Pd(II)-β-cyclodextrin complex: Synthesis, characterization and efficient nanocatalyst for the selective Suzuki-Miyaura coupling reaction in water

Kaboudin, Babak; Salemi, Hadi; Mostafalu, Ramin; Kazemi, Foad; Yokomatsu, Tsutomu

doi:10.1016/j.jorganchem.2016.06.007

Cited by 40 publications

(18 citation statements)

References 32 publications

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“…Considering the TEM images, in which the Pd nanoparticles are not detectable, it can be concluded that Pd nanoparticles can locate within the interlayer of sepiolite. Moreover, according to the literature, Pd can also be accommodated within the cavities of CDs . Hence, another possibility for accommodation of Pd nanoparticles is the cavities of CDs in CDNS.…”

Section: Resultsmentioning

confidence: 97%

Palladium nanoparticles immobilized on sepiolite–cyclodextrin nanosponge hybrid: Efficient heterogeneous catalyst for ligand‐ and copper‐free C─C coupling reactions

Sadjadi

Heravi

Raja

et al. 2018

Applied Organom Chemis

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A novel hybrid system composed of sepiolite clay and cyclodextrin nanosponge (CDNS) was prepared via reaction of Cl‐functionalized sepiolite with amine‐functionalized CDNS. CDNS–sepiolite was then applied for immobilization of Pd(0) nanoparticles. The resulting hybrid system, Pd@CDNS‐sepiolite, was characterized using various techniques and successfully used as an efficient and heterogeneous catalyst for ligand‐ and copper‐free Sonogashira and Heck coupling reactions under mild reaction conditions. Recycling experiments confirmed that Pd@CDNS‐sepiolite was recyclable and could be used for several consecutive reaction runs with slight Pd leaching and loss of catalytic activity.

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Section: Resultsmentioning

confidence: 97%

Palladium nanoparticles immobilized on sepiolite–cyclodextrin nanosponge hybrid: Efficient heterogeneous catalyst for ligand‐ and copper‐free C─C coupling reactions

Sadjadi

Heravi

Raja

et al. 2018

Applied Organom Chemis

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“…The coupling mechanism of Pd(+2/+4) was recognized by mercury drop test for this study. As a consequence of homogeneous nature of Pd (II), the catalyst efficiency fell down 26% after 4 runs . But, the present heterogeneous catalyst with coupling mechanism of Pd(0/+2) showed low loss in activity after six runs.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, magnetic nanoparticles are reported as an outstanding support for the heterogeneous catalysts . In addition to the inorganic supports for preparation of heterogeneous catalysts, some natural products such as cyclodextrins have been used as the stabilizer and dispersing reagents in compliance with green chemistry principles …”

Section: Introductionmentioning

confidence: 99%

The β‐cyclodextrin decorated with palladium nanoparticles without pretreatment: An efficient heterogeneous catalyst for biaryls synthesis

Feiz

Loni

Naderi

et al. 2018

Applied Organom Chemis

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Funding informationResearch Council of Shahid Beheshti University β-Cyclodextrin decorated with palladium nanoparticles (PdNPs@β-CD) without pretreatment led to a suitable catalyst for the biaryls synthesis in water. A simple and straightforward method was developed for the preparation of PdNPs@β-CD as a green catalyst. The prepared catalyst was characterized by Fourier-transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), X-ray diffraction (XRD), atomic absorption spectroscopy (AAS), transmission electron microscopy (TEM), and energy-dispersive X-ray spectroscopy (EDS) measurements. It was found that PdNPs@β-CD exhibits high performance in Ullmann, Suzuki and Hiyama coupling reactions.

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“…[27][28][29][30][31][32] Putta et al 33 reported the use of palladium nanoparticles (Pd NPs)-β-CD-graphene nanosheets (Pd@CD-GNS) as the catalyst for C-C coupling reactions and showed that this material exhibited excellent catalytic activity and dispersibility in water. Kaboudin et al 34 studied the preparation and catalytic activity of a novel Pd II -β-CD complex in Suzuki-Miyaura coupling reactions. In addition, Gruttadauria and co-workers 35 developed synthetic nanoparticle hybrids composed of poly(amidoamine) dendrimers and palladium (SWCNT-PAMAM 3.0-Pd) for the heterogeneous catalysis of Suzuki-Miyaura reactions.…”

Section: Introductionmentioning

confidence: 99%

Palladium Nanoparticles Supported on β-Cyclodextrin Functionalized Poly(amidoamine)s and Their Application in Suzuki-Miyaura Cross-Coupling Reactions

Zhang

Yao

Deng

2019

J. Braz. Chem. Soc.

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Herein, the synthesis, characterization and catalytic application of an organic-inorganic, palladium (Pd)-containing hybrid material, poly(amidoamine)-cyclodextrin (Pd@PAAs-CD), is reported as an efficient catalyst for Suzuki-Miyaura coupling reactions. The structure of Pd@PAAs-CD was confirmed by Fourier transform infrared spectroscopy (FTIR), transmission electron microscopy (TEM), scanning electron microscopy (SEM), inductively-coupled plasma atomic emission spectroscopy (ICP-AES), and 1 H nuclear magnetic resonance (NMR) spectroscopy. Furthermore, an efficient protocol has been developed using Pd@PAAs-CD as the catalyst in a Suzuki-Miyaura cross-coupling reaction in an aqueous medium in high yields. By using cyclodextrin (CD) as the mediator grafted onto PAAs, the Pd nanoparticles (NPs) were dispersed and enhanced the catalytic reaction by promoting host-guest interactions with the CD. In addition, the reusability of the Pd@PAAs-CD hybrid material is demonstrated for use in multiple sequential cross-coupling reactions. White solid; 1 H NMR (500 MHz, CDCl 3 ) d 6.78 (d, 1H, J 7.5 Hz, CH), 6.83 (t, 1H, J 7.9 Hz, CH), 7.13 (m, 2H, CH 2 ), 7.35 (m, 1H, CH), 7.45 (m, 4H, CH 2 ). Compound 3cWhite solid; 1 H NMR (500 MHz, CDCl 3 ) d 3.75 (s, 3H, OCH 3 ), 6.83 (m, 1H, CH), 7.15 (m, 2H, CH 2 ), 7.27 (m, 2H, CH 2 ), 7.38 (m, 2H, CH 2 ), 7.55 (m, 2H, CH 2 ); 13 C NMR

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Pd(II)-β-cyclodextrin complex: Synthesis, characterization and efficient nanocatalyst for the selective Suzuki-Miyaura coupling reaction in water

Cited by 40 publications

References 32 publications

Palladium nanoparticles immobilized on sepiolite–cyclodextrin nanosponge hybrid: Efficient heterogeneous catalyst for ligand‐ and copper‐free C─C coupling reactions

Palladium nanoparticles immobilized on sepiolite–cyclodextrin nanosponge hybrid: Efficient heterogeneous catalyst for ligand‐ and copper‐free C─C coupling reactions

The β‐cyclodextrin decorated with palladium nanoparticles without pretreatment: An efficient heterogeneous catalyst for biaryls synthesis

Palladium Nanoparticles Supported on β-Cyclodextrin Functionalized Poly(amidoamine)s and Their Application in Suzuki-Miyaura Cross-Coupling Reactions

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