Suzuki, Stille and Heck cross-coupling reactions catalyzed by Fe<sub>3</sub>O<sub>4</sub>@PTA–Pd as a recyclable and efficient nanocatalyst in green solvents

Ghorbani‐Choghamarani, Arash; Norouzi, Masoomeh

doi:10.1039/c6nj00088f

Cited by 35 publications

(14 citation statements)

References 29 publications

(29 reference statements)

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“…Polyethylene glycol (PEG) is an alternative cross-coupling medium, as demonstrated for Stille, Suzuki, and Heck reactions, 302 and Sonogashira reactions. 303 A variety of relatively low molecular weight PEG oligomers are applicable as a solvent for cross-coupling reactions, and the higher molecular weight polymers can be used as additives and catalyst supports.…”

Section: Polyethylene Glycolmentioning

confidence: 99%

Solvent effects in palladium catalysed cross-coupling reactions

et al. 2019

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Section: Polyethylene Glycolmentioning

confidence: 99%

Solvent effects in palladium catalysed cross-coupling reactions

et al. 2019

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“…The bands for Fe‐O stretching for Fe 3 O 4 ‐Lignin and Fe 3 O 4 ‐Lignin@Pd‐NPs were observed at ῡ, 574 and 572 cm −1 respectively. [ 19e,25 ] The stretching vibrational band for O‐H group was observed at around ῡ, 3,440 cm −1 which showed blue shift of ῡ, 51 cm −1 when compared to this band in the IR spectrum of Lignin. [ 14,24 ] FT‐IR spectroscopy was used as one of the technique for the determination of nature of binding in the catalyst Fe 3 O 4 ‐Lignin@Pd‐NPs .…”

Section: Resultsmentioning

confidence: 99%

Fe₃O₄‐Lignin@Pd‐NPs: A highly efficient, magnetically recoverable and recyclable catalyst for Mizoroki‐Heck reaction under solvent‐free conditions

Bharamanagowda

Kumar

2020

Applied Organom Chemis

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Palladium nanoparticles (Pd‐NPs) were synthesized under green conditions in water by chemical reduction of PdCl2 with NaOH and supported by Fe3O4‐Lignin. Fe3O4‐Lignin is an organic–inorganic hybrid core‐shell was synthesized by sonication of a mixture of Fe3O4‐NPs (20 nm) and alkali lignin. The new materials Fe3O4‐Lignin and Fe3O4‐Lignin@Pd‐NPs were characterized by PXRD, SEM and FT‐IR spectroscopy. The Fe3O4‐Lignin@Pd‐NPs was further confirmed by UV–Visible spectroscopy, TEM, EDX, HRICP‐AES and TGA/DTA. The average size of Pd‐NPs determined from PXRD was 5–10 nm. The amount of palladium loaded on Fe3O4‐Lignin obtained from EDX analysis was 26.63% by mass. The amount of Fe and Pd present in the catalyst obtained from HRICP‐AES was 11.88 (wt. %) and 10.90 (wt. %) respectively per gram of lignin. The catalytic potential of Fe3O4‐Lignin@Pd‐NPs was evaluated in Mizoroki‐Heck C‐C coupling reaction. During the optimization studies of reaction between iodobenzene and n‐butyl acrylate in various solvents and under solvent‐free but aerobic conditions using various inorganic and organic bases, the product n‐butyl 3‐phenylprop‐2‐enoate (1a) obtained was as high as 95% in highly polar solvents as short as in 10 min and 99% under solvent‐free conditions in 3 min at 140 °C using n‐Pr3N as base. The scope of the above catalyst was investigated in the Mizoroki‐Heck reaction of various aryl/heterocyclic halides and n‐butyl acrylate/styrene under optimized solvent‐less conditions. The corresponding products were obtained in high yields (73–99%). The catalyst recovered by magnetic decantation was reused for five times in the C‐C coupling reaction between iodobenzene and n‐butyl acrylate which yielded 90–95% of the desired product, 1a.

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“…Ghorbani-Choghamarani and co-workers modified the surface of silica-coated Fe 3 O 4 NPs with a tridentate‒Pd complex. Magnetic NPs were prepared through the coprecipitation method; coating these nanoparticles with tridentate ligand gave functionalized magnetic NPs whose subsequent reaction of Pd(OAc) 2 with these immobilized ligands resulted in Fe 3 O 4 @PTA-Pd as a recyclable and efficient nanocatalyst ( Scheme 43 ) [ 43 ]. The focus of the present research was on the investigation of the recycling, reusability, and stability of the catalyst.…”

Section: Novel Types Of Magnetic Nanoparticles-supported Palladiummentioning

confidence: 99%

“… Suzuki‒Miyaura, Stille, and Heck cross-coupling reactions catalyzed by Fe 3 O 4 @PTA-Pd nanocatalyst [ 43 ]. …”

Section: Figures and Schemesmentioning

confidence: 99%

Advances in Magnetic Nanoparticles-Supported Palladium Complexes for Coupling Reactions

Nasrollahzadeh

2018

Molecules

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Carbon‒carbon (C‒C) and carbon‒heteroatom (C‒X) bonds that form via transition-metal-catalyzed processes have been extensively used in the organic synthesis and preparation of natural products and important compounds such as heterocycles, biologically active molecules, and dendrimers. Among the most significant catalysts, magnetic nanoparticles-supported palladium complexes are very effective, versatile, and heterogeneous catalysts for a wide range of C‒C and C‒X coupling reactions due to their reusability, thermal stability, and excellent catalytic performance. In this review, recent advances to develop magnetic nanoparticles supported palladium complexes, including their preparation, characterization, catalytic application, and reusability in the formation of both C‒C and C‒X bonds, by authors such as Sonogashira, Heck, Suzuki‒Miyaura, and Stille, and a few examples concerning N-arylation, S-arylation, and Csp2-P coupling reactions are discussed.

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Suzuki, Stille and Heck cross-coupling reactions catalyzed by Fe₃O₄@PTA–Pd as a recyclable and efficient nanocatalyst in green solvents

Abstract: A novel heterogeneous Pd-catalyst was designed and successfully employed in C–C coupling reactions under green conditions.

Cited by 35 publications

References 29 publications

Solvent effects in palladium catalysed cross-coupling reactions

Solvent effects in palladium catalysed cross-coupling reactions

Fe₃O₄‐Lignin@Pd‐NPs: A highly efficient, magnetically recoverable and recyclable catalyst for Mizoroki‐Heck reaction under solvent‐free conditions

Advances in Magnetic Nanoparticles-Supported Palladium Complexes for Coupling Reactions

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Suzuki, Stille and Heck cross-coupling reactions catalyzed by Fe3O4@PTA–Pd as a recyclable and efficient nanocatalyst in green solvents

Abstract: A novel heterogeneous Pd-catalyst was designed and successfully employed in C–C coupling reactions under green conditions.

Cited by 35 publications

References 29 publications

Solvent effects in palladium catalysed cross-coupling reactions

Solvent effects in palladium catalysed cross-coupling reactions

Fe3O4‐Lignin@Pd‐NPs: A highly efficient, magnetically recoverable and recyclable catalyst for Mizoroki‐Heck reaction under solvent‐free conditions

Advances in Magnetic Nanoparticles-Supported Palladium Complexes for Coupling Reactions

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Suzuki, Stille and Heck cross-coupling reactions catalyzed by Fe₃O₄@PTA–Pd as a recyclable and efficient nanocatalyst in green solvents

Fe₃O₄‐Lignin@Pd‐NPs: A highly efficient, magnetically recoverable and recyclable catalyst for Mizoroki‐Heck reaction under solvent‐free conditions