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Synthesis 2011(15): 2383-2386
DOI: 10.1055/s-0030-1260074
DOI: 10.1055/s-0030-1260074
SPECIALTOPIC
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Fluorohydrins through Electrophilic Fluorination of Allyl Silanes
Further Information
Received
29 April 2011
Publication Date:
17 June 2011 (online)
Publication History
Publication Date:
17 June 2011 (online)
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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