Immobilizing palladium on melamine‐functionalized magnetic nanoparticles: An efficient and reusable phosphine‐free catalyst for Mizoroki–Heck reaction

• Published in: Applied organometallic chemistry Vol. 35; no. 5
• Main Authors: Aryanasab, Fezzeh, Shabanian, Meisam, Laoutid, Fouad, Vahabi, Henri
• Format: Journal Article
• Language: English
• Published: HOBOKEN Wiley 01.05.2021; Wiley Subscription Services, Inc
• Subjects: Alkenes; Atomic absorption analysis; Atomic beam spectroscopy; Bromides; Catalysts; Catalytic activity; Chemical synthesis; Chemistry; Chemistry, Applied; Chemistry, Inorganic & Nuclear; Cross coupling; CC coupling reactions; Fourier transforms; Functional groups; Halides; Heterogeneity; heterogeneous catalyst; Infrared analysis; Infrared spectroscopy; Iron oxides; magnetic nanoparticles; Magnetometers; Melamine; Nanoparticles; Palladium; Phosphines; Photoelectrons; Physical Sciences; Science & Technology; Spectrum analysis; supported palladium catalyst; Thermogravimetric analysis; X ray photoelectron spectroscopy; heterogeneous catalyst; supported palladium catalyst; C coupling reactions; magnetic nanoparticles; C&#63743
• ISSN: 0268-2605; 1099-0739
• DOI: 10.1002/aoc.6198

A highly efficient and stable heterogeneous catalyst was successfully prepared by anchoring palladium(0) onto melamine‐functionalized Fe3O4 magnetic nanoparticles (MNPs‐Mel‐Pd). With the aid of amine functional groups, melamine was covalently bonded on epoxy functionalized magnetic nanoparticles and then Pd(0) was immobilized on this support with high dispersion. The prepared nanocatalyst exhibits excellent catalytic activity for CC cross coupling (Mizoroki–Heck) of various aryl halides (iodide, bromides, and chrlorides) with olefins under mild reaction condition in relatively short reaction times. The synthesized nanocatalyst was characterized using Fourier transform infrared (FT‐IR) spectroscopy, X‐ray diffraction (XRD), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), vibrating sample magnetometer (VSM), and X‐ray photoelectron spectroscopy (XPS) techniques. The loading level of Pd in MNPs‐Mel‐Pd catalyst was measured to be 1.26 × 10−3 mol g−1 by atomic absorption spectroscopy (AAS). In addition, the catalyst can be easily separated and recovered from the reaction mixture by using an external magnet. The heterogeneity of the catalyst was confirmed by the hot filtration test, which was reused for at least six times under the optimized conditions without any significant loss of its activity. A new phosphine‐free, heterogeneous magnetic nanoparticle‐supported Pd catalyst (MNPs‐Mel‐Pd) was synthesized, and its activity in Mizoroki–Heck CC coupling reaction is reported.