eFluorination using cheap and readily available tetrafluoroborate salts

Authors

  • Kevin Lam University of Greenwich ,
  • Matthew Leech University of Greenwich ,
  • Dmitrii Nagornii University of Greenwich ,
  • Jamie Walsh University of Greenwich ,
  • Cyrille Kiaku University of Greenwich ,
  • Darren Poole Discovery High-Throughput Chemistry, Medicinal Chemistry, GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY, UK ,
  • Joseph Mason Discovery High-Throughput Chemistry, Medicinal Chemistry, GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY, UK ,
  • Iain Goodall University of Greenwich ,
  • Perry Devo University of Greenwich

Abstract

A new practical electrochemical method for the rapid, safe, and mild synthesis of tertiary hindered alkyl fluorides from easily accessed carboxylic acids has been developed without the need for hydrofluoric acid derivatives or non-glass reactors. In this anodic fluorination, collidinium tetrafluoroborate (Coll·HBF4) is advantageous as a supporting electrolyte and fluoride donor. A wide range of functional groups has been shown to be compatible with this new methodology. The possibility of scale-up using flow electrochemistry has also been demonstrated, thus representing a viable procedure for tertiary fluorination on a larger scale.

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Supplementary material

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Supporting information