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Synlett 2009(1): 106-108  
DOI: 10.1055/s-0028-1087278
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Oxidative Desulfurization-Difluorination of Alkyl Aryl Thioethers: Synthesis of ω-Substituted 1,1-Difluoroalkanes

Verena Hugenberga,b, Günter Haufe*a,b
a Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstr. 40, 48149 Münster, Germany
b European Institute of Molecular Imaging (EIMI), Westfälische Wilhelms-Universität Münster, Mendelstr. 11, 48149 Münster, Germany
Fax: +49(251)8339772; e-Mail: haufe@uni-muenster.de;
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Publication History

Received 11 September 2008
Publication Date:
26 November 2008 (online)

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Abstract

An efficient new pathway towards ω-substituted gem-difluoroalkanes from corresponding aryl alkyl thioethers by oxidative desulfurization-difluorination with the reagents combination of 1,3-dibromo-5,5-dimethylhydantoin (DBH) as the oxidizer and pyridine-nonakis(hydrogen fluoride) as the fluoride source is described. Two succeeding fluoro-Pummerer-like rearrangements are suggested as a possible reaction mechanism.

Key words

desulfurization - fluorination - oxidation - synthesis - thioethers

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