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Transition-Metal-Free α-Vinylation of Enolizable Ketones with β-Bromostyrenes

Abstract : An α-vinylation of enolizable ketones has been developed by using β-bromostyrenes and a KOtBu/NMP system. β,γ-Unsaturated ketones of E configuration were obtained in excellent yield and selectivity. Further synthetic possibilities are highlighted by one-pot functionalization via trapping of intermediate dienolates with alkyl, allyl, benzyl, and propargyl halides to generate quaternary centers. The reported transformation is believed to involve phenylacetylene and propargylic alcohol derivatives.
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https://hal.umontpellier.fr/hal-02098027
Contributor : Odile Hennaut <>
Submitted on : Thursday, January 7, 2021 - 11:25:38 AM
Last modification on : Tuesday, February 9, 2021 - 11:24:48 AM

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Yassir Zaid, Cleve Dionel Mboyi, Martin Pichette Drapeau, Léa Radal, Fouad Ouazzani Chahdi, et al.. Transition-Metal-Free α-Vinylation of Enolizable Ketones with β-Bromostyrenes. Organic Letters, American Chemical Society, 2019, 21 (6), pp.1564-1568. ⟨10.1021/acs.orglett.8b04004⟩. ⟨hal-02098027⟩

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