Pd-EnCat (TM) TPP30 as a Catalyst for the Generation of Highly Functionalized Aryl- and Alkenyl-Substituted Acetylenes via Microwave-Assisted Sonogashira Type Reactions

Sedelmeier, Joerg; Ley, Steven V.; Lange, Heiko; Baxendale, Ian R.

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)

Citation

Sedelmeier, J., Ley, S. V., Lange, H., & Baxendale, I. R. (2009). Pd-EnCat (TM) 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, 4412-4420. https://doi.org/10.1002/ejoc.200900344

• Journal Article Type: Article
• Acceptance Date: Jul 24, 2009
• Online Publication Date: Aug 24, 2009
• Publication Date: 2009-09
• Deposit Date: Jul 14, 2014
• Journal: European Journal of Organic Chemistry
• Print ISSN: 1434-193X
• Electronic ISSN: 1099-0690
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Issue: 26
• Pages: 4412-4420
• DOI: https://doi.org/10.1002/ejoc.200900344
• Public URL: https://durham-repository.worktribe.com/output/1447893