Copper‐Functionalized Silica‐Coated Magnetic Nanoparticles for an Efficient Suzuki Cross‐Coupling Reaction

Abstract

In this study, a new, efficient and inexpensive strategy has been developed based on the heterogeneous copper catalyst for the synthesis of different biaryl compounds via the Suzuki–Miyaura cross‐coupling reaction. In this respect, the core@shell modified Fe3O4@SiO2 magnetic nanoparticles (MNPs) has been prepared by immobilization of aminoguanidine and then the copper (II) ion into the surface of magnetic nanoparticles. After full characterization of the prepared catalyst by various technique such as TEM, SEM, EDX, TGA, XRD, VSM, ICP and FT‐IR, its catalytic activity has been investigated in the synthesis of different biarly compounds through the Suzuki‐Miyaura cross‐coupling reaction. Interestingly, similar to Pd‐based catalysts, this new heterogeneous Cu‐based catalyst can catalyze the Suzuki–Miyaura reaction in solvent free condition with good to excellent yields. Besides, this heterogeneous nano copper catalyst was able to separate from the reaction mixture by easy separation procedures and can reuse more than six runs.

Silica-coated magnetic nanoparticles functionalized cobalt complex: a recyclable and efficient catalyst for the C−C bond formation

“…It is worth noting that in the XRD pattern of Fe 3 O 4 @ SiO 2 -CT-Co, the diffraction peaks corresponding to cobalt ions have not been observed in the final catalyst, in agreement with the high cobalt dispersion [61]. The absence of Co diffraction peaks indicates the formation of finely dispersed cobalt species after immobilization on the surface of modified SiO 2 that are not detectable by this technique (as cobalt loading is lower than 5 wt% according to ICP results) [19,62,63].…”

“…During the last decades, miscellaneous transition metal catalysts especially palladium-based catalysts have been used to construct various organic and bioorganic molecules via Suzuki-Miyaura cross-coupling reaction. Since palladium catalysts have some drawbacks like air sensitivity, high cost, and toxicity, efforts have been highly focused on designing effective transition metal catalysts including cobalt [14][15][16][17], copper [18][19][20], nickel [21][22][23], and zinc [24,25] instead of using catalysts based on expensive metals like palladium [26][27][28]. Among all of the transition metal catalysts used in carbon-carbon coupling reactions, cobalt has gained great attention due to its precious properties such as eco-friendly, low cost, nontoxicity, and good availability; therefore, many studies have shown the implementation of catalytic systems based on cobalt with the usage of various linkers in carbon-carbon coupling reactions [16,29,30].…”

“…As a part of our ongoing work to design the efficient heterogeneous catalyst with eco-friendly methods [55], we prepared the silica-coated magnetic Fe 3 O 4 NPs (Fe 3 O 4 @SiO 2 ) with excellent magnetic features and inexpensive procedures according to the reported literature [19]. In the following step, the creatine amino acid as an organic ligand was added to the ethanoic mixture of Fe 3 O 4 @SiO 2 to afford Fe 3 O 4 @ SiO 2 -CT.…”

Green Synthesis of Cu Nanoparticles in Modulating the Reactivity of Amine-Functionalized Composite Materials towards Cross-Coupling Reactions

“…Pary et al described Cu 2 O nanoparticle-mediated oxidative C–C coupling reactions [ 25 ]. Sonei et al reported that Copper-functionalized silica-coated magnetic nanoparticles catalyst gives good to excellent yields at 80 °C in Suzuki-Miyuara cross-coupling reaction under solvent-free conditions [ 26 ].…”

“…In organic synthesis, the Ullmann C-C homocoupling, C-N, and C-O hetero coupling reactions are essential tools to prepare the bi-aryl, di-aryl amine and di-aryl ether structures. These are analogues to many natural products and precursors in synthesizing many biologically active complexes [ 23 , 24 , 25 , 26 , 27 , 28 ].…”