Abstract
A truly catalytic nucleophilic trifluoromethylation reaction of carbonyl compounds with Ruppert’s reagent, Me3 SiCF3 , has been shown to be efficiently promoted by a P(t -Bu)3 -DMF system. Imines were also converted to the desired α-trifluoromethyl amines under similar reaction conditions.
Key words
trifluoromethylation - fluorine - aldehydes - imines - Lewis bases
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Typical Experimental Procedure.
tert -butylphosphine [P(t -Bu)3 , 3.9 mg, 0.019 mmol]) was placed in a round-bottomed flask under N2 . Dry DMF (0.25 mL) and 2-naphthaldehyde (1b , 30 mg, 0.19 mmol) were added. To the stirred solution, Me3 SiCF3 (57 µL, 0.38 mmol) was added at r.t. The mixture was stirred at r.t. for 0.5 h; the reaction was concentrated under reduced pressure. The residue was chromatographed on silica gel using hexane to afford 2b in 99% yield.
