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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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 Creators:
Lerch, Michael M.1, Author
Morandi, Bill1, 2, Author           
Wickens, Zachary K.1, Author
Grubbs, Robert H.1, Author
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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Free keywords: alkenes; ketones; palladium; regioselectivity; trifluoromethyl group
 Abstract: 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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Language(s): eng - English
 Dates: 2014-08-072014-08-11
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201404712
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem. Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH Verlag GmbH & Co. KGaA
Pages: - Volume / Issue: 53 (33) Sequence Number: - Start / End Page: 8654 - 8658 Identifier: ISSN: 1521-3773
CoNE: https://pure.mpg.de/cone/journals/resource/0570-0833