The electrophilic fluorination of enol esters using SelectFluor: a polar two-electron process

Susanna H. Wood, Stephen Etridge, Alan R. Kennedy, Jonathan M. Percy, David J. Nelson

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Abstract

The reaction of enol esters with SelectFluor is facile and leads to the corresponding α-fluoroketones under mild conditions and, as a result, this route is commonly employed for the synthesis of medicinally important compounds such as fluorinated steroids. However, despite the use of this methodology in synthesis, the mechanism of this reaction and the influence of structure on reactivity are unclear. We present a rigorous mechanistic study of the fluorination of these substrates, informed primarily by detailed and robust kinetic experiments. The results of this study implicate a polar two-electron process via an oxygen-stabilised carbenium species, rather than a single-electron process involving radical intermediates. The structure/reactivity relationships revealed here will assist synthetic chemists in deploying this type of methodology in the syntheses of α-fluoroketones
Original languageEnglish
Pages (from-to)5574-5585
Number of pages12
JournalChemistry - A European Journal
Volume25
Issue number21
Early online date6 Feb 2019
DOIs
Publication statusPublished - 11 Apr 2019

Keywords

  • SelectFluor
  • electrophilic fluorination
  • enol esters
  • kinetic experiments
  • oxygen-stabilised carbenium species

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