Efficient Sonogashira and A³ coupling reactions catalyzed by biosynthesized magnetic Fe₃O₄@Ni nanoparticles from Euphorbia maculata extract

Abstract

In this work, biosynthesized Fe3O4@Ni nanoparticles using Euphorbia maculata aqueous have been used as effective catalysts in the synthesis of 2,3‐disubstituted benzo[b]furan derivatives using three component coupling of aldehydes, secondary amines and alkynes (A3 coupling reaction). Using novel nanoscale materials, the current green, practical and economical method leads to short reaction times and high yields. The biosynthesized catalyst was also successfully employed in the Sonogashira cross‐coupling reactions of various aryl halides with phenylacetylene. The best performance was observed using just 20 mg of the catalyst and ethanol as a green solvent. The developed protocol provides easy workup, short reaction times and good to excellent product yields. Furthermore, since the composite is highly stable, an external permanent magnet can be easily used for separating the catalyst. Thus, the catalyst can be recycled several times without considerable loss of catalytic activity.

Reduced zwitterionic graphene oxide sheets decorated with nickel nanoparticles as magnetically and efficient catalyst for A3‐coupling reactions under optimized green experimental conditions

“…In the last 10 years, green chemistry is one of the most important societal challenges. [ 60–62 ] In this framework, it is important to measure the green performances for the A 3 ‐coupling reaction so that we have evaluated some green metrics such as: the environmental factor ( E ‐factor), which provides information about the wastes generated in the process (Equation ) [ 59 ] : …”

“…In the initial step, the rGO‐BPED‐PS@NiNPs catalyst activates the CH bond of the terminal alkyne generating a NiNPs‐acetylide complex on the surface of the GO‐BPED‐PS, as discussed in the literature. [ 62 ] The second step includes the coupling reaction between the NiNPs‐acetylide complex and the iminium ion, which is produced by the condensation reaction between the secondary amine group and the aldehyde group yielding the expected propargylamine. However, the mechanism is not really elucidated because it was reported in the literature that metal nanoparticles act as a redox catalyst via a free radical mechanism.…”

Recent advances in non-noble metal-based oxide materials as heterogeneous catalysts for C–H activation

“…, Fe 3 O 4 @Ni nanoparticles, was biosynthesized by Alinezhad et al for the Sonogashira reaction under mild conditions with a very high yield of coupled product (Table 2, entry 3). 51 The catalyst was believed to activate the terminal C–H bond of phenylacetylene to proceed with the reaction. The detailed mechanism for the Fe 3 O 4 @Ni-catalyzed Sonogashira reaction is depicted in Fig.…”

Efficient One-Pot Synthesis of 1,4-Dihydropyridines Catalyzed by Magnetic MnFe2O4 Nanoparticles

“…40 Because of the advantages of magnetic nanoparticles, such as low-cost large-scale synthesis, easy separation and reuse using an external magnet, and applicability in industrial processes, their use as catalysts in various organic reactions has been developed. [41][42][43][44][45][46][47] In this research, we describe a useful and simple method for the preparation of 1,4-dihydropyridines from the condensation of ethyl acetoacetate, various aldehydes, and ammonium acetate as a source of ammonia using magnetic MnFe 2 O 4 nanoparticles as a catalyst and ethanol as a solvent.…”