Synthesis of aromatic compounds containing a 1,1-dialkyl-2-trifluoromethyl group, a bioisostere of the tert-alkyl moiety.
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.
Tanaka
Hirotaka
H
Pfizer Global Research & Development, Nagoya Laboratories, 5-2 Taketoyo, Aichi, Japan.
Shishido
Yuji
Y
D000535:Aluminum / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D015394:Molecular Structure; D009930:Organic Chemicals / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D014025:Titanium / Q000737:chemistry
D006845:Hydrocarbons, Fluorinated; D009930:Organic Chemicals; D009942:Organometallic Compounds; C029999:fluoromethane; C511262:dimethylzinc; C025096:titanium tetrachloride; D000535:Aluminum; D014025:Titanium