Pd catalysts immobilized onto gel-supported ionic liquid-like phases (g-SILLPs): A remarkable effect of the nature of the support

Burguete, M. Isabel; García‐Verdugo, Eduardo; Garcia-Villar, Ignacio; Gelat, Fabien; Licence, Peter; Luis, Santiago V.; Sans, Víctor

doi:10.1016/j.jcat.2009.11.002

Cited by 112 publications

(69 citation statements)

References 78 publications

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“…The practical viability of the palladium-poly(ionic liquid) catalyst membranes in the present study has been demonstrated for the Suzuki--Miyaura coupling reaction of iodobenzene. The measured TOF value of 3097 ± 323 h −1 for heated (343 K) batch reaction mode is comparable with previously reported homogeneous ionic liquid catalysts (TOFs of 10 The palladium membrane loadings used for the Suzuki-Miyaura coupling reaction (a reaction solution equivalent of 0.061 ± 0.004 mol % or 11.1 ± 8 ppm on a mass basis) are lower than most previously reported ionic liquid catalysts (homogeneous and heterogeneous) which range between 0.1-18 mol% [5,[7][8][9][10][11][12][14][15][16]22,64]. A palladium leaching value of 83 ppb h −1 cm −3 at 343 K compares favourably with previously reported solid support heterogeneous catalysts (where palladium leaching rates exceed 100 ppb h −1 cm −3 ) [65,66].…”

Section: Discussionsupporting

confidence: 81%

Palladium–poly(ionic liquid) membranes for permselective sonochemical flow catalysis

Wilson

Kore

Ritchie

et al. 2018

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-pro t purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. G R A P H I C A L A B S T R A C T A R T I C L E I N F O Keywords:Catalyst membrane Ionic liquid Palladium catalyst Plasmachemical functionalization A B S T R A C TAnisotropic palladium-poly(ionic liquid) catalyst membranes have been prepared by complexation of palladium (II) chloride to poly(ionic liquid) functionalised flexible porous substrates. The practical viability of these low loading (sub 0.1 mol%) palladium catalyst membranes for continuous flow reactions at ambient temperature is demonstrated for the Suzuki-Miyaura carbon-carbon coupling reaction by contacting the reactant mixture with the catalyst membrane and applying sonication. The Suzuki-Miyaura carbon-carbon coupling reaction proceeds at the palladium-poly(ionic liquid) catalyst membrane surface in conjunction with selective permeation (separation) of the desired product species through the underlying porous support. These palladium-poly(ionic liquid) catalyst membranes display minimal metal leaching enabling them to be reused multiple times.

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Section: Discussionsupporting

confidence: 81%

Palladium–poly(ionic liquid) membranes for permselective sonochemical flow catalysis

Wilson

Kore

Ritchie

et al. 2018

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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“…In recent years SILLP (supported ionic liquid-like phase)-based materials prepared by covalent attachment have been synthesized [18,19]. The preference for heterogeneous catalytic systems based on SILLP compared to the corresponding homogeneous ionic liquid phase is motivated by the advantage of easy separation and the ability to use fixed-bed reactors.…”

Section: Introductionmentioning

confidence: 99%

Eco-friendly functionalization of natural halloysite clay nanotube with ionic liquids by microwave irradiation for Suzuki coupling reaction

Massaro

Riela

Cavallaro

et al. 2014

Journal of Organometallic Chemistry

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“…43,88 Poly(norbornene)-supported catalyst showed high activity comparable to the nonsupported analogues. 45 Moreover, the silylated PdNHC complexes 134 and 135 were immobilized on hybrid silicas, producing recyclable catalysts, which have been tested in the copper-free Sonogashira reaction between 4-bromoacetophenone and phenylacetylene with a 0.2 mol % of palladium loading.…”

Section: ç Sonogashira Reactionmentioning

confidence: 97%

“…40 Moreover, the preparation of a bis[(tridecafluorooctyl)imidazol-2-ylidene]palladium complex with a pyridine ligand, 41 and its use in the MizorokiHeck reaction of 4-iodotoluene and 1-octene have been described. 42 New polymeric materials containing imidazolium moieties have been synthesized via a modification of commercially available Merrifield resin, 43 or polyisobutylene (PIB) oligomers 44 by reaction with imidazole derivatives. These functionalized polymers have been employed in the preparation of NHCpalladium-supported materials, which effectively catalyzed the MizorokiHeck reaction.…”

Section: ç Mizoroki-heck Reactionmentioning

confidence: 99%

Heterocyclic Carbene–Metal-catalyzed Csp2–Csp2 and Csp–Csp2 Couplings Using Nonmetallic Substrates

Yus¹,

Pastor²

2013

Chemistry Letters

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The use of carbene ligands for transition-metal complexes has been developed in the last decades, being of special interest those carbenes derived from a nitrogen-containing heterocyclic system. An interesting variety of carbenemetal complexes has been tested in the MizorokiHeck reaction. In comparison, few examples can be found for the MatsudaHeck version of this coupling reaction. Additionally, the Sonogashira coupling has been also catalyzed with different carbenemetal catalysts. Ç IntroductionN-Heterocyclic carbenes (NHCs) have emerged in the last years as a new family of ligands with interesting electronic and structural properties.1 The combination of their strong ·-donor and poor ³-acceptor abilities results in good coordination stability and versatility. Consequently, the use of NHC ligands based on imidazolium ions and related heterocycles has appeared as an alternative to phosphanes in the design of new organometallic catalysts.2 One of the main advantages of employing NHC-based catalysts compared with phosphanebased ones is that they are far less prone to oxidation, allowing their prolonged use, and reuse. Although NHCs were presented as simple tertiary phophane mimics, they have been recognized as much more over the past decade. Therefore, NHC ligands have become an interesting alternative to other types of ligands in different cross-coupling catalytic reactions mediated by transition metals.3 Moreover, the easy introduction of chiral elements in the corresponding precursors have made chiral NHCs promising chiral ligands in metal-based asymmetric catalysis. 4 The comparison between phosphane and NHC ligands, from a mechanistic point of view, has been studied, clear differences being found.5 First, the possibility of carbene ligand dissociation is greatly reduced due to its stronger donor ability; and second, the reactivity of the NHCmetal complex is higher probably caused by the lack of back-donation from the metal to the carbene ligand. Jutand and co-workers studied the reactivity of monocarbene and bis(carbene) Pd(0) complexes toward the oxidative addition of aryl halides, concluding that the electronic and steric properties of the carbene ligand are important factors in this step of the catalytic process. 6 Among the carboncarbon coupling reactions, the activation of a CH from an alkene (MizorokiHeck reaction) or an alkyne (Sonogashira reaction) are of special interest. This highlight review describes the progress on the topic of NHC ligands for transition-metal-catalyzed coupling reactions, employing nonmetallic reagents. Thus, both different NHC precursors and NHCmetal complexes with catalytic activity in the Mizoroki Heck, MatsudaHeck, and Sonogashira reactions are compiled. Ç Mizoroki-Heck ReactionIn 1995, Herrmann and co-workers introduced the use of bis(NHC)Pd complexes as catalysts with long-term stability in the MizorokiHeck reaction.7 Indeed, the carbenes derived from imidazole stabilized the palladium complexes due to their pronounced donor properties, being more stable toward...

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Pd catalysts immobilized onto gel-supported ionic liquid-like phases (g-SILLPs): A remarkable effect of the nature of the support

Cited by 112 publications

References 78 publications

Palladium–poly(ionic liquid) membranes for permselective sonochemical flow catalysis

Palladium–poly(ionic liquid) membranes for permselective sonochemical flow catalysis

Eco-friendly functionalization of natural halloysite clay nanotube with ionic liquids by microwave irradiation for Suzuki coupling reaction

Heterocyclic Carbene–Metal-catalyzed Csp2–Csp2 and Csp–Csp2 Couplings Using Nonmetallic Substrates

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