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Synlett 2012; 23(7): 1064-1068
DOI: 10.1055/s-0031-1290757
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© Georg Thieme Verlag Stuttgart · New York

Meerwein’s Reagent Mediated, Significantly Enhanced Nucleophilic Fluorination on Alkoxysilanes

Yogesh R. Jorapur
a   Department of Chemical Engineering, Nara National College of Technology, 22 Yata-cho Yamatokoriyama, Nara, 639-1080, Japan
b   Core Research for Evolutional Science and Technology (CREST), JST Agency, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan, Fax: +81(743)556154   Email: shimada@chem.nara-k.ac.jp
,
Toyoshi Shimada*
a   Department of Chemical Engineering, Nara National College of Technology, 22 Yata-cho Yamatokoriyama, Nara, 639-1080, Japan
b   Core Research for Evolutional Science and Technology (CREST), JST Agency, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan, Fax: +81(743)556154   Email: shimada@chem.nara-k.ac.jp
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Publication History

Received: 24 January 2012

Accepted after revision: 14 February 2012

Publication Date:
05 April 2012 (online)

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Abstract

We developed a new facile method to fluorosilanes from alkoxysilanes using Meerwein’s reagent. Our protocol afforded fluo­rosilanes in excellent yields in various organic solvents including acetonitrile under mild reaction conditions at room temperature. We also proposed a reaction mechanism with the probable silyloxonium intermediates.

Key words

Meerwein’s reagent - nucleophilic fluorination - silyl­oxonium - fluorine - silicon

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    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
  • Supporting Information
 

  • References and Notes

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