title: Palladium-Catalyzed Synthesis of 3-Trifluoromethyl-Substituted 1,3-Butadienes by Means of Directed C-H Bond Functionalization.
abstract: A palladium-catalyzed C-H bond functionalization of acrylamides was developed to build up stereoselectively trifluoromethylated 1,3-butadienes. Using a tertiary amide as a directing group, olefins were selectively functionalized with 2-bromo-3,3,3-trifluoropropene to access these important fluorinated compounds. The methodology was extended to the construction of pentafluoroethyl-substituted 1,3-dienes. Mechanistic studies supported by density functional theory calculations suggested a redox neutral mechanism for this transformation.
authors.affiliation: Normandie Université, INSA Rouen , UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France.
authors.forename: Qun
authors.initials: Q
authors.lastname: Zhao
authors.affiliation: Normandie Université, INSA Rouen , UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France.
authors.forename: Vincent
authors.initials: V
authors.lastname: Tognetti
authors.affiliation: Normandie Université, INSA Rouen , UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France.
authors.forename: Laurent
authors.initials: L
authors.lastname: Joubert
authors.affiliation: Normandie Université, INSA Rouen , UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France.
authors.forename: Tatiana
authors.initials: T
authors.lastname: Besset
authors.affiliation: Normandie Université, INSA Rouen , UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France.
authors.forename: Xavier
authors.initials: X
authors.lastname: Pannecoucke
authors.affiliation: Normandie Université, INSA Rouen , UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France.
authors.forename: Jean-Philippe
authors.initials: JP
authors.lastname: Bouillon
authors.affiliation: Normandie Université, INSA Rouen , UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France.
authors.forename: Thomas
authors.identifier: 0000-0002-0503-9620
authors.initials: T
authors.lastname: Poisson