Synthesis of Difluorinated Enynes through Sonogashira-Type Coupling

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...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 21; pp. 5688 - 5691
Main Authors Fujino, Takumi, Hinoue, Tomoaki, Usuki, Yoshinosuke, Satoh, Tetsuya
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.11.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACTIVATION
HETEROARENES
ANALOGS
ACIDS
H BOND FUNCTIONALIZATIONS
ARYLATION
TERMINAL ALKYNES
ARYL
DIFLUOROVINYLATION
TOSYLATES
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Summary: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.
Bibliography:KAKEN
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b02919