What is a cross-coupling? An argument for a universal definition

Reimann, Christopher E.; Kim, Kelly E.; Rand, Alexander W.; Moghadam, Farbod A.; Stoltz, Brian M.

doi:10.1016/j.tet.2022.133176

Cited by 2 publications

(1 citation statement)

References 76 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Carbon-carbon and carbon-heteroatom cross-coupling reactions, which traditionally apply palladium catalysts, are among the most significant chemical processes in organic synthesis [1][2][3][4] . A look at the development of these reactions indicates their applications in materials science, agrochemical compounds, electronic materials, and polymers area [5][6][7] .…”

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

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

show abstract

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

What is a cross-coupling? An argument for a universal definition

Cited by 2 publications

References 76 publications

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

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

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

Contact Info

Product

Resources

About