Hybridization of NH2-MIL-88B/Deep eutectic solvent: A novel multifunctional heterogeneous catalyst for the synthesis of spirooxindoles. / Askari, Saeed; Khodaei, Mohammad Mehdi; Benassi, Enrico et al.
In: Journal of Molecular Liquids, Vol. 387, 122646, 01.10.2023.Research output: Contribution to journal › Article › peer-review
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TY - JOUR
T1 - Hybridization of NH2-MIL-88B/Deep eutectic solvent: A novel multifunctional heterogeneous catalyst for the synthesis of spirooxindoles
AU - Askari, Saeed
AU - Khodaei, Mohammad Mehdi
AU - Benassi, Enrico
AU - Jafarzadeh, Mohammad
N1 - Funding: This study was funded by Razi University with no grant number.
PY - 2023/10/1
Y1 - 2023/10/1
N2 - Deep eutectic solvents (DESs) with outstanding environmental suitability have emerged as green alternatives to ionic liquids (ILs) and many other organic solvents. Nevertheless, their separation from reaction media and reuse is still problematic. Hence, the heterogenization of DESs on proper support can overcome their drawbacks. Herein, a DES-supported catalyst was prepared for the synthesis of organic compounds. Initially, the surface of Fe-based MOF, NH2–MIL-88B, was modified via a polymerization reaction between MOF amino groups, cyanuric chloride, and urea. Then, choline chloride (ChCl) was stabilized on the surface of modified MOF, NH2–MIL-88B-CU, through hydrogen bonding. NH2–MIL-88B-CU@ChCl as a multifunctional catalyst (Brønsted/Lewis acids and Brønsted base), with alluring attributes like environmental sustainability, chemical and thermal stability, retrievability, and reusability, was used for the one-pot three-component synthesis of spirooxindoles. Its high catalytic performance was related to a synergistic effect between active sites of NH2–MIL-88B-CU and ChCl. NH2–MIL-88B not only provided a platform for immobilizing of DESs but also showed catalytic activity through Fe-oxo nodes. Quantum chemical calculations were performed to shed light on the reaction mechanism. In addition, green metrics parameters have shown that the present method is more efficient than some reported homogeneous and heterogeneous catalytic systems while providing less waste, which is vital from the viewpoint of green chemistry. The hot filtration test and the retrievability/reusability of the catalyst proved the structural stability and heterogeneous nature of the hybrid system.
AB - Deep eutectic solvents (DESs) with outstanding environmental suitability have emerged as green alternatives to ionic liquids (ILs) and many other organic solvents. Nevertheless, their separation from reaction media and reuse is still problematic. Hence, the heterogenization of DESs on proper support can overcome their drawbacks. Herein, a DES-supported catalyst was prepared for the synthesis of organic compounds. Initially, the surface of Fe-based MOF, NH2–MIL-88B, was modified via a polymerization reaction between MOF amino groups, cyanuric chloride, and urea. Then, choline chloride (ChCl) was stabilized on the surface of modified MOF, NH2–MIL-88B-CU, through hydrogen bonding. NH2–MIL-88B-CU@ChCl as a multifunctional catalyst (Brønsted/Lewis acids and Brønsted base), with alluring attributes like environmental sustainability, chemical and thermal stability, retrievability, and reusability, was used for the one-pot three-component synthesis of spirooxindoles. Its high catalytic performance was related to a synergistic effect between active sites of NH2–MIL-88B-CU and ChCl. NH2–MIL-88B not only provided a platform for immobilizing of DESs but also showed catalytic activity through Fe-oxo nodes. Quantum chemical calculations were performed to shed light on the reaction mechanism. In addition, green metrics parameters have shown that the present method is more efficient than some reported homogeneous and heterogeneous catalytic systems while providing less waste, which is vital from the viewpoint of green chemistry. The hot filtration test and the retrievability/reusability of the catalyst proved the structural stability and heterogeneous nature of the hybrid system.
KW - DFT
KW - Deep-eutectic solvent
KW - Metal-organic frameworks
KW - NH2–MIL-88B
KW - Spirooxindoles
UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85166736926&origin=inward&txGid=725f915e6ee5fb84480724498ff24bc8
UR - https://www.mendeley.com/catalogue/599f1a7f-4bf1-3ce7-87b7-10fa667d72cb/
U2 - 10.1016/j.molliq.2023.122646
DO - 10.1016/j.molliq.2023.122646
M3 - Article
VL - 387
JO - Journal of Molecular Liquids
JF - Journal of Molecular Liquids
SN - 0167-7322
M1 - 122646
ER -
ID: 53967756