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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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046319
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:40:33 PM
Last modification on : Monday, July 27, 2020 - 3:15:58 PM

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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, American Chemical Society, 2017, 19 (8), pp.2106-2109. ⟨10.1021/acs.orglett.7b00704⟩. ⟨hal-02046319⟩

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