2019)
M. Nikoorazm, A. Ghorbani-Choghamaranai, M. Khanmoradi, P. Moradi, J. Porous Mater. 25, 1831 (2018)
A. Ghorbani-Choghamarani, P. Moradi, B. Tahmasbi, Polyhedron 163, 98 (2019)
T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, Catal. Lett. 148, 857 (2018)
T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, New J. Chem. 42, 5479 (2018)
A. Ghorbani-Choghamarani, P. Moradi, B. Tahmasbi, RSC Adv. 6, 56638 (2016)
A. Ghorbani-Choghamarani, P. Moradi, B. Tahmasbi, RSC Adv. 6, 56458 (2016)
A. Ghorbani-Choghamarani, P. Moradi, B. Tahmasbi, J. Iran. Chem. Soc. 16, 511 (2019). https://doi.org/10.1007/s13738-018-1526-5
A. Ghorbani-Choghamarani, H. Goudarziafshar, M. Nikoorazm, S. Yousefi, Lett. Org. Chem. 6, 335 (2009)
M. Safaiee, M. Moeinimehr, M.A. Zolfigol, Polyhedron 170, 138 (2019)
M. Zolfigol, F. Shirini, A. Choghamarani, Synthesis (Stuttg). 2006, 2043 (2006)
G. Chehardoli, M.A. Zolfigol, Phosphorus, Sulfur Silicon Relat. Elem. 185, 193 (2010)
K. Amani, M.A. Zolfigol, A. Ghorbani-Choghamarani, M. Hajjami, Monat. Chem. Chem. Mon. 140, 65 (2009)
A. Hasaninejad, G. Chehardoli, M.A. Zolfigol, A. Abdoli, Phosphorus Sulfur Silicon Relat. Elem. 186, 271 (2011)
M.A. Zolfigol, K. Amani, A. Ghorbani-Choghamarani, M. Hajjami, R. Ayazi-Nasrabadi, S. Jafari, Catal. Commun. 9, 1739 (2008)
T. Baran, E. Açıksöz, A. Menteş, J. Mol. Catal. A: Chem. 407, 47 (2015)
B. Tahmasbi, A. Ghorbani-Choghamarani, New J. Chem. 43, 14485 (2019)
A. Ghorbani-Choghamarani, H. Rabiei, B. Tahmasbi, B. Ghasemi, F. Mardi, Res. Chem. Intermed. 42, 5723 (2016). https://doi.org/10.1007/s11164-015-2399
S.M. Islam, A.S. Roy, P. Mondal, K. Tuhina, M. Mobarak, J. Mondal, Tetrahedron Lett. 53, 127 (2012)
A. Ghorbani-Choghamarani, B. Tahmasbi, P. Moradi, N. Havasi, Appl. Organomet. Chem. 30, 619 (2016)
M. Nikoorazm, A. Ghorbani-Choghamarani, H. Mahdavi, S.M. Esmaeili, Microporous Mesoporous Mater. 211, 174 (2015)
S. Hussain, D. Talukdar, S.K. Bharadwaj, M.K. Chaudhuri, Tetrahedron Lett. 53, 6512 (2012)
C. Yu, C.-X. Guo, C.-L. Zhong, Z.-F. Diao, L.-N. He, Tetrahedron Lett. 55, 1818 (2014)
M.A. Zolfigol, A. Khazaei, M. Safaiee, M. Mokhlesi, R. Rostamian, M. Bagheri, M. Shiri, H.G. Kruger, J. Mol. Catal. A: Chem. 370, 80 (2013)
Y. Hu, W. Ma, M. Tao, X. Zhang, X. Wang, X. Wang, L. Chen, J. Appl. Polym. Sci. 135, 46036 (2018)
M. Nikoorazm, M. Ghobadi, Silicon 11, 983 (2019)
D. Habibi, M.A. Zolfigol, M. Safaiee, A. Shamsian, A. Ghorbani-Choghamarani, Catal. Commun. 10, 1257 (2009)
Acknowledgements
This work was supported by the research facilities of Ilam University, Ilam, Iran.
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.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Nikoorazm, M., Rezaei, Z. & Tahmasbi, B. Two Schiff-base complexes of copper and zirconium oxide supported on mesoporous MCM-41 as an organic–inorganic hybrid catalysts in the chemo and homoselective oxidation of sulfides and synthesis of tetrazoles. J Porous Mater 27, 671–689 (2020). https://doi.org/10.1007/s10934-019-00835-6
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10934-019-00835-6