Abstract
In the presence of MS 4 Å in DMSO, trifluoromethylation of various aldehydes and ketones with trifluoromethyltrimethylsilane (TMSCF3) proceeded very smoothly to give the corresponding trifluoromethylated adduct in good to quantitative yields without a base catalyst.
Key words
trifluoromethylation - trifluoromethyltrimethylsilane - carbonyl compounds - DMSO
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Typical Procedure.
A solution of benzaldehyde (30 µL, 0.30 mmol) and TMSCF3 (54 µL, 0.36 mmol) in DMSO (2 mL) in the presence of powdered MS 4 Å (150 mg) was stirred at r.t. under an argon atmosphere. After 15 min, the reaction mixture was quenched with a phosphate buffer (pH 7, 20 mL). The organic materials were extracted with Et2O, dried over anhyd MgSO4, and the solvent was evaporated in vacuo. 1H NMR analysis (400 MHz) of the crude product using 1,1,2,2-tetrachloroethane as an internal standard shows that (2,2,2-trifluoro-1-phenylethoxy)trimethylsilane was obtained in quantitative yield. The product gave satisfactory 1H NMR, 13C NMR, 19F NMR, and IR spectra after the purification by TLC on silica gel.
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