Copper(II) chelate-bonded magnetite nanoparticles: A new magnetically retrievable catalyst for the synthesis of propargylamines

Abstract

In this study, we document the use of a reusable magnetic nanoparticle (MNP)-supported copper catalyst for the efficient synthesis of propargylamines via the A 3 coupling of benzaldehydes, phenylacetylene, and piperidine or morpholine. The new MNPs were characterized by scanning electron microscopy, energy dispersive X-ray analysis, Fourier transform infrared spectroscopy, thermogravimetric analysis, and vibrating sample magnetometry. Notably, the activity and leaching test of the catalyst indicated that the MNPs could be reused without loss to its catalytic activity or leaching of its copper ligands.

A Review on Recent Advances in the Application of Nanocatalysts in A3 Coupling Reactions

“…In 2017, Sayyahi et al. successfully synthesized a copper(II) chelate‐bonded magnetite NPs through immobilization of copper(II)‐imine complex on to the surface of silica‐coated magnetite (Cu‐imine ligand@SiO 2 @Fe 3 O 4 MNPs) (Scheme ) . The as‐prepared complex shows a long‐term catalytic stability and high catalytic activity in A 3 coupling of benzaldehydes, piperidine or morpholine and phenylacetylene in the absence of solvent at 80 °C (Scheme ).…”

“…It is important to stress that despite huge advancements of the reported works in the literature, another important challenges in the A 3 coupling reactions is nature of solvent and kind of the catalyst. A number of nanocatalysts, including copper, silver, gold, nickel, magnetic nanocatalysts and Co 3 O 4 , ZnS and nanopowder zinc titanate were successfully applied for A 3 coupling reactions with yields ranging from good to excellent in appropriate times in organic solvents or aqueous medium . The authors ascribed high catalytic activity of nanocatalysts to the particles size.…”

Cobalt‐Catalyzed Three‐Component Synthesis of Propargylamine Derivatives and Sonogashira Reaction: A Comparative Study between Co‐NPs and Co‐NHC@MWCNTs

“…In general, several reports about propargylamine derivatives synthesis are available which in almost of them common secondary amines such as piperidine, pyrrolidine and morpholine and special conditions (high reaction temperature or long reaction time) was applied. [16][17][18][19][20][21] Imidazole have resonance electrons and it categorized as unreactive amine, therefore a few studies on the application of this substrate in this coupling reaction have been reported. We explored the generality of Co-NHC@MWCNTs and Co-NPs catalysts application with different substrate to prepare a series of propargylamine derivatives ( Table 2).…”

“…The results was given is Table 4. As can be [17] in water at 60°C 2 / 80 5 Cu 2 O-NPs [19] Cu (3 mol %), CH 2 Cl 2 , 60°C 5 / 92 6 Cu-NPs [18] Cu(5 mol %),solvent-free, 80°C…”

[Fe3O4@SiO2@(C3H6)2-(Imidazolium)2-Butyl][MnCl42-] as a novel nanomagnetic catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives

“…In view of the advantages of magnetic nanoparticles and ILs, some magnetic ILs composites have been developed [26,27]. Following our ongoing efforts for the development of more benign and efficient nanocatalysts [28][29][30][31], herein, we present the design and preparation and use of [Fe 3 O 4 @SiO 2 @(C 3 H 6 ) 2 -(Imidazolium) 2…”