Palladium-Catalyzed Synthesis of 3-Trifluoromethyl-Substituted 1,3-Butadienes by Means of Directed C-H Bond Functionalization - Archive ouverte HAL Access content directly
Journal Articles Organic Letters Year : 2017

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

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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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hal-02046319 , version 1 (22-02-2019)

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