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Published August 11, 2014 | public
Journal Article

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


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.

Additional Information

© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Early View (Online Version of Record published before inclusion in an issue). Received: April 25, 2014. Article first published online: 18 Jul 2014. We gratefully acknowledge financial support from the King Abdullah University of Science and Technology Centre in Development, King Fahd University of Petroleum and Minerals, and the NSF. Furthermore, we thank the Gordon and Betty Moore Foundation, the SNSF for a fellowship to B.M., and the Swiss Study Foundation for a fellowship to M.M.L.

Additional details

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