Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis

J Am Chem Soc. 2015 May 6;137(17):5654-7. doi: 10.1021/jacs.5b02244. Epub 2015 Apr 27.

Abstract

The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F(•) transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Carboxylic Acids / chemistry*
  • Catalysis
  • Decarboxylation
  • Halogenation
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Photochemical Processes

Substances

  • Carboxylic Acids
  • Hydrocarbons, Fluorinated