A novel Fe<sub>3</sub>O<sub>4</sub>@TCH@Ni(II) nanoparticle: An efficient magnetically retrievable nanocatalyst for C–C and C–heteroatom bond formation reaction

Karkon, Elahe Gholamiyan; Mostafavi, Hossein

doi:10.1002/aoc.6824

Cited by 4 publications

(3 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Despite the considerable prospects of palladium catalysts in cross-coupling reactions, the high cost and possible toxicity of Pd have remained a scientific challenge, highlighting the need for developing and discovering alternative ways with an environmentally friendly and non-toxic catalytic system 12 – 14 . Numerous studies have reported the use of other transition metals, such as Ni 15 , 16 , Cu 17 , 18 , Fe 19 , 20 , and Co 21 , 22 for more appropriate, cost-effective, and safe approaches for cross-coupling reactions, over the past decade. Considerable attention has been given to copper catalysis, owing to its good functional group tolerance, the low cost of the catalysts, and low toxicity 23 , 24 .…”

Section: Introductionmentioning

confidence: 99%

Synergistic performance of a new bimetallic complex supported on magnetic nanoparticles for Sonogashira and C–N coupling reactions

Nasseri,

Kassaee

et al. 2023

Sci Rep

View full text Add to dashboard Cite

This paper describes the synthesis of a novel Cu–Ni bimetallic system comprising of magnetic nanoparticles, as the core, and 4-amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole (4-ABPT), as a conjugated bridge, between nickel and copper species. With low Cu and Ni loading (0.06 mol% Ni, 0.08 mol% Cu), the resulting Fe3O4@SiO2@4-ABPT/Cu–Ni showed to be a highly efficient catalyst for the Sonogashira and C–N cross-coupling reactions. The developed catalyst was well characterized by FT-IR, XRD, EDX-mapping, FE-SEM, TEM, ICP, VSM, TGA/DTG/DTA, LSV, and XPS techniques. Fe3O4@SiO2@4-ABPT/Cu–Ni nanocatalyst was compatible with a wide range of amines and aryl halides in the Sonogashira and C–N cross-coupling reactions and offered desired coupling products in high to excellent yields under palladium- and solvent-free conditions. Based on the XPS results, the 4-ABPT ligand can adjust electron transfer between Ni and Cu in Fe3O4@SiO2@4-ABPT/Cu–Ni, promoting the formation and stabilization of Cu+ and Ni3+ species. Electronic interactions and the synergistic effect between these metals increased the selectivity and activity of Fe3O4@SiO2@4-ABPT/Cu–Ni catalyst in the Sonogashira and C–N cross-coupling reactions compared with its monometallic counterparts. Additionally, the magnetic properties of Fe3O4@SiO2@4-ABPT/Cu–Ni facilitated its separation from the reaction mixture, promoting its reuse for several times with no significant loss in its catalytic activity or performance.

show abstract

Section: Introductionmentioning

confidence: 99%

Synergistic performance of a new bimetallic complex supported on magnetic nanoparticles for Sonogashira and C–N coupling reactions

Nasseri,

Kassaee

et al. 2023

Sci Rep

View full text Add to dashboard Cite

show abstract

“…[31][32][33][34][35] Also, according to the studies, magnetic nanocatalysts can be reused more than conventional catalysts. 36,37 Because of their high surface area, they generally exhibit higher catalytic activity than conventional heterogeneous acid catalysts. 38 In this research and following our continuing efforts on the synthesis of catalysts, 39 we would like to introduce the logical design, synthesis, and identification of the Fe 3 O 4 @CPTMS@Asp@Ni as an efficient heterogeneous catalyst and then was probed the performance of this novel nanocatalyst to promote the synthesis of acridine derivatives 4a-p by mixing aryl glyoxals 1a-h, cyclic 1,3-dione 2a,b and ammonium acetate (3) condensation under green condition (Figure 2).…”

Section: Introductionmentioning

confidence: 99%

Nickel‐asparagine complex fixed on a magnetic substrate as a precursor for preparing substituted acridines

Abbaszadehghan,

Poursattar Marjani,

Bibak

et al. 2023

Applied Organom Chemis

View full text Add to dashboard Cite

In this work, an efficient, novel, retrievable, and magnetic heterogeneous nanocatalyst, Fe3O4@CPTMS@Asp@Ni was successfully fabricated using Fe3O4 nanoparticles as the core that were coated with surfactant and 3‐chloropropyltrimethoxysilan and deposited asparagine and nickel metal that can be used in multicomponent reactions for the synthesis of acridines derivatives with high yield in short reaction times. The virtue of obtained nanocatalyst was identified using transmission electron microscopy, scanning electron microscopy, Fourier transform infrared spectroscopy, X‐ray diffraction analysis, energy dispersive X‐ray, Brunauer–Emmett–Teller, vibrating sample magnetometry, Raman, and thermogravimetric analysis. The X‐ray diffraction analysis studies demonstrate that the average crystallite sizes of the prepared nanocatalyst are estimated to be about 45.4 nm. Also, the vibrating sample magnetometry measurement shows saturation magnetization values (Ms) of 7 emu/g for Fe3O4@CPTMS@Asp@Ni nanocatalyst. Also, after the synthesis steps, the application of the prepared nanocatalyst in the preparation of acridine‐1,8(2H,5H)‐diones has been investigated. Then to evaluate and assess the efficiency of the nanocatalyst as mentioned above, and its effect on the synthesis of divergent acridines via a one‐pot, three‐component condensation reaction of cyclic 1,3‐dione, aryl glyoxal, with ammonium acetate in the water as green solvent was studied. Also, when investigating the reusability of this catalyst, it was observed that Fe3O4@CPTMS@Asp@Ni nanocatalyst could be reused at least five times without losing its efficiency. High efficiency, outstanding yields in quick intervals, easy separation using a magnetic field, and possessing reusability are significant benefits of the attained nanocatalyst.

show abstract

“…Therefore, developing and discovering alternative ways with a better environment-friendly and non-toxic catalytic system is necessary. Many studies have been reported about using other transition metals, such as Ni 13,14 , Cu 15,16 , Fe 17,18 , and Co 19,20 , over the past decade. They are reported as more appropriate, cost-effective, and safe approaches for cross-coupling reactions.…”

Section: Introductionmentioning

confidence: 99%

Conjugated Cu-Ni bimetallic complex supported on Fe 3 O 4 @SiO 2 : An efficient nanocatalyst with synergistic performance for the solvent-free Sonogashira, and C-N cross-couplings

Nasseri

Kassaee

et al. 2023

Preprint

View full text Add to dashboard Cite

Synthesis of a novel Cu-Ni bimetallic system comprising magnetic nanoparticles as the core and 4-amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole (4-ABPT) as a conjugated bridge between nickel and copper species is described. With low Cu and Ni loading (0.06 mol% Ni, 0.08 mol% Cu), the resulting Fe3O4@SiO2@4-ABPT/Cu-Ni is discovered to be a highly efficient catalyst for the Sonogashira and C-N cross-coupling reactions. It is well characterized by FT-IR, XRD, EDX, FE-SEM, TEM, ICP, VSM, TGA/DTG/DTA, and XPS techniques. Fe3O4@SiO2@4-ABPT/Cu-Ni as a nanocatalyst in the Sonogashira and C-N cross-coupling reactions is compatible with a wide range of amines and aryl halides and gives desired coupling products in high to excellent yields under palladium- and solvent-free conditions. The XPS results show that the 4-ABPT as a ligand can adjust electron transfer between Ni and Cu in Fe3O4@SiO2@4-ABPT/Cu-Ni, which promotes the formation and stabilization of Cu+ and Ni3+ species. Electronic interactions and the synergistic effect between these metals increase the selectivity and activity of Fe3O4@SiO2@4-ABPT/Cu-Ni as a catalyst in the Sonogashira and C-N cross-coupling reactions in comparison with its monometallic counterparts. Additionally, the magnetic properties of the Fe3O4@SiO2@4-ABPT/Cu-Ni make it easy to separate from the reaction mixture, and it can be reused several times without a significant loss in its catalytic activity or performance.

show abstract

A novel Fe₃O₄@TCH@Ni(II) nanoparticle: An efficient magnetically retrievable nanocatalyst for C–C and C–heteroatom bond formation reaction

Cited by 4 publications

References 49 publications

Synergistic performance of a new bimetallic complex supported on magnetic nanoparticles for Sonogashira and C–N coupling reactions

Synergistic performance of a new bimetallic complex supported on magnetic nanoparticles for Sonogashira and C–N coupling reactions

Nickel‐asparagine complex fixed on a magnetic substrate as a precursor for preparing substituted acridines

Conjugated Cu-Ni bimetallic complex supported on Fe 3 O 4 @SiO 2 : An efficient nanocatalyst with synergistic performance for the solvent-free Sonogashira, and C-N cross-couplings

Contact Info

Product

Resources

About

A novel Fe3O4@TCH@Ni(II) nanoparticle: An efficient magnetically retrievable nanocatalyst for C–C and C–heteroatom bond formation reaction

Cited by 4 publications

References 49 publications

Synergistic performance of a new bimetallic complex supported on magnetic nanoparticles for Sonogashira and C–N coupling reactions

Synergistic performance of a new bimetallic complex supported on magnetic nanoparticles for Sonogashira and C–N coupling reactions

Nickel‐asparagine complex fixed on a magnetic substrate as a precursor for preparing substituted acridines

Conjugated Cu-Ni bimetallic complex supported on Fe 3 O 4 @SiO 2 : An efficient nanocatalyst with synergistic performance for the solvent-free Sonogashira, and C-N cross-couplings

Contact Info

Product

Resources

About

A novel Fe₃O₄@TCH@Ni(II) nanoparticle: An efficient magnetically retrievable nanocatalyst for C–C and C–heteroatom bond formation reaction