title: Stereospecific Synthesis of Tri- and Tetrasubstituted α-Fluoroacrylates by Mizoroki-Heck Reaction.
abstract: Ligand-free, efficient, palladium-catalyzed Mizoroki-Heck reaction between methyl α-fluoroacrylate and arene or hetarene iodides is reported for the first time. The reaction is stereospecific and provides fair to quantitative yields of fluoroalkenes. The Mizoroki-Heck reaction starting from more hindered and usually reluctant trisubstituted acrylate, to access tetrasubstituted fluoroalkenes, is also reported. Finally, the use of a three-step synthesis sequence, including Mizoroki-Heck reaction, allows the synthesis of fluorinated analogues of therapeutic agents with high yield.
authors.affiliation: Normandie Univ, COBRA, UMR 6014 & FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF, 1 rue Tesnière 76821 Mont-Saint-Aignan Cedex, France.
authors.forename: Kevin
authors.initials: K
authors.lastname: Rousée
authors.affiliation: Normandie Univ, COBRA, UMR 6014 & FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF, 1 rue Tesnière 76821 Mont-Saint-Aignan Cedex, France.
authors.forename: Jean-Philippe
authors.initials: JP
authors.lastname: Bouillon
authors.affiliation: Normandie Univ, COBRA, UMR 6014 & FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF, 1 rue Tesnière 76821 Mont-Saint-Aignan Cedex, France.
authors.forename: Samuel
authors.initials: S
authors.lastname: Couve-Bonnaire
authors.affiliation: Normandie Univ, COBRA, UMR 6014 & FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF, 1 rue Tesnière 76821 Mont-Saint-Aignan Cedex, France.
authors.forename: Xavier
authors.initials: X
authors.lastname: Pannecoucke
mesh_terms: D000179:Acrylates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000179:Acrylates; D006845:Hydrocarbons, Fluorinated; D006847:Hydrocarbons, Iodinated; D010165:Palladium