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

MPG-Autoren
http://pubman.mpdl.mpg.de/cone/persons/resource/persons145542

Morandi,  Bill
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA);
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Zitation

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.


Zitierlink: http://hdl.handle.net/11858/00-001M-0000-0025-BA99-5
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.