Polymeric Scavenger Reagents in Organic Synthesis

Eames, Jason; Watkinson, Michael

doi:10.1002/1099-0690(200104)2001:7<1213::aid-ejoc1213>3.0.co;2-k

Cited by 97 publications

(42 citation statements)

References 38 publications

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“…Each of these classes, through the help of combinatorial chemistry, have been used in the synthesis of numerous compounds . Scavenging resins are mainly used for the removal of impurities and/or excess reagent in the reaction medium; this has been demonstrated as one of the major advantages of this technique in that the product of the reaction is not impaired since the residuals can be removed from the aqueous or organic solution . This purification technique consists of the capture of a determined component (the nonreacted reagent, impurities, or co‐products) through reaction with a group that is part of the resin, which can then be removed by filtration.…”

Section: Introductionmentioning

confidence: 99%

Production of a low‐cost scavenger resin to capture aldehydes and ketones in solutions

Oliveira

Kartnaller

Pedrosa

et al. 2015

J of Applied Polymer Sci

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Over the past years, polymer-supported reagents have been extensively studied and used in various applications. One class of such reagents is called "scavengers," which can be used to easily eliminate compounds in a solution. The present work describes the production of a resin that can be used for scavenging ketones and aldehydes using low-cost reagents and simple reaction steps, named here Amb15-Iso. This resin is obtained by reacting a low-cost commercial sulfonyl resin, Amberlyst-15, with isoniazid, a drug used for the treatment of tuberculosis. Acetone and isobutyraldehyde were used as carbonyl compound models. The reactions were monitored in-line by ATR-FTIR and results showed that the polarity of the solvent influences the kinetics of the production of the resin and water proved to be the fastest solvent. For the scavenging of acetone and isobutyraldehyde, two factors showed to have an impact in the amount of compounds captured: the polarity of the solvent and the solubility of water in the solvent. The capacity of scavenging acetone in water varied from 0.11 to 0.28 mmol per gram of resin, depending on the initial acetone concentration. The equilibrium of this reaction was modeled and the equilibrium constant was calculated to be 0.63 6 0.07 L mol 21 . The resin was also recycled and tested in a second round of scavenging and results showed that there was not much difference between the new resin and the recycled one, proving that the Amberlyst-15 could be reused for a second cycle of scavenging. V C 2015 Wiley Periodicals, Inc. J.Appl. Polym. Sci. 2015, 132, 42291.

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Section: Introductionmentioning

confidence: 99%

Production of a low‐cost scavenger resin to capture aldehydes and ketones in solutions

Oliveira

Kartnaller

Pedrosa

et al. 2015

J of Applied Polymer Sci

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“…As a result, much recent work has been focused on developing and selection new ligand-derivative polymer supports for attachment of metals and on developing methods for increasing activity and selectivity [10,11]. A polymer-supported N -heterocyclic carbene (NHC) palladium com-plex has been prepared by Herrmann and co-workers [12] by the direct reaction of readily prepared alcohol-functionalized palladium carbene complexes with p-(bromomethyl)phenoxymethyl-functionalized polystyrene using N i Pr 2 Et and CsI as coupling agents.…”

Section: Introductionmentioning

confidence: 99%

Polyimide-Supported Dichloro-1,3-bis(p-dimethylaminobenzyl)benzimidazolidin-2-ilidenruthenium (II) as Effective Catalyst for Hydrosilylation Reactions

Köytepe

Seçki̇n

Yaşar

et al. 2008

Designed Monomers and Polymers

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The present study relates to a heterogeneous polyimide-supported transition metal complex catalyst for hydrosilylation reactions, which is prepared by functionalizing a heat-and acid-resistant polyimide resin with a homogeneous metal catalyst of ruthenium (II) complex. The heterogeneous polyimide-supported transition metal complex catalyst of the invention provides superior catalytic activity, selectivity and stability in the hydrosilylation of acetophenone. Further, the catalyst has strong resistance against heat and acid. Besides, the catalyst of the invention may provide the following advantage which are critical in industrial use: it can be easily separated from the reaction product, which eases recycling of the catalyst.

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“…[52][53][54][55] The covalent binding of catalyst with polymeric support offers a number of advantages over traditional solution-phase chemistry. In an ideal case, the supported catalysts can be recovered from reaction mixtures by simple filtration, they do not contaminate the product solution, they may be recycled, and they can help increase selectivity.…”

Section: Synthesis Organoselenium Compounds Immobilized On Solid Suppmentioning

confidence: 99%

Diaryl diselenides and benzisoselenazol-3(2H)-ones as oxygen-transfer agents

Młochowski¹,

Brzaszcz²,

Chojnacka³

et al. 2004

Arkivoc

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Diaryl diselenides and related benzisoselenazol-3(2H)-ones are presented as the catalyst for hydogen peroxide and t-butylhydroperoxide oxidation of various types of organic substrates. Most of the reactions studied in our laboratory have a practical value. The aromatic aldehydes and ketones are oxidized to arenecarboxylic acids or converted to the phenols while cycloalkanones gave cycloalkanecarboxylic acids with ring contraction. From the azomethine compounds, depending on their structure, nitriles, parent carbonyl compounds, carboxylic acids or their esters are produced. Primary benzylamines gave nitriles, while the secondary are oxidized to nitrones. Alkylarenes are oxidized to the alkylaryl ketones and alkenes to epoxides. By oxidation of 1,4-dimethoxysubstituted and some polycondensed arenes the quinones are produced. The postulated mechanisms are discussed and the methods for synthesis of the title compounds are described.

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Polymeric Scavenger Reagents in Organic Synthesis

Cited by 97 publications

References 38 publications

Production of a low‐cost scavenger resin to capture aldehydes and ketones in solutions

Production of a low‐cost scavenger resin to capture aldehydes and ketones in solutions

Polyimide-Supported Dichloro-1,3-bis(p-dimethylaminobenzyl)benzimidazolidin-2-ilidenruthenium (II) as Effective Catalyst for Hydrosilylation Reactions

Diaryl diselenides and benzisoselenazol-3(2H)-ones as oxygen-transfer agents

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