Functional resins in palladium catalysis: promising materials for Heck reaction in aprotic polar solvents

Caporusso, Anna Maria; Innocenti, P.; Aronica, Laura Antonella; Vitulli, Giovanni; Gallina, R.; Biffis, Andrea; Zecca, Marco; Corain, Benedetto

doi:10.1016/j.jcat.2005.05.008

Cited by 61 publications

(36 citation statements)

References 33 publications

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“…Several supports were used to immobilise palladium complexes or to support palladium particles for the Heck reaction: ligand-protected palladium nanoparticles, [43][44][45][46][47][48][49] palladium on active carbon [50][51][52][53] or carbon nanotubes, [54] palladium on metal oxides [27,[55][56][57][58][59][60][61][62][63][64][65][66][67][68][69][70][71][72][73][74] or palladium on functional polymers. [75][76][77][78][79] Among them the zeolites showed exceptional activity and stability. [62,69,70,73] Most of the work reported in this area concerned mainly model reactions, reacting aryl iodides and bromides with styrene or acrylates.…”

Section: Introductionmentioning

confidence: 99%

Efficient Heterogeneously Palladium‐Catalysed Heck Arylation of Acrolein Diethyl Acetal. Selective Synthesis of Cinnamaldehydes or 3‐Arylpropionic Esters

et al. 2007

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) 4 ]/NaY} catalyst was applied successfully to the Heck arylation of acrolein diethyl acetal using a large variety of aryl and heteroaryl bromides. Depending on the reaction conditions (Heck versus Cacchi) good to high selectivities toward the 3-arylpropionic esters or to the cinnamaldehydes were achieved, respectively. Under classical Heck conditions, while the catalyst was found to be stable over the two first runs, it showed significant loss of activity from the third cycle. Under Cacchi conditions, the catalyst could not be reused as it led to high dehalogenation rates. All results indicate that the reactions proceed through dissolved palladium species in the bulk solution (leaching). As observed by transmission electronic microscopic (TEM) analyses, while these species can be trapped and stabilised by the zeolite framework under the Heck conditions, they tend to form large palladium(0) aggregates under the Cacchi conditions leading to dehalogenation rather than to the expected Heck coupling.

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Section: Introductionmentioning

confidence: 99%

Efficient Heterogeneously Palladium‐Catalysed Heck Arylation of Acrolein Diethyl Acetal. Selective Synthesis of Cinnamaldehydes or 3‐Arylpropionic Esters

et al. 2007

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“…This limitation is common to other reported efforts toward the development of continuous flow systems for Pd-catalyzed C-C bond formation [36,37]. All of them require the use of conventional organic solvents either for the reaction or for the extraction of the product.…”

Section: Catalytic Systems Based On M-sillpsmentioning

confidence: 98%

Development of efficient processes under flow conditions based on catalysts immobilized onto monolithic supported ionic liquid-like phases

Burguete

García‐Verdugo

Karbass

et al. 2009

Pure and Applied Chemistry

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The introduction of imidazolium subunits into polystyrene-divinylbenzene (PS-DVB) polymers enables the preparation of a variety of catalytic systems. Those include the stabilization of catalytically active Pd nanoparticles (PdNPs), immobilized enzymes, and basic catalysts. The use of monolithic supports having the appropriate morphological properties is greatly advantageous for the development of efficient catalytic processes under flow conditions based on those systems. On the other hand, the combination of those supported catalytic systems and flow conditions can be further implemented, in terms of green chemistry, by the substitution of the use of traditional solvents by environmentally friendly conditions such as the use of supercritical fluids (SCFs).

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“…Similar Pd catalysts were applied to Suzuki coupling reactions, giving moderate to high yields in reactions with aryl bromides [22] . Recently, Biffi s and coworkers reported the preparation of Pd nanoparticles stabilised by crosslinked functional organic resins containing tertiary amino, cyano, carboxyl and pyridyl groups, by immobilisation of the palladium precursor followed by chemical reduction or by metal vapor deposition [23] . The catalysts showed moderate to high activity for the coupling reaction of iodobenzene with methyl acrylate; the chemical yields depending on the nature of the stabiliser and the reaction temperature.…”

Section: Stable Palladium Colloids and Nanoparticles 305mentioning

confidence: 99%

The Role of Palladium Nanoparticles as Catalysts for Carbon–Carbon Coupling Reactions

Djakovitch¹,

Köhler²,

Vries³

2007

Nanoparticles and Catalysis

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Functional resins in palladium catalysis: promising materials for Heck reaction in aprotic polar solvents

Cited by 61 publications

References 33 publications

Efficient Heterogeneously Palladium‐Catalysed Heck Arylation of Acrolein Diethyl Acetal. Selective Synthesis of Cinnamaldehydes or 3‐Arylpropionic Esters

Efficient Heterogeneously Palladium‐Catalysed Heck Arylation of Acrolein Diethyl Acetal. Selective Synthesis of Cinnamaldehydes or 3‐Arylpropionic Esters

Development of efficient processes under flow conditions based on catalysts immobilized onto monolithic supported ionic liquid-like phases

The Role of Palladium Nanoparticles as Catalysts for Carbon–Carbon Coupling Reactions

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