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Synthesis of Difluorinated Enynes through Sonogashira-Type Coupling
Takumi Fujino1, Tomoaki Hinoue1, Yoshinosuke Usuki1
1Department of Chemistry, Graduate School of Science, Osaka City University , 3-3-138 Sugimoto, Sumiyoshi-ku, Osaka 558-8585, Japan.
Abstract:
The Sonogashira-type coupling of 2,2-difluoroethenyl tosylate with a variety of aliphatic and aromatic terminal alkynes proceeds smoothly even at room temperature to produce the corresponding difluorinated enyne derivatives. 2,2-Difluoroethenyl tosylate is a useful difluoroethenyl source because of its ready availability from 2,2,2-trifluoroethanol. Some of the obtained enynes exhibit strong fluorescence in the solid state. Further derivatization of a difluorinated enyne through Rh(III)-catalyzed oxidative coupling has also been examined.
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