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Fluorination of sulfanyl amides using difluoroiodoarene reagents

Motherwell, WB; Greaney, MF; Edmunds, JJ; Steed, JW; (2002) Fluorination of sulfanyl amides using difluoroiodoarene reagents. J CHEM SOC PERK T 1 (24) 2816 - 2826. 10.1039/b209078c.

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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 alpha-position to sulfur undergo fluorination in DCM with cleavage of the carbon-sulfur bond to form novel fluorinated beta-lactams 4. Sulfides with electron-withdrawing groups in the alpha-position undergo alpha-fluorination in a process analogous to the classical Pummerer reaction. This Fluoro-Pummerer reaction has been exemplified for a range of simple alpha-phenylsulfanylacetamides 14-19. When beta-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 alpha,beta-difluoro sulfides 45-47.

Type:Article
Title:Fluorination of sulfanyl amides using difluoroiodoarene reagents
DOI:10.1039/b209078c
Keywords:ELECTROLYTIC PARTIAL FLUORINATION, IODOTOLUENE DIFLUORIDE, ORGANIC-COMPOUNDS, LACTAMS, MONOFLUORINATION, SULPHOXIDES, REACTIVITY
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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