A novel highly dispersive magnetic nanocatalyst in water : glucose as an efficient and green ligand for the immobilization of copper(<scp>ii</scp>) for the cycloaddition of alkynes to azides

Moghaddam, Firouz Matloubi; Saberi, Vahid; Kalhor, Sepideh; Ayati, Seyed Ebrahim

doi:10.1039/c6ra17137k

Cited by 15 publications

(7 citation statements)

References 38 publications

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“…In previous study, we tried to stabilize Cu 2+ onto the Fe 3 O 4 which was functionalized with glucose, in order to synthesize different derivatives of 1,2,3‐triazole via one‐pot three‐component reaction of alkynes, alkyl halides, and sodium azide. In this study, we made an effort to immobilize Pd 2+ onto the magnetic nanoparticles of Fe 3 O 4 –silica coated and usage of this nanocatalyst in the synthesis of benzoxazole derivatives with 2‐aminophenol and an aromatic aldehyde.…”

Section: Introductionmentioning

confidence: 99%

Palladium(II) Immobilized Onto the Glucose Functionalized Magnetic Nanoparticle as a New and Efficient Catalyst for the One‐pot Synthesis of Benzoxazoles

Moghaddam

Saberi

Kalhor

et al. 2018

Applied Organom Chemis

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Funding informationSharif University of Technology (SUT) Palladium(II) have been immobilized into the nano magnetic Fe 3 O 4 which was functionalized with glucose in order to achieve a one-pot synthesis of 2substituted benzoxazole derivatives with high yields in the diverse range of organic solvents. The nano catalyst is highly dispersive in polar solvents and can be easily recovered and reused for 6 runs without significant loss of its activity. Finally, the catalyst was fully characterized by FT-IR, TGA, CHN, SEM, EDX and atomic absorption spectroscopy.

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Section: Introductionmentioning

confidence: 99%

Palladium(II) Immobilized Onto the Glucose Functionalized Magnetic Nanoparticle as a New and Efficient Catalyst for the One‐pot Synthesis of Benzoxazoles

Moghaddam

Saberi

Kalhor

et al. 2018

Applied Organom Chemis

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“…The magnetic nanoparticle (Fe 3 O 4 ) was synthesized using the co-precipitation approach 101 , 102 . After synthesizing it, Fe 3 O 4 @SiO 2 (1 g) was dispersed in dry EtOH and NH 4 OH (2 mL) was added to the mixture.…”

Section: Methodsmentioning

confidence: 99%

Magnetic UiO-66 functionalized with 4,4′-diamino-2,2′-stilbenedisulfonic as a highly recoverable acid catalyst for the synthesis of 4H-chromenes in green solvent

Khodabakhshi

Baghersad

2022

Sci Rep

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According to 4H-chromenes importance, we synthesized a novel magnetic UiO-66 functionalized with 4,4′-diamino-2,2′-stilbenedisulfonic as an efficient and reusable solid acid catalyst for synthesizing 4H-chromene skeletons via a one-pot three components reaction in a green solvent. The structure of the synthesized catalyst was confirmed by various techniques including FT-IR, XRD, BET, TGA, TEM, EDX, and SEM, and also the product yields were obtained in 83–96% of yields for all the reactions and under mild conditions. The reported procedure presents an environmentally friendly approach for synthesizing a significant number of 4H-chromene derivatives. Correspondingly, MOF-based catalyst makes it easy to separate from reaction media and reuse in the next runs.

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“…In a related approach, many investigations explored the coating of nano-ferrites with a functionalized shell to reduce the aggregation of the nanoparticles in the solution and improve the catalyst's efficiency by increasing the number of functional groups on the surface. Among these, Moghaddam et al [132] reported the immobilization of glucose (GLU) onto MNPs of Fe 3 O 4 -silica to stabilize copper(II), and studied their catalytic activity under greener conditions for the one-pot [3+2] cycloaddition reaction of alkyl halides, sodium azide, and alkynes using water as solvent (Figure 11). The use of 5 mol% of (MNPs@GLU)Cl ( 33) catalyst produced excellent yields (76-99% in 1-8 h) in the synthesis of various 1,4-triazole derivatives at 50 • C, due to the high dispersity of the catalyst in water by creating hydrogen bonds with the glucose.…”

Section: Magnetic Solid-supported Catalysts For Cuaacmentioning

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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A novel highly dispersive magnetic nanocatalyst in water : glucose as an efficient and green ligand for the immobilization of copper(ii) for the cycloaddition of alkynes to azides

Abstract: A new heterogeneous and highly dispersive nanocatalyst in water was prepared by the immobilization of Cu2+ onto glucose on Fe3O4.

Cited by 15 publications

References 38 publications

Palladium(II) Immobilized Onto the Glucose Functionalized Magnetic Nanoparticle as a New and Efficient Catalyst for the One‐pot Synthesis of Benzoxazoles

Palladium(II) Immobilized Onto the Glucose Functionalized Magnetic Nanoparticle as a New and Efficient Catalyst for the One‐pot Synthesis of Benzoxazoles

Magnetic UiO-66 functionalized with 4,4′-diamino-2,2′-stilbenedisulfonic as a highly recoverable acid catalyst for the synthesis of 4H-chromenes in green solvent

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

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