DOI

The reactions of 1-aryl-3-bromo-2,2-difluoropropan-1-ones [Ar(CO)CF2CH2Br] with various arenes Ar′H in the superacid TfOH at room temperature for 1–7 h result in the formation of products of hydroarylation of the carbonyl group, 1,1-diaryl-3-bromo-2,2-difluoropropan-1-ols [ArAr′C(OH)CF2CH2Br], in yields up to 85 %. The reaction with benzene goes deeper and leads to 1-aryl-3-bromo-2,2-difluoro-1,1-diphenylpropanes [ArCPh2CF2CH2Br] in good yields. Mainly, the bromomethyl group (CH2Br) of starting ketones remains untouched under the superacidic conditions. Cationic intermediates of the reaction have been studied by means of NMR spectroscopy. Plausible reaction mechanism is discussed.

Original languageEnglish
Pages (from-to)5905-5911
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number34
Early online date13 Aug 2019
DOIs
StatePublished - 15 Sep 2019

    Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

    Research areas

  • Aromatic substitution, Difluoroalcohols, Difluoroketones, Protonation, Triflic acid

ID: 49830567