Assessment of the Reusability of Pd Complexes Supported on Fluorous Silica Gel as Catalysts for Suzuki Couplings

Tzschucke, Carl Christoph; Andrushko, Vasyl; Bannwarth, Willi

doi:10.1002/ejoc.200500281

Cited by 33 publications

(18 citation statements)

References 23 publications

(33 reference statements)

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“…(2)]. [35] In our laboratories, we developed a Pd II precatalyst which was functionalized with an ionic liquid tag resulting in a task specific onium salt (TSOS) 5. [36,37] The tag allows for specific interactions with ionic liquids so that the complex was immobilized both on silica gel (SiO 2 ) according to Mehnerts procedure yielding functionalized solid phase 7 as well as to the newly developed ionic-liquid-type polymer which derives from polyvinyl imidazole (Scheme 3).…”

Section: Concepts Of Combining Enabling Techniquesmentioning

confidence: 99%

Combining Enabling Techniques in Organic Synthesis: Continuous Flow Processes with Heterogenized Catalysts

Kirschning

Solodenko

Mennecke

2006

Chemistry A European J

369

147

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The concepts article describes enabling techniques (solid-phase assisted synthesis, new reactor design, microwave irradiation and new solvents) in organic chemistry and emphasizes the combination of several of them for creating new synthetic technology platforms. Particular focus is put on the combination of immobilized catalysts as well as biocatalysts with continuous flow processes. In this context, the PASSflow continuous flow technique fulfils both chemical as well as chemical engineering requirements. It combines reactor design with optimized, monolithic solid phases as well as reversible immobilization techniques for performing small as well as large scale synthesis with heterogenized catalysts under continuous flow conditions.

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Section: Concepts Of Combining Enabling Techniquesmentioning

confidence: 99%

Combining Enabling Techniques in Organic Synthesis: Continuous Flow Processes with Heterogenized Catalysts

Kirschning

Solodenko

Mennecke

2006

Chemistry A European J

369

147

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“…It is well-known that Pd is effective in catalyzing C-C bond formation reactions [27][28][29][30]. Among palladium-catalyzed couplings, the Suzuki-Miyaura [29], Sonogashira [27] and Heck [28] reactions are the most widely used.…”

Section: Activity For the Heck Reaction Of The Pvbcs-2 Nanospheresmentioning

confidence: 99%

“…Among palladium-catalyzed couplings, the Suzuki-Miyaura [29], Sonogashira [27] and Heck [28] reactions are the most widely used. In this work, the catalytic activity of the PVBCS-2 nanospheres for Heck reaction was investigated using the model reaction of iodobenzene and methyl acrylate ( Figure 6).…”

Section: Activity For the Heck Reaction Of The Pvbcs-2 Nanospheresmentioning

confidence: 99%

“…However, there have been few reports on procedures to graft functional polymer chains onto solid supports and the properties, such as catalytic properties, of the shell modified materials. Palladium is a highly active and selective catalyst in C-C bond formation reactions [27][28][29][30]. However, the problem that concerns many researchers is to combine high efficiency of the catalyst with the possibility of its easy separation from the reaction products.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and property of polymer nanospheres with Pd/P4VP shells via surface RAFT polymerization

Shi¹,

Zhang²,

Zhu³

et al. 2009

Express Polym. Lett.

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Abstract.A reversible addition-fragmentation chain transfer (RAFT) agent with carbazole as Z-group was immobilized on the surfaces of the cross-linked poly (4-vinylbenzyl chloride-co-styrene) (PVBCS) nanospheres with a diameter of about 70 nm by the reaction of benzyl chloride groups in the PVBCS between carbazole and carbon sulfide. Then surface RAFT polymerization of 4-vinylpyridine (4VP) was used to modify the nanospheres to produce a well-defined and covalently tethered P4VP shell. By surface activation in a PdCl2 solution and then reduction by hydrazine hydrate (N2H4·H2O), the P4VP composite shells were obtained containing densely palladium metal nanoparticles. The chemical composition of the nanosphere surfaces at various stages of the surface modification was characterized by X-ray photoelectron spectroscopy (XPS). Transmission electron microscopy (TEM) was used to characterize the morphology of the hybrid nanospheres. The Pd/P4VP shell nanospheres were also applied to the catalytic reaction and proved to be efficient and reusable for the Heck reaction.

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“…Various methods are available for the anchoring of transition metal complexes onto organic or inorganic carriers: including entrapment, adsorption, ion-pair formation and covalent binding. Several examples of non-covalent immobilization on a silica matrix can be cited: the fluorous reversed-phase silica gel described by Bannwarth, [24][25][26] the heterogeneous detergents based on silica gel obtained by Oehme [27] and zeolites containing PdCl 2 studied by Garcia. [28] Nevertheless, the attachment of the metal complex to the support by covalent bond formation provides many advantages over the non-covalent approach, the main one being to reduce leaching and thus palladium contamination of the products.…”

Section: Introductionmentioning

confidence: 99%

Suzuki–Miyaura Reactions of Aryl Chloride Derivatives with Arylboronic Acids using Mesoporous Silica‐Supported Aryldicyclohexylphosphine

et al. 2007

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The Suzuki-Miyaura reactions using mesoporous-supported aryldicyclohexylphosphine as ligand have been investigated. The catalysts were based on SBA-15 type mesoporous silica which was transformed in a four-step synthesis leading to a phosphine-containing hybrid material The most productive catalytic system studied was generated in situ from this material and the homogeneous palladium complex, PdA C H T U N G T R E N N U N G (OAc) 2 . Other catalytic systems were studied for comparison [homogeneous cataysts, a "preformed" catalyst obtained by reaction of PdCl 2A C H T U N G T R E N N U N G (PhCN) 2 and the phosphine-containing material].Variations involving the solvent system, the substrate aryl chloride and the arylboronic acid reactant were also studied. For both in situ and preformed catalyst systems, high conversions and yields are obtained for activated aryl chlorides. Success of the reaction for unactivated aryl chlorides was limited to the catalyst formed in situ. The catalyst formed in situ was also shown to be reactive under aqueous reaction conditions in the cross-coupling of 1-(4-chlorophenyl)ethanone with phenylboronic acid.

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Assessment of the Reusability of Pd Complexes Supported on Fluorous Silica Gel as Catalysts for Suzuki Couplings

Cited by 33 publications

References 23 publications

Combining Enabling Techniques in Organic Synthesis: Continuous Flow Processes with Heterogenized Catalysts

Combining Enabling Techniques in Organic Synthesis: Continuous Flow Processes with Heterogenized Catalysts

Synthesis and property of polymer nanospheres with Pd/P4VP shells via surface RAFT polymerization

Suzuki–Miyaura Reactions of Aryl Chloride Derivatives with Arylboronic Acids using Mesoporous Silica‐Supported Aryldicyclohexylphosphine

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