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. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 8654-8658 |
| Number of pages | 5 |
| Journal | Angewandte Chemie International Edition |
| Volume | 53 |
| Issue number | 33 |
| DOIs | |
| State | Published - Jul 18 2014 |
| Externally published | Yes |
Bibliographical note
KAUST Repository Item: Exported on 2020-10-01Acknowledgements: 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.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.