Cu-Kojic Acid Complex Anchored to Functionalized Silica-MCM-41: A Promising Regioselective and Reusable Nanocatalyst for Click Reaction

Aghbash, Khadijeh Ojaghi; Pesyan, Nader Noroozi; Batmani, Hana

doi:10.1021/acsomega.0c02115

Cited by 11 publications

(8 citation statements)

References 49 publications

(63 reference statements)

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“…In our investigations into the use of new heterogeneous and reusable catalysts in organic converting, ,,− our decision was made to develop a new heterogeneous nanocatalyst (MCM-41-tryptophan-Zn) and apply it in the synthesis of 7-(phenyl(phenylamino)methyl)quoinolin-8-ol. The details of the method of preparing the catalyst are documented and presented by the short path given in Scheme .…”

Section: Resultsmentioning

confidence: 99%

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Zn Complex on Tryptophan-Functionalized MCM-41 as an Efficient and Promising Reusable Nanocatalyst in One-Pot Three-Component Synthesis of Amino Benzyl Quinolinols and Naphthols via a Betti Reaction

2023

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In this research, a Zn transition metallic complex on functionalized mesopore silica MCM-41 has been designed and utilized as an effective, recoverable, and thermally stable heterogeneous nanocatalyst in the formation of the C-C bond. Also, the synthesis of amino benzyl quinolinols and amino benzyl naphthol derivatives was performed by the three-component reaction of Betti from aromatic aldehydes, type II amines, and 8-hydroxyquinoline and 1-naphthol in the presence of the MCM-41tryptophan-Zn nanocatalyst under reflux conditions. The short reaction times, high efficiency of the products, the easy separation of catalysts due to their heterogeneity, and their reusability are the advantages of this method. Finally, the nature of catalysts was studied by using some techniques such as the Fourier transform infrared spectrum, energy-dispersive spectroscopy, hot filtration test, transmission electron microscopy, scanning electron microscopy, X-ray diffraction, inductively coupled plasma optical emission spectrometry, and N 2 adsorption-desorption (BET). The synthesized heterogeneous catalysts showed perfect catalytic activity and also good recyclability in the Betti reaction. They could be reused at least for five consecutive cycles without significant loss of their catalytic activities.

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Section: Resultsmentioning

confidence: 99%

“…MCM is a group of porous meso silicate compounds that are widely used due to their high surface area and high OH groups. They are utilized as surface adsorbents ion exchangers and various catalysts. − …”

Section: Introductionmentioning

confidence: 99%

Zn Complex on Tryptophan-Functionalized MCM-41 as an Efficient and Promising Reusable Nanocatalyst in One-Pot Three-Component Synthesis of Amino Benzyl Quinolinols and Naphthols via a Betti Reaction

2023

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“…The nanoporous MCM-41 was prepared with a sol–gel method according to our previous report 38 , 39 (Detailed in Support Information). Initially, 2.0 g calcinated MCM-41 was dissolved in 30 mL toluene solutions under the reflux condition at 12 h. Then, 10 mmol (2.4 mL) (3-chloropropyl) triethoxysilane was added to the mixture reaction under stir for 24 h. The prepared powder from the reaction was washed with ethanol several times, which obtain MCM-41-Cl with loading 56.5% linker.…”

Section: Methodsmentioning

confidence: 99%

A novel strategy for stabilization of sub-nanometric Pd colloids on kryptofix functionalized MCM-41: nanoengineered material for Stille coupling transformation

Alamgholiloo

Pesyan

Rostamnia

2021

Sci Rep

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The stabilization of sub-nanometric metal particles (< 1 nm) with suitable distribution remained challenging in the catalytic arena. Herein, an intelligent strategy was described to anchoring and stabilizing sub-nanometric Pd colloids with an average size of 0.88 nm onto Kryptofix 23 functionalized MCM-41. Then, the catalytic activity of Pd@Kryf/MCM-41 was developed in Stille coupling reaction with a turnover frequency (TOF) value of 247 h−1. The findings demonstrate that porous MCM-41 structure and high-affinity Kryptofix 23 ligand toward adsorption of Pd colloids has a vital role in stabilizing the sub-nanometric particles and subsequent catalytic activity. Overall, these results suggest that Pd@Kryf/MCM-41 is a greener, more suitable option for large-scale applications and provides new insights into the stabilization of sub-nanometric metal particles.

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“…Furthermore, the catalyst was able to be recycled for several consecutive runs (7)(8)(9)(10)(11)(12)(13)(14). Pzsyan et al [67] anchored the Cu-Koc acid complex (KA) on functionalized silica-MCM-41 by 3-chloropropyltrimethoxysilane (CPTMS) (MCM41-CPTMS-Kojic acid-Cu) (23) (Scheme 9). The copper(II) complex on Kojic acid-functionalized nano silica-MCM-41 (23) was investigated in the synthesis of 1,2,3-triazoles through the click reaction of 2-(azidomethyl)-5-benzyloxy-4-pyrone and azido Kojic acid with terminal alkynes in ethanol/water (1:1 v/v) and ethylene glycol (EG) as solvents at 100 • C within 5 to 30 min.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Copper-Based Solid Heterogeneous Catalysts for Azide–Alkyne Cycloaddition Reactions

Aflak

Ayouchia

Bahsis

et al. 2022

IJMS

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The copper(I)-catalyzed azide−alkyne cycloaddition (CuAAC) reaction is considered to be the most representative ligation process within the context of the “click chemistry” concept. This CuAAC reaction, which yields compounds containing a 1,2,3-triazole core, has become relevant in the construction of biologically complex systems, bioconjugation strategies, and supramolecular and material sciences. Although many CuAAC reactions are performed under homogenous conditions, heterogenous copper-based catalytic systems are gaining exponential interest, relying on the easy removal, recovery, and reusability of catalytically copper species. The present review covers the most recently developed copper-containing heterogenous solid catalytic systems that use solid inorganic/organic hybrid supports, and which have been used in promoting CuAAC reactions. Due to the demand for 1,2,3-triazoles as non-classical bioisosteres and as framework-based drugs, the CuAAC reaction promoted by solid heterogenous catalysts has greatly improved the recovery and removal of copper species, usually by simple filtration. In so doing, the solving of the toxicity issue regarding copper particles in compounds of biological interest has been achieved. This protocol is also expected to produce a practical chemical process for accessing such compounds on an industrial scale.

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Cu-Kojic Acid Complex Anchored to Functionalized Silica-MCM-41: A Promising Regioselective and Reusable Nanocatalyst for Click Reaction

Cited by 11 publications

References 49 publications

Zn Complex on Tryptophan-Functionalized MCM-41 as an Efficient and Promising Reusable Nanocatalyst in One-Pot Three-Component Synthesis of Amino Benzyl Quinolinols and Naphthols via a Betti Reaction

Zn Complex on Tryptophan-Functionalized MCM-41 as an Efficient and Promising Reusable Nanocatalyst in One-Pot Three-Component Synthesis of Amino Benzyl Quinolinols and Naphthols via a Betti Reaction

A novel strategy for stabilization of sub-nanometric Pd colloids on kryptofix functionalized MCM-41: nanoengineered material for Stille coupling transformation

Recent Advances in Copper-Based Solid Heterogeneous Catalysts for Azide–Alkyne Cycloaddition Reactions

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