Synthesis and applications of polymeric N-heterocyclic carbene palladium complex-grafted silica as a novel recyclable nano-catalyst for Heck and Sonogashira coupling reactions

Tamami, Bahman; Farjadian, Fatemeh; Ghasemi, Soheila; Allahyari, Hamed

doi:10.1039/c3nj41137k

Cited by 65 publications

(46 citation statements)

References 63 publications

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“…After the reaction, the supported catalyst was recovered by filtration and reused up to six times without changes in the obtained results. Moreover, PdNPs immobilized in polymeric N-heterocyclic carbene grafted-silica 40 exhibited an excellent activity in Sonogashira coupling processes [79]. Aryl iodides, bromides and chlorides, as well as heterocyclic halides coupled with phenylacetylene afforded the corresponding products, the presence of TBAB (0.01 mol%) being required when using aromatic chlorides.…”

Section: Functionalized Silica-supported Palladium Catalystsmentioning

confidence: 99%

Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

et al. 2018

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Abstract:The Sonogashira cross-coupling reaction is the most frequently employed synthetic procedure for the preparation of arylated alkynes, which are important conjugated compounds with multiple applications. Despite of their rather high price, this reaction is usually catalyzed by palladium species, making the recovery and reuse of the catalyst an interesting topic, mainly for industrial purposes. Easy recycle can be achieved anchoring the palladium catalyst to a separable support. This review shows recent developments in the use of palladium species anchored to different solid supports as recoverable catalysts for Sonogashira cross-coupling reactions.

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Section: Functionalized Silica-supported Palladium Catalystsmentioning

confidence: 99%

Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

et al. 2018

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“…[49] And in 2009, Han et al used a poly(vinylpyrrolidone)-Ru-complex-grafted silica as a catalyst for the hydrogenation of aromatics. [50] In continuation of our previous projects on heterogeneous Pd catalysts based on polymeric supports, [51][52][53][54] polymer-grafted silica, [55][56][57] and our related publication on the synthesis and application of poly(4-vinylpyridine)ÀPd-grafted silica (Si-P4VPy-Pd) as a new heterogeneous catalyst in Heck and Suzuki crosscoupling reactions, [58] herein we report a Sonogashira crosscoupling reaction that uses Si-P4VPy-Pd as well as our newly synthesized and very promising comparatively cheap Si-P4VPy-Ni catalyst.…”

Section: Introductionmentioning

confidence: 98%

Poly(vinylpyridine)‐Grafted Silica Containing Palladium or Nickel Nanoparticles as Heterogeneous Catalysts for the Sonogashira Coupling Reaction

Farjadian¹,

Tamami²

2014

ChemPlusChem

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Efficient catalytic systems based on palladium and nickel nanoparticles supported on poly(4‐vinylpyridine) (P4VPy)‐grafted silica were prepared. After preparation of P4VPy‐grafted silica, complexation with PdCl2 and NiCl2 was carried out to obtain the heterogeneous catalytic systems. Scanning and transmission electron microscopy (SEM and TEM) showed that palladium and nickel particles on the nanoscale were dispersed throughout the surface. Under copper‐, amine‐, and phosphine‐free conditions, the palladium catalyst exhibited excellent activity in the Sonogashira cross‐coupling reaction. An amine‐ and phosphine‐free nickel‐catalyzed Sonogashira reaction in the presence of CuI as a cocatalyst was also performed successfully. In both systems phenylacetylene reacted with aryl iodides, bromides, and chlorides in high yield and over short reaction times.

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“…To our knowledge, noble metal palladium is a favourable catalyst for catalyzing a series of coupling reactions to form C-C bond and C-N bond [8][9][10][11][12]. In particular, homogeneous palladium catalyst has shown superior catalytic activity for catalyzing Sonogashira cross-coupling reaction.…”

Section: Introductionmentioning

confidence: 99%

Fabrication of PEI grafted Fe₃O₄/SiO₂/P(GMA-co-EGDMA) nanoparticle anchored palladium nanocatalyst and its application in Sonogashira cross-coupling reactions

Zhang

Tian

et al. 2015

New J. Chem.

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A novel magnetic Fe 3 O 4 /SiO 2 /P(GMA-co-EGDMA) composite nanoparticles grafted with hyperbranched/linear polyethylenimine ligand was fabricated. Subsequently, Nano palladium was effectively anchored on this carrier through the complexation between Pd 2+ ions and multifunctional organic ligands, then a novel supported Pd nanoparticles catalyst with good dispersion and high loading of Pd nanoparticles was successfully prepared after the follow reduction process. Afterwards, the as-prepared supported Pd nanoparticles catalyst was characterized by SEM, TEM, XRD, FITR, TG, ICP-AES, respectively.Ultimately, the catalytic performance of the supported Pd nanoparticles catalyst was investigated by catalysing the Sonogashira Cross-Coupling Reaction between aryl halides and arylacetylene. Research shows that the novel supported Pd nanoparticles catalyst exhibits very superior catalytic activity in catalysing Sonogashira cross-coupling reaction between aryl halides and arylacetylene even at the absence of the cocatalyst (CuI), and the side reaction to produce by-product (1,3-diyne) can be inhibited effectively. In addition, this supported Pd nanoparticles catalyst exhibites stable recovery and high catalytic activity for it can be effectively reused 8 times without obvious loss of catalytic activity. Especially, the yields of the target products of the Sonogashira cross-coupling reaction between iodobenzene and phenylacetylene, 3-aminophenylacetylene and 4-(ethynyl)phthalic anhydride can reach up to about 79%, 78% and 95% after this novel supported Pd nanoparticles catalyst being used eight times, respectively.

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Synthesis and applications of polymeric N-heterocyclic carbene palladium complex-grafted silica as a novel recyclable nano-catalyst for Heck and Sonogashira coupling reactions

Cited by 65 publications

References 63 publications

Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

Poly(vinylpyridine)‐Grafted Silica Containing Palladium or Nickel Nanoparticles as Heterogeneous Catalysts for the Sonogashira Coupling Reaction

Fabrication of PEI grafted Fe₃O₄/SiO₂/P(GMA-co-EGDMA) nanoparticle anchored palladium nanocatalyst and its application in Sonogashira cross-coupling reactions

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Synthesis and applications of polymeric N-heterocyclic carbene palladium complex-grafted silica as a novel recyclable nano-catalyst for Heck and Sonogashira coupling reactions

Cited by 65 publications

References 63 publications

Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

Poly(vinylpyridine)‐Grafted Silica Containing Palladium or Nickel Nanoparticles as Heterogeneous Catalysts for the Sonogashira Coupling Reaction

Fabrication of PEI grafted Fe3O4/SiO2/P(GMA-co-EGDMA) nanoparticle anchored palladium nanocatalyst and its application in Sonogashira cross-coupling reactions

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Fabrication of PEI grafted Fe₃O₄/SiO₂/P(GMA-co-EGDMA) nanoparticle anchored palladium nanocatalyst and its application in Sonogashira cross-coupling reactions