Suzuki and Heck reactions catalyzed by preformed palladium clusters and bimetallic clusters

Reetz, Manfred T.; Breinbauer, Rolf; Wanninger, Klaus

doi:10.1016/0040-4039(96)00924-0

Cited by 332 publications

(132 citation statements)

References 37 publications

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“…[1][2][3][4] Usually, carbon-carbon coupling reactions are catalyzed by palladium compound [5][6][7] or Ni-Pd bimetallic catalysts. [8][9][10][11][12][13] On the other hand, the Ni catalysts have many advantages over the Pd catalyst, for example, they are more reactive and often cheaper than the Pd complexes. 14,15 Ni catalyzed reactions are more specific and are complementary to their Pd analogues.…”

Section: Introductionmentioning

confidence: 99%

Suzuki-Miyaura Cross-coupling Reaction Catalyzed by Nickel Nanoparticles Supported on Poly(N-vinyl-2-pyrrolidone)/TiO₂-ZrO₂Composite

Kalbasi¹,

Mosaddegh²

2011

Bulletin of the Korean Chemical Society

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Nickel nanoparticle-poly(N-vinyl-2-pyrrolidone)/TiO 2 -ZrO 2 composite (Ni-PVP/TiO 2 -ZrO 2 ) was prepared by in situ polymerization method. The physical and chemical properties of Ni-PVP/TiO 2 -ZrO 2 were investigated by XRD, FT-IR, BET, TGA, SEM and TEM techniques. The catalytic performance of this novel heterogeneous catalyst was determined for the Suzuki-Miyaura cross-coupling reaction between aryl halides and phenylboronic acid in the presence of methanol-water mixture as solvent. The effects of reaction temperature, the amount of catalyst, amount of support, solvent, and amount of metal for the synthesis of Ni-PVP/TiO 2 -ZrO 2 , were investigated as well as recyclability of the heterogeneous composite. The catalyst used for this synthetically useful transformation showed considerable level of reusability besides very good activity.

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Section: Introductionmentioning

confidence: 99%

Suzuki-Miyaura Cross-coupling Reaction Catalyzed by Nickel Nanoparticles Supported on Poly(N-vinyl-2-pyrrolidone)/TiO₂-ZrO₂Composite

Kalbasi¹,

Mosaddegh²

2011

Bulletin of the Korean Chemical Society

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“…It is also possible to use heterogeneous palladium catalysts such as Pd/C (24). Palladium clusters have also shown to be active (25); in fact Pd-clusters seem to form in most phosphine free Heck reactions. There is an ongoing debate whether the clusters themselves are catalytically active or if it is a monomeric soluble form of Pd that is the active catalyst (10i, 26).…”

Section: The Heck Reactionmentioning

confidence: 99%

The Heck reaction in the production of fine chemicals

2001

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Abstract. An overview is given of the use of the Heck reaction for the production of fine chemicals. Five commercial products have been identified that are produced on a scale in excess of 1 ton/year. The herbicide Prosulfuron™ is produced via a Matsuda reaction of 2-sulfonatobenzenediazonium on 3,3,3-trifluoropropene. The sunscreen agent 2-ethylhexyl p-methoxy-cinnamate has been produced on pilot scale using Pd/C as catalyst. Naproxen™ is produced via the Heck reaction of 2-bromo-6-methoxy-naphthalene on ethylene, followed by carbonylation of the product. Monomers for coatings are produced via a Heck reaction on 2-bromo-benzocyclobutene. A key step in the production of the antiasthma agent Singulair™ is the use of the Heck reaction of methyl 2-iodo-benzoate on allylic alcohol (18) to give ketone (20). The high cost of palladium has spurred much research aimed at the development of more active palladium catalysts. Ligandless catalysts are very attractive for production, but work only on reactive substrates. Palladacycles are much more stable than Pd-phosphine complexes and can be used at higher temperatures. The same effect has been reached with pincer ligands. Bulky ligands lead to coordinatively unsaturated Pd-complexes, which are highly active for the Heck reaction. Recycle of palladium catalysts is also very important to reduce cost. Immobilization of catalysts by attaching ligands to solid support is not very useful, because of leaching and reduced activity. In ligandless Heck reactions the catalyst can be precipitated on carriers such as silica, dicalite, or celite. This material can be restored to its original activity by treatment with I 2 or Br 2 .Key words: homogeneous catalysis, palladium, arylation, olefination, ligandless, catalyst recycle.Résumé : On présente une revue de l'utilisation de la réaction de Heck dans la production de produits chimiques fins. On a identifié cinq produits commerciaux qui sont produits sur une échelle supérieure à une tonne par année. L'herbicide Prosulfuron ® est produit par le biais d'une réaction de Matsuda du 2-sulfonatobenzènediazonium sur le 3,3,3-trifluoropropène. L'agent solaire 4-méthoxycinnamate de 2-éthylhexyle a été produit à l'échelle pilote à l'aide d'un catalyseur de Pd/C. Le Naproxen ® est produit par le biais d'une réaction de Heck du 2-bormo-6-méthoxynaphtalène sur l'éthylène, suivie d'une carbonylation du produit. Des monomères de couches protectrices sont produits par le biais d'une réaction de Heck sur le 2-bromobenzocyclobutène. Une étape clé dans la production de l'agent antiasthmatique Singulair ® est l'utilisation de la réaction de Heck du 2-iodobenzoate de méthyle sur l'alcool allylique 18 pour obtenir la cétone 20. Le prix élevé du palladium a provoqué beaucoup de recherches dans le but de dé-velopper des catalyseurs du palladium qui soient plus actifs. Les catalyseurs sans ligands sont très attrayants pour la production, mais ils ne sont utiles qu'avec des substrats réactifs. Les cycles palladiés sont beaucoup plus stables que les complexes Pd/...

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“…Plasmon absorption for silver colloids was observed at about 402 nm [19], as a result, the bimetallic colloids were expected to equally show single peak absorption band. Therefore, a homogeneous Co or Ni shell layer covering the Ag particles or vice versa can be formed without independent silver particles in the medium, and the Pd and Pt in conjunction with Ag species formed alloy morphological structures [20].…”

Section: Optical Properties Of Ag/m Solsmentioning

confidence: 99%

Polyol mediated hexadecylamine capped silver allied nanobimetallic particles and their fluxional properties

Adekoya

Dare

Mesubi

et al. 2015

Journal of Physics and Chemistry of Solids

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This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting galley proof before it is published in its final citable form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. AbstractThe syntheses of hexadecylamine seed mediated Ag/M(M = Co, Ni, Pd and Pt) allied nanobimetallic particles were successfully carried out by the successive reduction of ligand capped metal ions with polyols, resulting in concomitant precipitation of some high index faceted hybrid Ag/M bimetal nanoparticles. The optical measurements revealed the existence of surface plasmon band and peak broadening that causes diffusion processes of the metal sols to decrease making it possible to monitor the changes spectrophotometrically. The bimetallic nanoparticles were characterized by X-ray diffraction, X-ray photoelectron spectroscopy and electron microscopy techniques which confirm the formation of alloyed clusters.

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Suzuki and Heck reactions catalyzed by preformed palladium clusters and bimetallic clusters

Cited by 332 publications

References 37 publications

Suzuki-Miyaura Cross-coupling Reaction Catalyzed by Nickel Nanoparticles Supported on Poly(N-vinyl-2-pyrrolidone)/TiO₂-ZrO₂Composite

Suzuki-Miyaura Cross-coupling Reaction Catalyzed by Nickel Nanoparticles Supported on Poly(N-vinyl-2-pyrrolidone)/TiO₂-ZrO₂Composite

The Heck reaction in the production of fine chemicals

Polyol mediated hexadecylamine capped silver allied nanobimetallic particles and their fluxional properties

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Suzuki and Heck reactions catalyzed by preformed palladium clusters and bimetallic clusters

Cited by 332 publications

References 37 publications

Suzuki-Miyaura Cross-coupling Reaction Catalyzed by Nickel Nanoparticles Supported on Poly(N-vinyl-2-pyrrolidone)/TiO2-ZrO2Composite

Suzuki-Miyaura Cross-coupling Reaction Catalyzed by Nickel Nanoparticles Supported on Poly(N-vinyl-2-pyrrolidone)/TiO2-ZrO2Composite

The Heck reaction in the production of fine chemicals

Polyol mediated hexadecylamine capped silver allied nanobimetallic particles and their fluxional properties

Contact Info

Product

Resources

About

Suzuki-Miyaura Cross-coupling Reaction Catalyzed by Nickel Nanoparticles Supported on Poly(N-vinyl-2-pyrrolidone)/TiO₂-ZrO₂Composite

Suzuki-Miyaura Cross-coupling Reaction Catalyzed by Nickel Nanoparticles Supported on Poly(N-vinyl-2-pyrrolidone)/TiO₂-ZrO₂Composite