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Synfacts 2006(8): 0773-0773
DOI: 10.1055/s-2006-941981
DOI: 10.1055/s-2006-941981
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Fluorinated Pyrones
Y. Wang, D. J. Burton*
University of Iowa, Iowa City, USA
Further Information
Publication History
Publication Date:
21 July 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200608/lookinside/thumbnails/10.1055-s-2006-941981-1.jpg)
Significance
A one-pot Sonogashira coupling-lactonization of cis-2,3-difluoro-3-iodo acrylic acid with terminal alkynes to give 3,4-difluoro-6-substituted-2-pyrones is reported. Aliphatic, heterocyclic and aromatic alkynes participate in this reaction to give pyrones in modest to good yields. Although electron-withdrawing and -donating groups on the aromatic acetylenes showed little effect on yields (e.g., CF3, 69%; OMe, 71%), the yield of the pyridyl (43%) was compromised. An X-ray crystallographic structural analysis of the trifluorophenyl derivative was determined. A mechanism containing two catalytic cycles was proposed for the transformation.