(E)-Trimethyl(perfluoroprop-1-enyl)silane As a Reagent to Transfer Perfluoroprop-1-enyl Group to Ketones and Aldehydes Catalyzed by Fluoride

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Abstract

Analogous to trifluoromethyltrimethylsilane (Ruppert's reagent) (E)-trimethyl(perfluoroprop-1-enyl)silane (1), prepared by deprotonation of (Z)-1,2,3,3,3-pentafluoroprop-1-ene (2a) at −78 °C in the presence of chlorotrimethylsilane, was shown to transfer the perfluoroprop-1-enyl group to a number of electrophiles containing carbonyl group in the presence of catalytic amount of fluoride anion. The perfluoroprop-1-enyl group was transferred to formaldehyde, acetaldehyde, benzaldehyde, acetone, trifluoroacetophenone resulting in formation of corresponding TMS-ethers of secondary and tertiary alcohols containing Z-CF3CF═CF– fragment. With some substrates such as hexafluoroacetone, formaldehyde, and trifluoroacetophenone, substituted 5-membered dioxolane products of the reaction can be obtained, depending on the reaction conditions and the source of fluoride catalyst.

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