Enantioselective alpha-trifluoromethylation of aldehydes via photoredox organocatalysis

J Am Chem Soc. 2009 Aug 12;131(31):10875-7. doi: 10.1021/ja9053338.


The first enantioselective, organocatalytic alpha-trifluoromethylation and alpha-perfluoroalkylation of aldehydes have been accomplished using a readily available iridium photocatalyst and a chiral imidazolidinone catalyst. A range of alpha-trifluoromethyl and alpha-perfluoroalkyl aldehydes were obtained from commercially available perfluoroalkyl halides with high efficiency and enantioselectivity. The resulting alpha-trifluoromethyl aldehydes were subsequently shown to be versatile precursors for the construction of a variety of enantioenriched trifluoromethylated building blocks.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Chlorofluorocarbons, Methane / chemistry*
  • Methylation
  • Oxidation-Reduction
  • Photochemical Processes*
  • Stereoisomerism


  • Aldehydes
  • Chlorofluorocarbons, Methane
  • fluoroform