Synthesis of aromatic compounds containing a 1,1-dialkyl-2-trifluoromethyl group, a bioisostere of the tert-alkyl moiety

Bioorg Med Chem Lett. 2007 Nov 15;17(22):6079-85. doi: 10.1016/j.bmcl.2007.09.053. Epub 2007 Sep 18.

Abstract

1,1-Dialkyl-2-perfluoroalkyl compounds, which are potential metabolically stable bioisosteres of the tert-alkyl moiety, have been synthesized from the corresponding tertiary alcohols using titanium (IV) chloride-dimethylzinc or trimethylaluminium as the source of the methyl group. The synthetic methods proved to be versatile for synthesizing 1,1-dimethyl-2,2,2-trifluoroethyl compounds and analogs, including compounds containing aromatic and heterocyclic rings.

MeSH terms

  • Aluminum / chemistry
  • Hydrocarbons, Fluorinated / chemistry*
  • Molecular Structure
  • Organic Chemicals / chemical synthesis*
  • Organic Chemicals / chemistry
  • Organometallic Compounds / chemistry
  • Titanium / chemistry

Substances

  • Hydrocarbons, Fluorinated
  • Organic Chemicals
  • Organometallic Compounds
  • fluoromethane
  • dimethylzinc
  • titanium tetrachloride
  • Aluminum
  • Titanium