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Sequential Deconjugative Electrophilic Fluorination/Cross-Metathesis: Toward the Synthesis of Fluoro Analogues of Biologically Active Compounds

Abstract : For the first time, a deconjugative electrophilic fluorodesilylation reaction was accomplished. γ-Silyl butenamides were treated with Selectfluor to provide α-fluoro-β,γ-unsaturated amides. Other sources of electrophilic fluorine were not efficient or gave protodesilylated side products. The electrophilic fluorodesilylation reaction was followed by a ruthenium-catalyzed cross-metathesis of the resulting functionalized allylic fluoride. The fluorodesilylation/cross-metathesis sequence is ideal for the synthesis of fluoro analogues of symbior­amide.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046140
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:31:57 PM
Last modification on : Thursday, July 2, 2020 - 3:29:49 AM

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Matthieu Bédier, Samir Bouzbouz. Sequential Deconjugative Electrophilic Fluorination/Cross-Metathesis: Toward the Synthesis of Fluoro Analogues of Biologically Active Compounds. SYNLETT, Georg Thieme Verlag, 2015, 26 (18), pp.2531-2536. ⟨10.1055/s-0035-1560318⟩. ⟨hal-02046140⟩

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