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Issue 24, 2002
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Fluorination of sulfanyl amides using difluoroiodoarene reagents

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Abstract

A range of sulfur-containing amides have been fluorinated with the hypervalent iodine difluoride reagents 1, and two principal reaction pathways identified. Cephalosporin esters 2 having a heteroatom in the α-position to sulfur undergo fluorination in DCM with cleavage of the carbon–sulfur bond to form novel fluorinated β-lactams 4. Sulfides with electron-withdrawing groups in the α-position undergo α-fluorination in a process analogous to the classical Pummerer reaction. This Fluoro-Pummerer reaction has been exemplified for a range of simple α-phenylsulfanylacetamides 14–19. When β-hydrogens are present in the substrate a different route is followed, with deprotonation by basic fluoride taking place to yield vinyl sulfides 41–43. When an excess of the fluorinating reagent is used these vinyl sulfides can undergo further reaction in a novel tandem Pummerer-Additive-Pummerer process to yield α,β-difluoro sulfides 45–47.

Graphical abstract: Fluorination of sulfanyl amides using difluoroiodoarene reagents

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Publication details

The article was received on 18 Sep 2002, accepted on 06 Nov 2002 and first published on 22 Nov 2002


Article type: Paper
DOI: 10.1039/B209078C
Citation: J. Chem. Soc., Perkin Trans. 1, 2002, 2816-2826
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    Fluorination of sulfanyl amides using difluoroiodoarene reagents

    W. B. Motherwell, M. F. Greaney, J. J. Edmunds and J. W. Steed, J. Chem. Soc., Perkin Trans. 1, 2002, 2816
    DOI: 10.1039/B209078C

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