Nickel–palladium bimetallic nanoparticles supported on multi-walled carbon nanotubes; versatile catalyst for Sonogashira cross-coupling reactions

Wilson, Katherine A.; Picinich, Lacey A.; Siamaki, Ali R.

doi:10.1039/d3ra00027c

Cited by 3 publications

(4 citation statements)

References 81 publications

(94 reference statements)

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“…Copper is crucial for cross-coupling reactions, but it suffers from several drawbacks like low activity and a propensity for oxidative homo-coupling reactions 21 , 26 . The drawbacks can be optimized by the introduction of a second metal into a Cu monometallic sample as a Cu–M bimetallic catalytic system.…”

Section: Introductionmentioning

confidence: 99%

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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

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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.

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Section: Introductionmentioning

confidence: 99%

“…Ni has a high bonding affinity with sufficient flexibility to generate multiple oxidation states 30 , 31 . Furthermore, metal-catalyzed cross-coupling processes show that nickel is as reactive as palladium 26 .…”

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

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“…Copper is crucial for cross-coupling reactions, but it also has drawbacks like low activity and a propensity for oxidative homo-coupling reactions 19,23 . The mentioned problems can be optimized by introducing a second metal into a Cu monometallic sample as a Cu-M bimetallic catalytic system.…”

Section: Introductionmentioning

confidence: 99%

“…The metal has a high bonding affinity and is flexible enough to generate multiple oxidation states 27,28 . Furthermore, metal-catalyzed cross-coupling processes show that nickel is as reactive as palladium 23 . Over the past twenty years, several attempts have been made to extend heterogenous Cu-Ni bimetallic catalysts for improved 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

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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.

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Cellulose/silica supported Schiff base Pd(II) catalyst for copper-free Sonogashira cross-coupling

Pharande,

Mhaldar,

Patil

et al. 2023

Res Chem Intermed

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Nickel–palladium bimetallic nanoparticles supported on multi-walled carbon nanotubes; versatile catalyst for Sonogashira cross-coupling reactions

Abstract: Nickel–palladium bimetallic nanoparticles supported on multi-walled carbon nanotubes (Ni–Pd/MWCNTs) were successfully employed in Sonogashira cross-coupling reactions with functionalized aryl halides and terminal alkynes.

Cited by 3 publications

References 81 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

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

Cellulose/silica supported Schiff base Pd(II) catalyst for copper-free Sonogashira cross-coupling

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