Brønsted-Lewis dual acid sites in a chromium-based metal-organic framework for cooperative catalysis: Highly efficient synthesis of quinazolin-(4H)-1-one derivatives

Oudi, Sara; Oveisi, Ali Reza; Daliran, Saba; Khajeh, Mostafa; Teymoori, Elias

doi:10.1016/j.jcis.2019.11.056

Cited by 42 publications

(14 citation statements)

References 86 publications

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“…This process can be done by either the direct use of organic linkers with functional groups or postsynthetic modification (PSM). Several reports have indicated the valuable role of the functionalization of MOFs with the −NO 2 group in various applications, such as catalytic activity, , CO 2 adsorption, and enzyme mimic activity (Table ). The presence of the polar group in the structure of MOFs with the ability to make interactions with guest molecules (such as hydrogen bonding) could improve the potential of MOFs for better performances in different applications, including drug delivery .…”

Section: Introductionmentioning

confidence: 99%

Two-Fold Homointerpenetrated Metal–Organic Framework with the Potential for Anticancer Drug Loading Using Computational Simulations

Alavijeh

Akhbari

Tylianakis

et al. 2021

Crystal Growth & Design

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A new 2-fold homointerpenetrated metal–organic framework with one-dimensional helical channels along [100] direction with the formula {[Zn(NO2-BDC)]·DMF} n (MUT-2) was synthesized and characterized by single-crystal X-ray crystallography. This MOF with NO2-decorated channels was obtained from the self-assembly of 2-nitroterephthalic acid (NO2-H2BDC) as the organic ligand and Zn(NO3)2·6H2O as metallic nodes. The structural properties of the MOF were estimated theoretically by computational simulations. In addition, the potential of MUT-2 for drug loading, i.e. 5-FU as an anticancer drug molecule model, was evaluated computationally. The results were compared with those for MOF-123, which has also been studied for the same purpose, and MUT-2 performed better than MOF-123. The obtained results show a higher surface area (1250 m2/g), larger free volume (60%), and better drug loading (841 mg/g) for MUT-2 in comparison with MOF-123 with 1120 m2/g surface area, 47% free volume, and 453.9 mg/g drug loading.

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Section: Introductionmentioning

confidence: 99%

Two-Fold Homointerpenetrated Metal–Organic Framework with the Potential for Anticancer Drug Loading Using Computational Simulations

Alavijeh

Akhbari

Tylianakis

et al. 2021

Crystal Growth & Design

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“…Metal–organic frameworks (MOFs), prepared from the self-assembly of metal clusters/ions and organic ligands, have attracted remarkable research interest in catalysis, gas separation, sensing, and so forth. − MOFs possess many advantages such as large surface area, well-defined structure, and available functionalization, − and they have been an intriguing class of heterogeneous catalytic materials for a diverse range of organic transformations. − Among various MOFs reported, MIL-101 (Matérial Institut Lavoisier) with two kinds of mesoporous cages (3.4 and 2.9 nm, respectively) and high thermal and chemical stability has been a striking material for catalysis. − The water molecules coordinated on the chromium clusters can be eliminated upon heating in vacuum, which generates coordinatively unsaturated Cr sites that can work as Lewis acid sites for catalysis. − Very recently, Garcia et al reported that MIL-101(Cr) with abundant Cr sites catalyzes the benzylic autoxidation of indane . A mechanism study revealed that MIL-101(Cr) acts as a radical initiator in the autoxidation of benzylic C–H with molecular oxygen as the oxidizing agent.…”

Section: Introductionmentioning

confidence: 99%

Cooperative Interplay of Brønsted Acid and Lewis Acid Sites in MIL-101(Cr) for Cross-Dehydrogenative Coupling of C–H Bonds

Chen

Zhang

Chen

et al. 2021

ACS Appl. Mater. Interfaces

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Cross-dehydrogenative coupling (CDC) is an effective tool for carbon–carbon bond formation in chemical synthesis. Herein, we report a metal–organic framework (MOF) possessing dual Lewis acidic Cr sites and sulfonic acid sites (MIL-101(Cr)–SO3H) as an efficient catalytic material for direct cross-coupling of xanthene and different nucleophiles using O2 as the oxidant. The highly porous structure of MIL-101(Cr)–SO3H enables the free access of reactants to the catalytic active sites inside MOF pores. Kinetic studies indicated that the Cr sites of MOF accelerate the rate-limiting autoxidation reaction of xanthene, which synergistically work with the sulfonic acid group on MOF ligands in promoting the CDC reactions. Besides, the catalytic system shows excellent functional group compatibility, and a variety of valuable xanthene derivatives were synthesized with satisfactory yields. Furthermore, MIL-101(Cr)–SO3H can be reused and its catalytic activity and crystal structure remain after six consecutive runs.

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“…[19,21] Thus, to overcome this drawback, some Brønsted acidic molecules or groups are introduced into MOFs via encapsulation [22][23][24] or post-modification. [25][26][27] In 2011, Kitagawa's group successfully functionalized MIL-101(Cr) with sulfonic groups (MIL-101(Cr)-SO 3 H) and found that sulfonic groups in the pores enormously improved the catalytic activity of MIL-101(Cr) for the cellulose hydrolysis reaction. [28] In this respect, MIL-101(Cr)-SO 3 H has started to arouse much interest.…”

Section: S C H E M E 1 Bioactive Compounds Containing Tetrahydroquinoline Structural Fragmentsmentioning

confidence: 99%

Heterogeneous synthesis of tetrahydroquinoline derivatives via cascade Povarov reaction catalyzed by sulfonic acid functionalized metal‐organic frameworks

et al. 2021

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We report a facile synthesis of tetrahydroquinoline derivatives via heterogeneous cascade Povarov reaction catalyzed by sulfonic acid functionalized metal-organic frameworks (MIL-101(Cr)-SO 3 H). The porous MIL-101(Cr)-SO 3 H demonstrates superior catalytic activities and stabilities for this reaction in comparison either to homogeneous sulfonic acids or heterogeneous sulfonic acid resins. Experimental investigations reveal that the high catalytic performance is attributed to the cooperative action of dual Lewis-and Brønsted acid sites within the pores of MIL-101(Cr)-SO 3 H. In addition, this reaction proceeds smoothly at room temperature with a broad substrate scope, which provides an alternative approach in the construction of tetrahydroquinoline skeletons. K E Y W O R D S heterogeneous catalysis, MIL-101(Cr)-SO 3 H, povarov reaction, tetrahydroquinolineThis is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

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Brønsted-Lewis dual acid sites in a chromium-based metal-organic framework for cooperative catalysis: Highly efficient synthesis of quinazolin-(4H)-1-one derivatives

Cited by 42 publications

References 86 publications

Two-Fold Homointerpenetrated Metal–Organic Framework with the Potential for Anticancer Drug Loading Using Computational Simulations

Two-Fold Homointerpenetrated Metal–Organic Framework with the Potential for Anticancer Drug Loading Using Computational Simulations

Cooperative Interplay of Brønsted Acid and Lewis Acid Sites in MIL-101(Cr) for Cross-Dehydrogenative Coupling of C–H Bonds

Heterogeneous synthesis of tetrahydroquinoline derivatives via cascade Povarov reaction catalyzed by sulfonic acid functionalized metal‐organic frameworks

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