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Ligand Free Palladium‐Catalyzed Synthesis of α‐Trifluoromethylacrylic Acids and Related Acrylates by Three‐Component Reaction
Author(s) -
Xiao Pan,
Pannecoucke Xavier,
Bouillon JeanPhilippe,
CouveBonnaire Samuel
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901446
Subject(s) - chemistry , catalysis , aryl , ligand (biochemistry) , palladium , trifluoromethyl , substituent , carboxylate , combinatorial chemistry , salt (chemistry) , catalytic cycle , acrylic acid , organic chemistry , polymer , copolymer , biochemistry , alkyl , receptor
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‐CF 3 ‐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.