A comparative study between Cu(INA)₂-MOF and [Cu(INA)₂(H₂O)₄] complex for a click reaction and the Biginelli reaction under solvent-free conditions

Abstract

The catalytic application of Cu(INA)2-MOF in click and Biginelli reactions was investigated and a comparative study with the [Cu(INA)2(H2O)4] complex was performed.

Topologically Driven Pore/Surface Engineering in a Recyclable Microporous Metal–Organic Vessel Decorated with Hydrogen-Bond Acceptors for Solvent-Free Heterogeneous Catalysis

“…Compared to the MOFs reported in the literature, wherein most of the catalytic active sites are Lewis acidic in nature, the efficiency of catalyst 1 is noteworthy (Table S2), specifically the temperature of the reaction. As mentioned earlier, most of the reaction conditions require either reflux conditions or heating at a temperature of 80 °C. − Other MOFs containing unsaturated Lewis acidic metal sites (Zn­(II), Cd­(II), or Cu­(II)), which lower the reaction temperature to ∼50–60 °C, require a high catalyst loading of up to 10 mol %. − In contrast to these examples, catalyst 1 effectively catalyzes the Biginelli reaction at 35 °C at a relatively low catalyst loading of 2 mol %. This may be probably due to the lowering of the transition-state energy required to bring the multicomponents involved in the Biginelli reaction close to each other, which is otherwise ensured by an increase in the reaction temperature.…”

“…Other strategies involving polymer-supported catalysts might still require the use of strong acids and expensive reagents and result in environmental pollution . Moreover, in most of the cases, the reaction requires high temperatures (80 °C or above in most cases) − and yields low conversion percentages (of only up to 25%) if the reaction temperature is decreased …”

“…29 Moreover, in most of the cases, the reaction requires high temperatures (80 °C or above in most cases) 30−38 and yields low conversion percentages (of only up to 25%) if the reaction temperature is decreased. 33 On the basis of the above difficulties, we aimed at synthesizing a bifunctional, nontoxic, recyclable microporous 3D MOF catalyst for the multicomponent Biginelli reaction, wherein the objective was to decrease the transition state of the system not only by activating the electrophilic aldehydic center but also by bringing the multicomponents in close proximity to each other. In addition to affording a Lewis acid catalytic site through the unsaturated metal site in the MOF, we focused on a linker design with H-bond acceptors in an oxadiazole moiety and its consequent tendency to dock the urea molecules involved in the catalysis; oxadiazole moieties are known for their H-bond-acceptor properties due to the nonligand electron pairs from the heteroatom present in their structure.…”

MOF-Derived Cu@N-C Catalyst for 1,3-Dipolar Cycloaddition Reaction

“…Metal-organic frameworks (MOFs), an essential class of porous materials composed of metal/metal clusters and polydentate organic ligands, have also been targeted as excellent heterogeneous catalyst [ 23 , 24 , 25 , 26 ] or catalyst supports [ 27 ] for the preparation of various 1,2,3-triazoles, regarding their elevated surface areas, tunable porous structures, and easy synthetic procedure. However, some of them are inevitably unstable in organic/water or pure water solvents due to the higher affinities of metal ions with water molecules than the organic ligands, causing the damage of MOFs structures [ 28 ].…”

Fe3O4@MCM‐41@ZrCl2: A novel magnetic mesoporous nanocomposite catalyst including zirconium nanoparticles for the synthesis of 1‐(benzothiazolylamino)phenylmethyl‐2‐naphthols

“…In spite of significant advances in the field of mesoporous materials and the growing expansion of new types of them, [1][2][3][4][5][6][7][8] the first and foremost member of M41S called MCM-41 still has attracted growing research attention owing to its chemical versatility. [9][10][11][12][13] Its capabilities, especially in the field of catalytic activity, all come from its unique properties, such as high surface area ($1000 m 2 g −1 ), narrow pore size distribution, uniform pore size, and the possibility of adjusting the diameter of the pores between 2 and 10 nm.…”