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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