An Aerobic and Very Fast Pd/C‐Catalyzed Ligand‐Free and Aqueous Suzuki Reaction Under Mild Conditions

Li, Chun; Rao, Xiaofeng; Zhang, Yixia; Li, Xinmin; Qiu, Jieshan; Zhang, Jin

doi:10.1002/ejoc.201300334

Cited by 49 publications

(12 citation statements)

References 77 publications

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“…Several groups have reported its use for Suzuki couplings using generally 10-50 mequiv. of supported palladium 54,55 . It is noteworthy that the activity of the Pd/C catalyst is often dependent on its commercial source 56,57 and that 55 decreases of the yields obtained after several reuses are frequently observed owing to the formation and/or growth of palladium aggregates 58,59 .…”

Section: A Introductionmentioning

confidence: 99%

Biosourced mesoporous carbon with embedded palladium nanoparticles by a one pot soft-template synthesis: application to Suzuki reactions

et al. 2015

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International audienceA simple, direct and environmentally-friendly one-pot preparation of a palladium-containing mesoporous carbon (Pd@MC) from a cheap, non-hazardous and easily accessible biopolymer (tannin) as a carbon precursor, Pluronic (R) F127 surfactant as a pore structuring agent and a palladium salt is reported. This material has the peculiarity to have palladium nanoparticles entrapped in irregular voids connected to the worm-like mesoporous network limiting palladium leaching while keeping good access to the reactants. It was successfully used as a catalyst for ligand-free Suzuki-Miyaura couplings of aryl bromides in a green solvent (propane-1,2-diol) in the presence of extremely low amounts of supported palladium (usually 30 mu equiv.). It is noteworthy that almost palladium-free products (containing less than 1.5 mu equiv. of precious metal) can be obtained. The possibility to reuse the catalyst was also ascertained

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Section: A Introductionmentioning

confidence: 99%

Biosourced mesoporous carbon with embedded palladium nanoparticles by a one pot soft-template synthesis: application to Suzuki reactions

et al. 2015

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“…This latter group further indicated that the oxidative addition of aryl bromides or aryl borates was the main cause for Pd leaching. Further interesting examples of Suzuki–Miyaura reactions catalyzed by Pd/C have been reported, but most developed protocols mainly focus on using active aryl halides, such as aryl iodides and bromides, to obtain non‐heterobiaryl compounds. It is still a challenge, however, to use Pd/C as catalyst for the synthesis of heterocyclic biaryl derivatives.…”

Section: Applications Of Pd/cmentioning

confidence: 99%

Development of the Applications of Palladium on Charcoal in Organic Synthesis

Liu

Astruc

2018

Adv Synth Catal

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Palladium on charcoal( Pd/C)h as lots of salient merits:( i) it is ac heap andc ommercial source of palladium, (ii)i ts hows efficientc atalytic activity even without ligands,( iii)a saheterogeneous catalyst it is easily recycledm any times by simple filtration,a nd (iv) it is applicablet oag reat number of reactions and substrates,a lthough it is eventually less efficient than homogeneous Pd catalysts containing some sophisticated ligands.T hisr eview recalls the main background ands ummarizes the progress made essentially during the last twelve years in Pd/C-catalyzed organic synthesis since the reviews by Felpins group andSekiin2 006.

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“…11 ). In comparison with Pd/C materials 48 49 (entry 17 and 18), Pd@Y-DDQ required less catalyst-loading and showed higher reaction yeilds. The high catalytic activity of Suzuki-Miyaura cross-coupling reaction should be attributed to the exposed and well-dispersed Pd NPs on the MOF support.…”

Section: Resultsmentioning

confidence: 98%

Lanthanide Metal-Organic Frameworks with Six-Coordinated Ln(III) Ions and Free Functional Organic Sites for Adsorptions and Extensive Catalytic Activities

Zhu

et al. 2016

Sci Rep

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Three chelating-amino-functionalized lanthanide metal-organic frameworks, Y-DDQ, Dy-DDQ and Eu-DDQ, were synthesized with a flexible dicarboxylate ligand based on quinoxaline (H2DDQ = N, N′-dibenzoic acid-2,3-diaminoquinoxaline). The three-dimensional framework is constructed by the H2DDQ linkers connecting the zigzag ladders, showing a net of sra topology. In the structures, one kind of Ln(III) ions metal centers are six-coordinated and thus can potentially behave as open metal sites (OMSs), while the free chelating amino groups can act as free functional organic sites (FOSs). The N2 and Ar adsorption behaviors indicate that these Ln-DDQ exhibits stable microporous frameworks with high surface area after remove of the solvents. Owing to presence of OMSs and FOSs, these MOFs show good ability of CO2, dyes captures and Lewis acid catalyst for cyanosilylation reaction. In view of the existing FOSs in the framework, Pd NPs were immobilized onto the MOFs through graft interactions between free chelating amino groups and metal ions precursor using postsynthetic modification. The well dispersed Pd@Ln-DDQs exhibit efficient and recyclable catalytic reduction of 4-nitrophenol to 4-aminophenol, and they can also act as an excellent catalyst for Suzuki-Miyaura cross-coupling reactions with the exposed Pd NPs.

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An Aerobic and Very Fast Pd/C‐Catalyzed Ligand‐Free and Aqueous Suzuki Reaction Under Mild Conditions

Cited by 49 publications

References 77 publications

Biosourced mesoporous carbon with embedded palladium nanoparticles by a one pot soft-template synthesis: application to Suzuki reactions

Biosourced mesoporous carbon with embedded palladium nanoparticles by a one pot soft-template synthesis: application to Suzuki reactions

Development of the Applications of Palladium on Charcoal in Organic Synthesis

Lanthanide Metal-Organic Frameworks with Six-Coordinated Ln(III) Ions and Free Functional Organic Sites for Adsorptions and Extensive Catalytic Activities

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