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Ligand Free Palladium‐Catalyzed Synthesis of α‐Trifluoromethylacrylic Acids and Related Acrylates by Three‐Component Reaction

Abstract : Aryl iodides and 2‐(trifluoromethyl)acrylic acid reacted together in ligand‐free Mizoroki‐Heck reaction furnishing a quick and efficient access to highly valuable α‐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 α‐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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https://hal-normandie-univ.archives-ouvertes.fr/hal-02466844
Contributor : Madeleine Roux-Merlin <>
Submitted on : Tuesday, February 4, 2020 - 4:24:41 PM
Last modification on : Thursday, July 2, 2020 - 3:29:21 AM

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Pan Xiao, Xavier Pannecoucke, J.-P. Bouillon, Samuel Couve-Bonnaire. Ligand Free Palladium‐Catalyzed Synthesis of α‐Trifluoromethylacrylic Acids and Related Acrylates by Three‐Component Reaction. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2020, 362 (4), pp.949-954. ⟨10.1002/adsc.201901446⟩. ⟨hal-02466844⟩

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