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We thank Prof. Guy Lloyd-Jones (Bristol) for free exchange of information, and Johnson–Matthey for the loan of palladium salts. We thank a referee for comments that stimulated further experiments. Dr. Sophie Purser helped in the initial phases of the work. Support from the CRL Spectroscopy Facilities (Dr. T. D. W. Claridge) is gratefully acknowledged.
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Communication
Palladium-Catalyzed Substitution of Allylic Fluorides†
Article first published online: 13 JAN 2009
DOI: 10.1002/anie.200804310
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Hazari, A., Gouverneur, V. and Brown, John M. (2009), Palladium-Catalyzed Substitution of Allylic Fluorides. Angew. Chem. Int. Ed., 48: 1296–1299. doi: 10.1002/anie.200804310
- †
Publication History
- Issue published online: 28 JAN 2009
- Article first published online: 13 JAN 2009
- Manuscript Revised: 12 NOV 2008
- Manuscript Received: 1 SEP 2008
Keywords:
- allyl ligands;
- allylation;
- homogeneous catalysis;
- palladium;
- reaction mechanisms
Abstract
As unusual substrates for the Tsuji–Trost allylation reaction, allylic fluorides are responsive to palladium-catalyzed substitution. Their activity towards this reaction fits in the series OCO2Me>OBz≫F≫OAc. The classic stereoretention mechanism that involves sequential inversions does not operate in this case. Several distinct cases are considered.