Palladium-Catalyzed Synthesis of 3-Trifluoromethyl-Substituted 1,3-Butadienes by Means of Directed C-H Bond Functionalization

Qun Zhao (1) , Vincent Tognetti (1) , Laurent Joubert (1) , Tatiana Besset (1) , Xavier Pannecoucke (1) , J.-P. Bouillon (1) , Thomas Poisson (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

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.

Domaines: Chimie

Qun Zhao, Vincent Tognetti, Laurent Joubert, Tatiana Besset, Xavier Pannecoucke, et al.. Palladium-Catalyzed Synthesis of 3-Trifluoromethyl-Substituted 1,3-Butadienes by Means of Directed C-H Bond Functionalization. Organic Letters, 2017, 19 (8), pp.2106-2109. ⟨10.1021/acs.orglett.7b00704⟩. ⟨hal-02046319⟩