Synthesis and characterization of novel trifluoromethyl-containing alcohols with Ruppert's reagent

Synthesis and characterization of novel new trifluoromethyl-containing alcohols using Ruppert's reagent [(trimethyl)trifluoromethylsilane] (1) are reported. The reactions of 1 with various ketones and aldehydes, such as tetraphenylcyclopentadienone (2a), 9,10-anthraquinone (2b), pyrenaldehyde (2c), 2,6-dimethyl-para-anisaldehyde (2d), and 2,3(methylenedioxy)benzaldehyde (2e) in the presence of a catalytic amount of tetrabutylammonium fluoride in THF led to the formation of the corresponding trifluoromethylated silyl ether derivatives 3a–e in almost quantitative yields. Acid hydrolysis of 3a–e gave the desired trifluoromethylated alcohol derivatives (4a–e) in excellent isolated yields. Compounds were characterized by IR, NMR (1H, 19F, 13C NMR), GCMS, and elemental analysis. Single crystal X-ray structures of 4a and 4b support the proposed products.

Utilization of Ruppert's reagent (TMS-CF3) enhances the formation of some novel trifluoromethylated alcohol derivatives from their corresponding ketone and aldehyde precursors.Figure optionsDownload as PowerPoint slideHighlights
► Ruppert's reagent in nucleophilic trifluoromethylation reactions of ketones and aldehydes.
► Direct synthesis of new trifluoromethylated alcohol derivatives from their corresponding ketones or aldehydes.
► X-ray crystallographic characterization of 1-trifluoromethyl-2,3,4,5-tetraphenylcyclo-pentadiene-1-ol and 9,10-bis(trifluoromethyl)-9.10-dihydroxyanthracene.