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Synthèses d'(arylsulfanyl)pyridines halogénées et leurs dérivés par couplages C-S et C-X catalysés par des complexes du palladium

Abstract : C–H activation of aryl compounds directed by 2-sulfonylpyridine and 2-sulfanylpyridine moiety for the formation of C–X (X = F, Cl, Br, I) bonds was studied. First, the syntheses of thioethers (2-(arylsulfanyl)pyridines) and sulfones (2-(arylsulfonyl)pyridines) were necessary for the progress of this project. A C–S coupling catalyzed by palladium complexe between thioaryls and halogenated heterocycles was performed for the synthesis of thioethers. The cheap ligand bis(diphenylphosphino)ferrocene (dppf) was used for this convenient reaction. Then, oxidation of thioethers was performed to synthesize sulfones. Halogenation of these compounds was studied with ortho-directed C–H activation catalyzed with palladium. Different catalytic systems were elaborated allowing the formations of C–Br, C–I, C–Cl and C–F bonds. These couplings are selective in ortho position of directing group and one or both positions can be functionalized.
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https://tel.archives-ouvertes.fr/tel-02067489
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Submitted on : Thursday, March 14, 2019 - 11:44:07 AM
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  • HAL Id : tel-02067489, version 1

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Johan Guilbaud. Synthèses d'(arylsulfanyl)pyridines halogénées et leurs dérivés par couplages C-S et C-X catalysés par des complexes du palladium. Catalyse. Université Bourgogne Franche-Comté, 2018. Français. ⟨NNT : 2018UBFCK047⟩. ⟨tel-02067489⟩

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