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  Sulfonic Acid-Catalyzed Autoxidative Carbon-Carbon Coupling Reaction under Elevated Partial Pressure of Oxygen

Pintér, Á., & Klußmann, M. (2012). Sulfonic Acid-Catalyzed Autoxidative Carbon-Carbon Coupling Reaction under Elevated Partial Pressure of Oxygen. Advanced Synthesis and Catalysis, (354), 701-711. doi:10.1002/adsc.201100563.

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 Urheber:
Pintér, Áron1, Autor           
Klußmann, Martin1, Autor           
Affiliations:
1Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, DE, ou_1445608              

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Schlagwörter: autoxidation; Bronsted acid catalysis; C?C coupling; C?H activation; high-pressure chemistry; oxygen
 Zusammenfassung: An aerobic organocatalytic oxidative CC bond formation reaction of benzylic CH bonds with various C-nucleophiles is described. The coupling reaction proceeds by simply stirring the substrates under elevated partial pressure of oxygen in the presence of a sulfonic acid catalyst at room temperature. Elevation of the pressure enables the reaction of a broad scope of nucleophile substrates otherwise showing poor reactivity at ambient pressure. The benzylic CH bonds of xanthene, acridanes, isochromane and related heterocycles could be functionalized with nucleophiles including ketones, 1,3-dicarbonyl compounds and aldehydes. Electron-rich arenes could be utilized as nucleophiles at elevated temperatures. The reactions are believed to proceed via autoxidation of the benzylic CH bonds to the hydroperoxides and subsequent nucleophilic substitution catalyzed by sulfonic acids.

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 Datum: 2012-03-02
 Publikationsstatus: Erschienen
 Seiten: -
 Ort, Verlag, Ausgabe: -
 Inhaltsverzeichnis: -
 Art der Begutachtung: Expertenbegutachtung
 Identifikatoren: DOI: 10.1002/adsc.201100563
 Art des Abschluß: -

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Titel: Advanced Synthesis and Catalysis
Genre der Quelle: Zeitschrift
 Urheber:
Affiliations:
Ort, Verlag, Ausgabe: Weinheim, Fed. Rep. of Germany : Wiley-VCH Verlag GmbH
Seiten: - Band / Heft: (354) Artikelnummer: - Start- / Endseite: 701 - 711 Identifikator: ISSN: 1615-4150
CoNE: https://pure.mpg.de/cone/journals/resource/958634688013