Synthesis of Fluorohydrins through Electrophilic Fluorination of Allyl Silanes

Abstract

A convenient method for the efficient and regioselective monofluorination of allyl silanes to afford 1-fluoro-3-silyl-2-ols in 43-62% yields via fluorohydroxylation, using Selectfluor as the eletrophilic fluorination reagent has been developed. The regioselectivity can be rationalized by considering the stabilization of the β-carbocation intermediate by the silyl group.

Key words

allyl silanes - fluorination - fluorohydrins - regioselectivity

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