Three-Component Coupling of Aldehyde, Alkyne, and Amine via C–H Bond Activation Using Indium-Based Metal–Organic Framework Mil-68(In) as a Recyclable Heterogeneous Catalyst

Metal-organic frameworks (MOFs) are ac lass of crystalline porousm aterials that have been activelyu sed for several industrial and synthetica pplications.M OFs are spatially and geometrically extrapolatedc oordination polymers with intriguing properties such as tunable porosity and dimensionality.Int erms of their catalytic efficiency,MOFs combine the easy recoverability of heterogeneous catalysts with the increased selectivity of biological catalysts. It is therefore not surprising that alot of work on optimizing MOF catalysts for organic transformationsh as been carriedo ut over the past decade. In this review,recent developments in MOF catalysis are summarized, with special attention being paid to CÀC, CÀN, and CÀOc oupling reactions. The influence of pore size, pore environment, and load on catalytic activity is described. Post-synthetics tabilization techniques and hostguest interactions in caged MOF scaffolds are detailed. Mechanistic aspects pertaining to the use of MOFs in asymmetric heterogeneousc atalysis are highlighted and categorized.

show abstract

“…Lam et al [188] synthesized an indium-containing MOF MIL-68 for catalyzing three-componentc oupling reactions. The MOF Figure 54.…”

Section: Lanthanides and Heavy Metalsmentioning

confidence: 99%

Engineering Metal–Organic Framework Catalysts for C−C and C−X Coupling Reactions: Advances in Reticular Approaches from 2014–2018

Kousik

Velmathi

2019

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…The metal‐catalyzed coupling reaction of aldehydes, amines, and alkynes (A 3 coupling) to give propargyl amines has been improved in recent years. [ 18–20 ] The only by‐product is water in this method, which is a one‐pot multicomponent reaction. Most biomedical studies on silver–NHC complexes have been conducted concerning their antimicrobial properties.…”

Section: Introductionmentioning

confidence: 99%

Silver–N‐heterocyclic carbene complexes‐catalyzed multicomponent reactions: Synthesis, spectroscopic characterization, density functional theory calculations, and antibacterial study

Mnasri

Mejri

Al-Hazmy

et al. 2021

Archiv der Pharmazie

View full text Add to dashboard Cite

Nowadays, silver–N‐heterocyclic carbene (silver–NHCs) complexes are widely used in medicinal chemistry due to their low toxic nature toward humans. Due to the success of silver–NHCs in medicinal applications, interest in these compounds is rapidly increasing. Therefore, the interaction of N,N‐disubstituted benzimidazolium salts with Ag2O in dichloromethane to prepare novel Ag(I)–NHCs complexes was carried out at room temperature for 120 h in the absence of light. The obtained complexes were identified and characterized by 1H and 13C nuclear magnetic resonance, Fourier‐transform infrared, UV–Vis, and elemental analysis techniques. Then, the silver complexes were applied for three‐component coupling reactions of aldehydes, amines, and alkynes. The effect of changing the alkyl substituent on the NHCs ligand on the catalytic performance was investigated. In addition, it has been found that the complexes are antimicrobially active and show higher activity than the free ligand. The silver–carbene complexes showed antimicrobial activity against specified microorganisms with MIC values between 0.24 and 62.5 μg/ml. These results showed that the silver–NHC complexes exhibit an effective antimicrobial activity against bacterial and fungal strains. A density functional theory calculation study was performed to identify the stability of the obtained complexes. All geometries were optimized employing an effective core potential basis, such as LANL2DZ for the Ag atom and 6‐311+G(d,p) for all the other atoms in the gas phase. Electrostatic potential surfaces and LUMO–HOMO energy were computed. Transition energies and excited‐state structures were obtained from the time‐dependent density functional theory calculations.

show abstract

“…11 Meanwhile, ZIFs possess zeolite topology in which divalent metal cations are linked to a tetrahedral framework by imidazole acid anions, resulting in a large surface area and pore volume and unique inherent biodegradability. 12−14 So far, ZIF-8 has been widely used in catalytic magnetic separation, 15 magnetic resonance, 16 drug delivery, 17−19 imaging, 20 and other areas, but there are few reports on the adsorption of fluorescent probes. Now, people use two-dimensional materials as biosensors to conduct systematic and in-depth research on the detection of fluorescent DNA.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Zeolitic imidazolate frameworks (ZIFs) are important branches of MOFs, which is a new type of nanoporous material with zeolite topology formed by linking transition metal atoms (Zn) with imidazole or imidazole derivatives. − Compared with zeolite, transition metal ions replace silicon and aluminum in traditional zeolites, and imidazole esters replace oxygen bridges in traditional zeolites . Meanwhile, ZIFs possess zeolite topology in which divalent metal cations are linked to a tetrahedral framework by imidazole acid anions, resulting in a large surface area and pore volume and unique inherent biodegradability. − So far, ZIF-8 has been widely used in catalytic magnetic separation, magnetic resonance, drug delivery, − imaging, and other areas, but there are few reports on the adsorption of fluorescent probes.…”

Section: Introductionmentioning

confidence: 99%

Investigating Adsorption/Desorption of DNA on ZIF-8 Surface by Fluorescently Labeled Oligonucleotides

et al. 2019

View full text Add to dashboard Cite

As an important subclass of MOFs, ZIF-8, built from 2-methylimidazole and Zn(NO3)2·6H2O, possesses excellent biocompatibility and high stability in aqueous solution. Recently, it has been found that ZIF-8 can efficiently adsorb DNA and quench the adsorbed fluorophores to a large extent. These properties make it possible to prepare DNA-based optical sensors using ZIF-8. Although practical analytical applications are being demonstrated, the basic understanding of the binding between ZIF-8 and DNA in solution has received relatively little attention. In this work, we report that the adsorption of 12-, 18-, 24-, and 36-mer single-stranded DNAs on ZIF-8 are affected by several factors. It is found from the outcomes that shorter DNAs are adsorbed more rapidly to the surface of ZIF-8. On the other hand, desorption of the probe DNA can be achieved using complementary strand DNA to restore the fluorescence value. Furthermore, the salt contributes to adsorption to some extent. These findings are important for further understanding of the interactions between DNA and ZIF-8 and for the optimization of DNA and MOF-based devices and sensors.

show abstract

Three-Component Coupling of Aldehyde, Alkyne, and Amine via C–H Bond Activation Using Indium-Based Metal–Organic Framework Mil-68(In) as a Recyclable Heterogeneous Catalyst

Cited by 12 publications

References 61 publications

Engineering Metal–Organic Framework Catalysts for C−C and C−X Coupling Reactions: Advances in Reticular Approaches from 2014–2018

Engineering Metal–Organic Framework Catalysts for C−C and C−X Coupling Reactions: Advances in Reticular Approaches from 2014–2018

Silver–N‐heterocyclic carbene complexes‐catalyzed multicomponent reactions: Synthesis, spectroscopic characterization, density functional theory calculations, and antibacterial study

Investigating Adsorption/Desorption of DNA on ZIF-8 Surface by Fluorescently Labeled Oligonucleotides

Contact Info

Product

Resources

About