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Full Paper
Pd-EnCatTM TPP30 as a Catalyst for the Generation of Highly Functionalized Aryl- and Alkenyl-Substituted Acetylenes via Microwave-Assisted Sonogashira Type Reactions
Article first published online: 24 JUL 2009
DOI: 10.1002/ejoc.200900344
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Sedelmeier, J., Ley, S. V., Lange, H. and Baxendale, I. R. (2009), Pd-EnCatTM TPP30 as a Catalyst for the Generation of Highly Functionalized Aryl- and Alkenyl-Substituted Acetylenes via Microwave-Assisted Sonogashira Type Reactions. European Journal of Organic Chemistry, 2009: 4412–4420. doi: 10.1002/ejoc.200900344
Publication History
- Issue published online: 24 AUG 2009
- Article first published online: 24 JUL 2009
- Manuscript Received: 30 MAR 2009
Funded by
- German Academic Exchange Service (DAAD)
- Alexander von Humboldt Foundation
- Engineering and Physical Sciences Research Council (EPSRC)
Keywords:
- Cross-coupling;
- Heterogeneous catalysis;
- Reusable catalyst;
- Palladium;
- Microwave chemistry;
- Enynes
Graphical Abstract
Without using any copper species and under robust conditions, rapid microwave-assisted Sonogashira cross-coupling of aryl iodides and bromides with terminal alkynes using Pd-EnCatTM TPP30 were conducted. Both electron-rich and electron-deficient aryl halides reacted smoothly with a broad variety of terminal alkynes in MeCN at 100–120 °C.
Abstract
We report a rapid microwave-assisted Sonogashira cross-coupling of aryl iodides and bromides with terminal alkynes using Pd-EnCatTM TPP30. Both electron-rich and electron-deficient aryl halides reacted smoothly with a broad variety of terminal alkynes in MeCN at 100–120 °C. The coupling products were obtained in good to excellent yields and in high purity. This reaction can be performed under copper- and DMF-free conditions and does not require an inert atmosphere. Furthermore, the encapsulated catalyst can be recovered and recycled by a simple filtration of the reaction mixture. It can be reused in further reactions with only minor decrease in activity. Additionally, we were able to produce a variety of enyne derivatives under modified conditions employing the same Pd-EnCatTM source. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)