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Vinyl Cation Stabilization by Silicon Enables a Formal Metal‐Free α‐Arylation of Alkyl Ketones
Authors:Amandine Pons  Jean Michalland  Wojciech Zawodny  Yong Chen  Veronica Tona  Nuno Maulide
Abstract:The ability of silicon to stabilize vinyl cationic species leads to a redox arylation of alkynes whereby the stringent limitations of reactivity and regioselectivity of alkyl‐substituted alkynes are lifted. This allows the synthesis of a range of α‐silyl‐α′‐arylketones under mild conditions in good to excellent yields and with high functional group tolerance, whereby the silicon moiety in the final products can either be removed for a formal acetone monoarylation transform, or capitalized upon for subsequent electrophilic substitutions at either side of the carbonyl group.
Keywords:α  -arylation  sigmatropic rearrangement  silicon β  -effect  vinyl cations
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