Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 4, Pages 949-954Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901446
Keywords
Fluoroalkenes; trifluoromethyl; acrylates; palladium; silver
Categories
Funding
- INSA Rouen
- Rouen University
- CNRS
- EFRD
- Labex SynOrg [ANR-11-LABX-0029]
- Region Haute-Normandie (Crunch Network)
- CSC (China Scholarship Council)
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Aryl iodides and 2-(trifluoromethyl)acrylic acid reacted together in ligand-free Mizoroki-Heck reaction furnishing a quick and efficient access to highly valuable alpha-trifluoromethylacrylic acids. The useful transformation was independent with regard to the electronic nature of the aryl group substituent. A three-component one-pot version was also developed to give diverse substituted acrylates. The versatility of alpha-trifluoromethylacrylic acids was demonstrated by quick access to 3-CF3-coumarins as well as fluorinated analogues of therapeutic or cosmetic agents. Finally, we proposed a catalytic cycle based on the silver carboxylate salt, identified as a key intermediate in the reaction.
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