Combination of Perfluoroalkyl and Triazole Moieties: A New Recovery Strategy for TEMPO

Gheorghe, Alexandru; Chinnusamy, Tamilselvi; Cuevas-Yáñez, Erick; Hilgers, Petra; Reiser, Oliver

doi:10.1021/ol801555f

Cited by 60 publications

(33 citation statements)

References 45 publications

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“…Other highly or moderately fluorinated TEMPO derivatives were prepared and used as readily separable catalysts for the oxidation of various alcohols. [117] The imidazolium salt conjugated TEMPO compound 29 ( Figure 2) was applied as a catalyst for nitroxide-mediated oxidations. [118] The modified TEMPO derivative showed similar catalyst activity as unmodified TEMPO.…”

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confidence: 99%

Nitroxides: Applications in Synthesis and in Polymer Chemistry

2011

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This Review describes the application of nitroxides to synthesis and polymer chemistry. The synthesis and physical properties of nitroxides are discussed first. The largest section focuses on their application as stoichiometric and catalytic oxidants in organic synthesis. The oxidation of alcohols and carbanions, as well as oxidative C-C bond-forming reactions are presented along with other typical oxidative transformations. A section is also dedicated to the extensive use of nitroxides as trapping reagents for C-centered radicals in radical chemistry. Alkoxyamines derived from nitroxides are shown to be highly useful precursors of C-centered radicals in synthesis and also in polymer chemistry. The last section discusses the basics of nitroxide-mediated radical polymerization (NMP) and also highlights new developments in the synthesis of complex polymer architectures.

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confidence: 99%

Nitroxides: Applications in Synthesis and in Polymer Chemistry

2011

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“…Likewise, ligation of 9 with azide 12 [13] furnished the azabis(oxazoline) 13, having three perfluoroalkyl chains and four triazoles incorporated (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Combining Fluorous and Triazole Moieties for the Tagging of Chiral Azabis(oxazoline) Ligands

Rasappan¹,

Olbrich²,

Reiser³

2009

Adv Synth Catal

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New fluorous-tagged azabis(oxazoline) ligands were prepared using the copper-catalyzed azide-alkyne cycloaddition as ligation method. The resulting ligands were tested in copper-catalyzed asymmetric benzoylations (up to 99% ee), nitroaldol (up to 90% ee), and Michael reactions (up to 82% ee). The combination of unpolar fluorinated alkyl chains and polar triazole moieties imposes properties that are beneficial for the catalysts with respect to recyclability and selectivity. The scope and limitation of this strategy in comparison to analogous catalysts immobilized on methoxypolyethylene glycol (MeOPEG) or polystyrene is discussed. Moreover, this study shows that the choice of solvent for a given reaction is crucial to arrive at highly recyclable bis(oxazoline) catalysts.

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“…Weitere Berichte über hochund moderat fluorierte TEMPO-Derivate als wiederverwendbare Katalysatoren für die Alkoholoxidation finden sich in der Literatur. [117] In einer anderen Zweiphasenextrakion konnte das mit einem Imidazoliumsalz konjugierte TEMPO 29 (Abbildung 2) als Katalysator für Nitroxid-vermittelte Oxidationen eingesetzt und anschließend zurückgewonnen werden. [118] Das so modifizierte TEMPO-Derivat zeigte vergleichbare Aktivitäten wie TEMPO selbst.…”

Section: Kinetische Racematspaltung Von Alkoholenunclassified

Nitroxide: Anwendungen in der Synthese und in der Polymerchemie

2011

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Nitroxide werden in der Synthese und in der Polymerchemie verwendet. In diesem Aufsatz werden zunächst Methoden zur Herstellung von Nitroxiden und deren physikalische Eigenschaften besprochen. Der folgende Abschnitt beschreibt die Verwendung von Nitroxiden als stöchiometrische und katalytische Oxidationsmittel in der organischen Synthese. Die Oxidation von Alkoholen und Carbanionen spielt dabei ebenso eine wichtige Rolle wie oxidative C‐C‐Bindungsknüpfungen. Anschließend widmet sich ein Abschnitt der Rolle von Nitroxiden als Abfangreagentien für C‐zentrierte Radikale in der Radikalchemie. Nitroxide, die sich von Alkoxyaminen ableiten, fungieren als nützliche Ausgangsmaterialien für C‐zentrierte Radikale, deren Einsatz in der Synthese und in der Polymerchemie beschrieben wird. Der letzte Abschnitt stellt die Grundlagen der Nitroxid‐vermittelten Polymerisation (NMP) vor und zeigt neuere Entwicklungen beim Design komplexer Polymerarchitekturen auf.

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Combination of Perfluoroalkyl and Triazole Moieties: A New Recovery Strategy for TEMPO

Abstract: The attachment of multiple triazole moieties and perfluoroalkyl chains to TEMPO promotes emulsion formation in dichloromethane/water, giving a highly active and easily recoverable catalyst for the oxidation of alcohols.

Cited by 60 publications

References 45 publications

Nitroxides: Applications in Synthesis and in Polymer Chemistry

Nitroxides: Applications in Synthesis and in Polymer Chemistry

Combining Fluorous and Triazole Moieties for the Tagging of Chiral Azabis(oxazoline) Ligands

Nitroxide: Anwendungen in der Synthese und in der Polymerchemie

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