Novel Magnetically-Recyclable, Nitrogen-Doped Fe3O4@Pd NPs for Suzuki–Miyaura Coupling and Their Application in the Synthesis of Crizotinib

Abstract

Novel magnetically recyclable Fe3O4@Pd nanoparticles (NPs) were favorably synthesized by fixing palladium on the surface of nitrogen-doped magnetic nanocomposites. These catalysts were fully characterized by Fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), transmission electron microscopy (TEM), thermogravimetric analysis (TG), and X-ray photoelectron spectroscopy (XPS). The prepared catalyst exhibited good catalytic activity for Suzuki–Miyaura coupling reactions of aryl or heteroaryl halides (I, Br, Cl) with arylboronic acids. These as-prepared catalysts could be readily isolated from the reaction liquid by an external magnet and reused at least ten times with excellent yields achieved. In addition, using this protocol, the marketed drug crizotinib (anti-tumor) could be easily synthesized.

Microwave-Assisted Regioselective Suzuki Coupling of 2,4-Dichloropyrimidines with Aryl and Heteroaryl Boronic Acids

“…Solid-supported catalysts represent an attractive approach in the field of green organic chemistry, since they can often be recycled without loss of activity, in addition to the products and solution waste remaining free from metal contamination [35]. Despite several successful applications in Suzuki-Miyaura coupling [36][37][38], no product was formed when palladium on multiwall carbon nanotubes was used as a catalyst. Additionally, the screening was performed on a set of classic and solid-supported catalysts Pd(OAc) 2 with PPh 3 and Pd(OAc) 2 with PPh 3 on DVB, respectively, with the latter exhibiting inferior catalytic ability and yield in our model reaction.…”

Recent Progress of Metal Nanoparticle Catalysts for C–C Bond Forming Reactions

“…To improve the catalytic activity, nitrogen-doped materials are used as a support [123,124]. According to this idea, Shen and Qiao et al synthesized novel magnetically Fe 3 O 4 @Pd NPs by fixing Pd on the surface of nitrogen-doped magnetic nanocomposites (Scheme 8) [125]. Hajipour et al synthesized magnetically separable nano-nickel catalysts, which catalyzed efficiently for fluoride-free Hiyama coupling reaction, through a "click" reaction of azidefunctionalized magnetic nanoparticles with 2-ethynylpyridine followed by immobilization of nickel nanoparticles [126].…”

Ruthenium Supported on Ionically Cross-linked Chitosan-Carrageenan Hybrid MnFe2O4 Catalysts for 4-Nitrophenol Reduction

“…The development of magnetic-supported catalyst that works on a wide range of application such as C-C coupling reaction, waste water treatment, and heavy metal removal has been extensively studied [20][21][22]. The magnetic-supported catalysts have a magnetic nature that allows for simple separation and recovery from the reaction medium by an external magnetic field [23].…”