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  Rapid Access to β-Trifluoromethyl-Substituted Ketones: Harnessing Inductive Effects in Wacker-Type Oxidations of Internal Alkenes

Lerch, M. M., Morandi, B., Wickens, Z. K., & Grubbs, R. H. (2014). Rapid Access to β-Trifluoromethyl-Substituted Ketones: Harnessing Inductive Effects in Wacker-Type Oxidations of Internal Alkenes. Angewandte Chemie International Edition, 53(33), 8654-8658. doi:10.1002/anie.201404712.

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 Urheber:
Lerch, Michael M.1, Autor
Morandi, Bill1, 2, Autor           
Wickens, Zachary K.1, Autor
Grubbs, Robert H.1, Autor
Affiliations:
1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA), ou_persistent22              
2Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2040309              

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Schlagwörter: alkenes; ketones; palladium; regioselectivity; trifluoromethyl group
 Zusammenfassung: We present a practical trifluoromethyl-directed Wacker-type oxidation of internal alkenes that enables rapid access to β-trifluoromethyl-substituted ketones. Allylic trifluoromethyl-substituted alkenes bearing a wide range of functional groups can be oxidized in high yield and regioselectivity. The distance dependence of the regioselectivity was established by systematic variation of the number of methylene units between the double bond and the trifluoromethyl group. The regioselectivity enforced by traditional directing groups could even be reversed by introduction of a competing trifluoromethyl group. Besides being a new powerful synthetic method to prepare fluorinated molecules, this work directly probes the role of inductive effects on nucleopalladation events.

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Sprache(n): eng - English
 Datum: 2014-08-072014-08-11
 Publikationsstatus: Erschienen
 Seiten: -
 Ort, Verlag, Ausgabe: -
 Inhaltsverzeichnis: -
 Art der Begutachtung: Expertenbegutachtung
 Identifikatoren: DOI: 10.1002/anie.201404712
 Art des Abschluß: -

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Titel: Angewandte Chemie International Edition
  Kurztitel : Angew. Chem. Int. Ed.
Genre der Quelle: Zeitschrift
 Urheber:
Affiliations:
Ort, Verlag, Ausgabe: Weinheim : Wiley-VCH Verlag GmbH & Co. KGaA
Seiten: - Band / Heft: 53 (33) Artikelnummer: - Start- / Endseite: 8654 - 8658 Identifikator: ISSN: 1521-3773
CoNE: https://pure.mpg.de/cone/journals/resource/0570-0833