Coordination Chemistry and Mechanisms of Metal-Catalyzed CC Coupling Reactions, Part 5. This work was supported by the Fonds der Chemischen Industrie and the Deutsche Forschungsgemeinschaft. Part 4: Ref.[7a].
Article first published online: 22 DEC 2003
Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
Angewandte Chemie International Edition in English
Volume 34, Issue 17, pages 1844–1848, September 15, 1995
How to Cite
Herrmann, W. A., Brossmer, C., Öfele, K., Reisinger, C.-P., Priermeier, T., Beller, M. and Fischer, H. (1995), Palladacycles as Structurally Defined Catalysts for the Heck Olefination of Chloro- and Bromoarenes. Angew. Chem. Int. Ed. Engl., 34: 1844–1848. doi: 10.1002/anie.199518441
Dedicated to Professor Henri Brunner on the occasion of his 60th birthday
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Received: 4 OCT 1994
- Heck olefination;
The catalytic CC coupling of chloroarenes by both the Heck and the Suzuki reactions has been achieved for the first time with new palladacycles of type 1, in which R can be, for instance, o-tolyl or mesityl. They are an order of magnitude more active than conventional catalysts and, moreover, thermally considerably more robust. But above all, the cleavage of the PC bond and the deposition of palladium is not observed. Analogous reactions with bromoarenes can also be catalyzed to advantage with 1. The Heck reaction of haloarenes with vinyl derivatives (e.g., n-butyl acryiate) gives (E)-styrene derivatives in one step. In the Suzuki reaction the haloarenes are converted into biphenyl derivatives with phenylbornic acid, also in one step.