Heterogeneously Pd/C catalysed procedure for the vinylation of aryl bromides

Joucla, Lionel; Cusati, Giuseppe; Pinel, Catherine; Djakovitch, Laurent

doi:10.1016/j.apcata.2009.03.016

Cited by 31 publications

(20 citation statements)

References 43 publications

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“…[26,27] Such compounds are useful intermediates for the synthesis of stilbenes, an important class of biologically relevant molecules including the wellknown resveratrol and combretastatin A-4. [28,29] Over the past few years, three reports dealing with homogenous Pd-based one-pot strategies, through either Hiyama/Heck [30] or double Heck [31,32] couplings, have emerged from the literature as valuable improvements toward the synthesis of stilbenes.…”

Section: Introductionmentioning

confidence: 99%

One‐Pot Suzuki/Heck Sequence for the Synthesis of (E)‐Stilbenes Featuring a Recyclable Silica‐Supported Palladium Catalyst via a Multi‐Component Reaction in 1,3‐Propanediol

et al. 2010

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Joucla, Lionel Cusati, Giuseppe Pinel, Catherine Djakovitch, LaurentThe synthesis of (E)-stilbenes was performed following a one-pot Suzuki/Heck sequence through the use of potassium vinyltrifluoroborate. The combination of heterogeneous palladium/silica (Pd/SiO2) catalyst with potassium phosphate monohydrate (K3PO4H2O) as base resulted in useful to good isolated yields regardless of the ortho-, meta- or para-substitution of the aryl halides employed. In a sustainable approach. we found that bio-sourced 1,3-propanediol could advantageously replace N-methyl-pyrrolidone (NMP) as similar yields were obtained Moreover, the reactivity gap between aryl iodides and bromides resulting from the use of 1,3-propanediol allowed an efficient multi-component approach toward the synthesis of (E)-stilbenes. Furthermore. this heterogeneous catalyst was found to he extremely robust despite the use of aerobic conditions and was successfully re-used over several cycles

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Section: Introductionmentioning

confidence: 99%

One‐Pot Suzuki/Heck Sequence for the Synthesis of (E)‐Stilbenes Featuring a Recyclable Silica‐Supported Palladium Catalyst via a Multi‐Component Reaction in 1,3‐Propanediol

et al. 2010

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“…These results are consistent with the observation that most heterogeneous catalysts serve as reservoirs of catalytically active species. 9,15,16 Indeed, the Heck reaction proceeded in the used test tube even in the absence of GaAs powder. This is proof of the role of GaAs-Pd as a scaffold 25 (reservoir).…”

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confidence: 99%

“…9,20 However, it has been suggested that the leached palladium 45 particles are the actual active species that accelerate the crosscoupling reactions. 9,15,16 A small amount of palladium dissolves in a solution by complex formation with the aryl halide used in the coupling reaction and re-deposits on the surface of the solid support after the aryl halide is completely consumed. This implies 50 that solid-supported palladium catalysts serve as reservoirs of catalytically active species to effect the C-C bond formations homogeneously.…”

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confidence: 99%

“…Palladium complexes anchored on solid supports [6][7][8][9][10][11][12] or encapsulated in polystyrenes 13 have been 30 successfully synthesized and used in a variety of reactions. Recently, solid-supported Pd(0) nanoparticles have gained importance [14][15][16][17][18][19][20][21][22][23][24] because of their size effect 22-25 as well as air and moisture stability. Another advantage of these catalysts is that they can be synthesized using inexpensive ligands.…”

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confidence: 99%

“…This implies 50 that solid-supported palladium catalysts serve as reservoirs of catalytically active species to effect the C-C bond formations homogeneously. Hence, it is desirable to develop a suitable scaffold that has a moderate affinity for Pd(0) nanoparticles [15][16][17][18][19][20][21]27 and is strong enough to retain and stabilize them without 55 aggregation, but weak enough to release them slowly. Recently, suitable scaffolds with moderate affinity have been developed for surface stabilization of Pd(0) nanoparticles, in which multiple hydroxy groups on the surface serve as ligands to prevent the aggregation of nanoparticles while preserving the 60 catalytic activity.…”

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confidence: 99%

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Hydroxylated surface of GaAs as a scaffold for a heterogeneous Pd catalyst

Nishiwaki

Konishi

Hirao

et al. 2012

Phys. Chem. Chem. Phys.

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A novel use of GaAs, namely, as a scaffold for a heterogeneous palladium catalyst, is proposed. Hydroxy groups on the GaAs surface play important roles. During the adsorption of Pd(OAc) 2 on the GaAs surface, the hydroxy groups attract Pd(II) species by anion exchange. A subsequent redox reaction proceeds to generate Pd(0) nanoparticles, which are stabilized on the GaAs surface. This process is confirmed by 10 surface-sensitive measurements: diffuse reflection IR spectroscopy and X-ray photoelectron spectroscopy. Moreover, a more bulk-sensitive measurement, hard X-ray photoemission spectroscopy with synchrotron radiation, also supported our considerations. The amounts of Pd(0) nanoparticles on the surface were evaluated by catalytic activity, yield, and recyclability in the Heck reaction, in addition to deposit test.

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Palladium on Carbon‐Catalyzed Cross‐Coupling using Triarylbismuths

et al. 2012

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Simple and efficient protocols for the 10% palladium on carbon (Pd/C)-catalyzed crosscoupling reactions between triarylbismuths and aryl halides have been developed. A variety of iodoand bromobenzenes possessing an electron-withdrawing group on the aromatic nucleus were smoothly cross-coupled in the presence of 10% Pd/C, sodium phosphate dodecahydrate (Na 3 PO 4 ·12 H 2 O) and 1,4-diazabicycloA C H T U N G T R E N N U N G [2.2.2]octane (DABCO) in heated N-methyl-2-pyrrolidone (NMP) as the solvent. For the arylations of iodobenzenes, the reactions effectively proceeded under the combined use of caesium fluoride (CsF) and 2,2'-biquinoline. Furthermore, a ligand-free 10% Pd/C-catalyzed cross-coupling reaction between the aryl iodides and triarylbismuths was also established by the addition of tetra-n-buthylammonium fluoride trihydrate (TBAF·3 H 2 O) in which the palladium metals were hardly leached from the catalyst into the reaction media.

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Heterogeneously Pd/C catalysed procedure for the vinylation of aryl bromides

Cited by 31 publications

References 43 publications

One‐Pot Suzuki/Heck Sequence for the Synthesis of (E)‐Stilbenes Featuring a Recyclable Silica‐Supported Palladium Catalyst via a Multi‐Component Reaction in 1,3‐Propanediol

One‐Pot Suzuki/Heck Sequence for the Synthesis of (E)‐Stilbenes Featuring a Recyclable Silica‐Supported Palladium Catalyst via a Multi‐Component Reaction in 1,3‐Propanediol

Hydroxylated surface of GaAs as a scaffold for a heterogeneous Pd catalyst

Palladium on Carbon‐Catalyzed Cross‐Coupling using Triarylbismuths

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