Synthesis of heterogeneous palladium catalyst assemblies by molecular imprinting

Cammidge, Andrew N.; Baines, Nicholas J.; Bellingham, Richard K.

doi:10.1039/b108464j

Cited by 67 publications

(31 citation statements)

References 7 publications

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“…A number of metal centres have been used in these MIP catalysts, including palladium, platinum and rhodium. 1455 Cammidge et al 1456 used polymerizable triphenylphosphine ligands to fix palladium species in a cis geometry for catalysis of Suzuki and Stille coupling reactions. The imprinted palladium catalysts were found to be as active and selective, or more so, than homogeneous systems, a fact attributed to the incorporation of palladium(II) as its (bis(4-ethenylphenyl)diphenylphosphine)-1,2-dihydroxybenzene complex in a cis square planar geometry.…”

Section: Imprinted Polymer Metalloenzyme Mimicsmentioning

confidence: 99%

Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003

Andersson²,

et al. 2006

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Over 1450 references to original papers, reviews and monographs have herein been collected to document the development of molecular imprinting science and technology from the serendipitous discovery of Polyakov in 1931 to recent attempts to implement and understand the principles underlying the technique and its use in a range of application areas. In the presentation of the assembled references, a section presenting reviews and monographs covering the area is followed by papers dealing with fundamental aspects of molecular imprinting and the development of novel polymer formats. Thereafter, literature describing attempts to apply these polymeric materials to a range of application areas is presented.

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Section: Imprinted Polymer Metalloenzyme Mimicsmentioning

confidence: 99%

Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003

Andersson²,

et al. 2006

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“…Most of the data reported in the literature concern bond breakage, in particular hydrolytic reactions with activated substrates. The only examples of catalytic C À C bond formation by imprinted polymers are a Diels-Alder condensation, [4] a Pd-catalysed cross-coupling reaction, [5] an example of class II aldolase [6] and a dimerisation by a peroxidase-like polymer. [7] The development of catalytic microgels, first reported by Resmini et al [8,9] and subsequently by Wulff and his group, [10] represented a significant advance in the field of Abstract: The molecular-imprinting approach was used to obtain a nanogel preparation capable of catalysing the cross-aldol reaction between 4-nitrobenzaldehyde and acetone.…”

Section: Introductionmentioning

confidence: 99%

The First Example of Molecularly Imprinted Nanogels with Aldolase Type I Activity

Carboni

Flavin

Servant

et al. 2008

Chemistry A European J

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The molecular-imprinting approach was used to obtain a nanogel preparation capable of catalysing the cross-aldol reaction between 4-nitrobenzaldehyde and acetone. A polymerisable proline derivative was used as the functional monomer to mimic the enamine-based mechanism of aldolase type I enzymes. The diketone template used to create the cavity was designed to imitate the intermediate of the aldol reaction and was bound to the functional monomer using a reversible covalent interaction prior to polymerisation. By using a high-dilution polymerisation method, soluble imprinted nanogels were prepared with dimensions similar to those of an enzyme and with the advantage of solubility and flexibility previously unattainable with monolithic polymers. Following template removal and estimation of active-site concentrations, the kinetic characterisation of both imprinted and non-imprinted nanogels was carried out with catalyst concentrations between 0.7 and 3.5 mol %. Imprinted nanogel AS147 was found to have a k(cat) value of 0.25 x 10(-2) min(-1), the highest value ever achieved with imprinted polymers catalysing C--C bond formation. Comparison of the catalytic constants for both imprinted nanogel AS147 and non-imprinted nanogel AS133 gave a ratio of k(cat 147)/k(cat 133)=18.8, which is indicative of good imprinting efficiency and highlights the significance of the template during the imprinting process. This work represents a significant demonstration of the superiority of nanogels, when the molecular-imprinting approach is used, over "bulk" polymers for the generation of catalysts.

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“…The catalytic activity of PdAS for the heterogeneous Suzuki-Miyaura reaction [76][77][78][79][80][81][82][83][84][85][86][87][88][89] was investigated (Table 5). Since "water" is the most safe, non-toxic, and easily available solvent, numerous attempts have been made in utilizing it to the organic reactions.…”

Section: Catalytic Activity Of Pdas For the Suzukimiyaura Reactionmentioning

confidence: 99%

Self-Assembled Complexes of Non-cross-linked Amphiphilic Polymeric Ligands with Inorganic Species: Highly Active and Reusable Solid-Phase Polymeric Catalysts

Yamada

2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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IntroductionDevelopment of immobilized and insoluble metal catalysts is of great interest in recent organic chemistry. [1][2][3][4][5][6][7][8][9] The simple recovery of catalysts by filtration and their reuses resulted in enhancing the economical evaluation of the reaction. At the same time, there is a prospect that the environmental pollution caused by residual metals in the waste fluid will be decreased. Although a great deal of effort has been made to carry out such ideal reactions using immobilized metal catalysts, what seems to be lacking is the efficiency of the catalytic systems. It is obvious that the heterogeneous catalytic systems exhibit generally lower activity than the homogeneous ones. Besides, it is expected that the activity of the catalysts decreases gradually in the recycled systems because the metal species leaches away from their supports. Taking these into consideration, we decided to concentrate on developing insoluble metal catalysts which are highly active and stable. We designed that they were still effective in the use of ppm mol eq, and in the recycled use of many times in any reaction media. To achieve the challenging theme, we have focused on the amphiphilic insoluble catalysts based on a novel concept (Chart 1).Over the past few decades, a considerable numbers of study have been made on solid-phase catalysts which were immobilized with cross-linked polystyrene resins, silica gels or metals. These catalytic systems, however, generally resulted in lower catalytic activity compared with their soluble counterparts, and were often obliged to use hazardous chlorohydrocarbon solvents. [10][11][12][13][14][15] Besides, reuse of these catalysts was often difficult owing to the gradual decline of the catalytic activity. These problems made them less practical.In traditional triphase catalysts, as I have mentioned before, a catalytic species was anchored to a linker that was immobilized to a polymer resin or silica gel (Chart 1, above). In July 2005Chem. Pharm. Bull. 53(7) 723-739 (2005)

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Synthesis of heterogeneous palladium catalyst assemblies by molecular imprinting

Cited by 67 publications

References 7 publications

Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003

Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003

The First Example of Molecularly Imprinted Nanogels with Aldolase Type I Activity

Self-Assembled Complexes of Non-cross-linked Amphiphilic Polymeric Ligands with Inorganic Species: Highly Active and Reusable Solid-Phase Polymeric Catalysts

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