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Synthesis 2011(15): 2383-2386  
DOI: 10.1055/s-0030-1260074
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Fluorohydrins through Electrophilic Fluorination of Allyl Silanes

Weibo Wang, Bo Xu*, Gerald B. Hammond*
Department of Chemistry, University of Louisville, Louisville, KY 40292, USA
Fax: +1(502)8523899; e-Mail: bo.xu@louisville.edu; e-Mail: gb.hammond@louisville.edu;
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Publikationsverlauf

Received 29 April 2011
Publikationsdatum:
17. Juni 2011 (online)

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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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