.ALPHA.-Fluorination of sulfides with N-fluoropyridinium triflates.
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The reaction of sulfides possessing α-hydrogen with various <I>N</I>-fluoropyridinium salts was examined. While the fluorinating power increased in the order of <I>N</I>-fluoro-2,4,6-trimethylpyridinium triflate <B>1</B><<I>N</I>-fluoropyridinium triflate <B>2</B><<I>N</I>-fluoro-3,5-dichloropyridinium triflate <B>3</B>, the yield of an α-fluoro sulfide decreased in the order of <B>1</B>><B>2</B>, and <B>3</B> no longer produced the α-fluoro sulfide. Triflate <B>1</B> was more reactive than the corresponding tetrafluoroborate <B>4</B>. Thus, it was shown that <B>1</B> satisfactorily fluorinated various kinds of sulfides under very mild conditions, giving α-fluoro sulfides. A two-step mechanism, oxidative fluorination of sulfur and Pummerer-type rearrangement, was proposed for the fluorination. The corresponding α-fluoro sulfoxide or sulfones were easily prepared from the sulfides by successive fluorination–oxidation procedure.
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