Supported palladium catalysis using a heteroleptic 2-methylthiomethylpyridine–N,S–donor motif for Mizoroki–Heck and Suzuki–Miyaura coupling, including continuous organic monolith in capillary microscale flow-through mode

Jones, Roderick C.; Canty, Allan J.; Deverell, Jeremy A.; Gardiner, Michael G.; Guijt, Rosanne M.; Rodemann, Thomas; Smith, Jason A.; Tolhurst, Vicki‐Anne

doi:10.1016/j.tet.2009.07.013

Cited by 45 publications

(23 citation statements)

References 55 publications

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“…This is comparable with previously reported Suzuki-Miyaura flow reactors (TOF 10 1 to 10 4 h −1 ) [24,[26][27][28]67], however such systems require high pressures or elevated temperatures. The beneficial preferential separation of iodobenzene reactant and biphenyl product from the phenylboronic acid and reaction solvents in the present study can be ascribed to the selective solubility of the prepared membrane system, Scheme 3.…”

Section: Discussionsupporting

confidence: 90%

“…Despite such heterogeneous systems displaying reduced palladium leaching compared to conventional Pd/C systems, elevated temperatures or microwave heating are still needed to achieve high product yields. Microchannel and capillary reactors are alternatives to packed bed reactor systems, benefiting from lower loadings, high turnover frequencies (TOFs), and low levels of catalyst leaching [26,27]. Their drawback is the small active catalytic areas available in such devices limiting the overall reaction product capacity compared to conventional larger-scale packed bed flow reactors.…”

Section: Introductionmentioning

confidence: 99%

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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: 90%

Section: Introductionmentioning

confidence: 99%

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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“…For catalytic reactions, this issue has been resolved by immobilizing catalytic particles in packed beds [9][10][11] or by coating microstructured features with a catalyst [12]. We have recently reported the use of organic polymer monoliths as a solid support in capillaries and microchips for continuous-flow Suzuki-Miyaura's, Sonogashira and Heck reactions with low leaching of palladium [13][14][15][16]. A monolith is a single macroporous polymer structure.…”

Section: Introductionmentioning

confidence: 99%

UV initiated formation of polymer monoliths in glass and polymer microreactors

Deverell

Rodemann

Smith

et al. 2011

Sensors and Actuators B: Chemical

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“…Its synthesis was based on key steps starting from a Boekelheide reaction 28,29 and followed by an oxidation to the corresponding aldehyde. 30 Treatment with hydroxylamine hydrochloride yielded the oxime 17.…”

Section: 27mentioning

confidence: 99%

Human carbonic anhydrase II as host protein for the creation of artificial metalloenzymes: the asymmetric transfer hydrogenation of imines

et al. 2013

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In the presence of human carbonic anhydrase II, aryl-sulfonamide-bearing IrCp* pianostool complexes catalyze the asymmetric transfer hydrogenation of imines. Critical cofactor-protein interactions revealed by the X-ray structure of [(h 5 -Cp*)Ir(pico 4)Cl] 9 3 WT hCA II were genetically optimized to improve the catalytic performance of the artificial metalloenzyme (68% ee, k cat /K M 6.11 Â 10 À3 min À1 mM À1).

show abstract

Supported palladium catalysis using a heteroleptic 2-methylthiomethylpyridine–N,S–donor motif for Mizoroki–Heck and Suzuki–Miyaura coupling, including continuous organic monolith in capillary microscale flow-through mode

Cited by 45 publications

References 55 publications

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

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

UV initiated formation of polymer monoliths in glass and polymer microreactors

Human carbonic anhydrase II as host protein for the creation of artificial metalloenzymes: the asymmetric transfer hydrogenation of imines

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