Trifluoromethylation of Aliphatic Halogen Compounds

Bouillon, JP.;Maliverney, C.;Merenyi, R.;Viehe, HG.
(1991) Royal Society of Chemistry. Journal: Perkin Transactions 1 — n° 9, p. 2147-2149 (1991)

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  • Bouillon, JP.
    Author
  • Maliverney, C.
    Author
  • Merenyi, R.
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  • Viehe, HG.
    Author
Abstract
Aryl, heteroaryl or vinyl halides can be trifluoromethylated using CF3CO2Na-Cul. With alkyl iodides, however, the method fails, yielding trifluoroacetyl esters instead. Allylic halogens can be substituted with Burton's reagent, obtained from dihalogenodifluoromethane via CF3CdHal and transmetallation with Cul. A new access to trifluoropropionic acid is thereby found. Prop-2-ynyl bromide produces trifluoromethylallene. Attempts at trifluoromethylation of bromoacetate with CF3CO2Na-Cul in NMP (N-methyl-2-pyrrolidone) solution led to formation of the trifluoroacetoxy derivative and of a formal adduct of hexafluoroacetone to the alpha-position of NMP.
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Bouillon, JP., Maliverney, C., Merenyi, R., & Viehe, HG. (1991). Trifluoromethylation of Aliphatic Halogen Compounds. Royal Society of Chemistry. Journal: Perkin Transactions 1, 9, 2147-2149. https://doi.org/10.1039/p19910002147 (Original work published 1991)