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.
Palladium-Catalyzed Substitution of Allylic Fluorides†
Article first published online: 13 JAN 2009
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 48, Issue 7, pages 1296–1299, February 2, 2009
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
- Issue published online: 28 JAN 2009
- Article first published online: 13 JAN 2009
- Manuscript Revised: 12 NOV 2008
- Manuscript Received: 1 SEP 2008
- allyl ligands;
- homogeneous catalysis;
- reaction mechanisms
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.