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A New Electrophilic Trifluoromethylating Reagent
No.145(March 2012)
The design and synthesis of trifluoromethylated compounds have been studied, due to the unique feature of the trifluoromethylated compounds in pharmaceuticals, agrochemicals, and functional materials. Shibata et al. have developed a novel reagent 1 for the trifluoromethylation.1)
Typical procedure: the trifluoromethylation of 1-indanone-2-carboxylic acid methyl ester1)
To a stirred solution of 1-indanone-2-carboxylic acid methyl ester (20 mg, 0.105 mmol) in CH2Cl2 (0.5 mL) DBU (18.8 μL, 0.126 mmol) is added and stirred for 15 min at room temperature. The reagent 1 (51.4 mg, 0.158 mmol) is added and stirred for 15 min at room temperature. The solvent is evaporated, and the residue is purified by column chromatography on silica gel (benzene) to give the trifluoromethylated compound (25.1 mg, Y. 93%) as a pale yellow solid.
To a stirred solution of 1-indanone-2-carboxylic acid methyl ester (20 mg, 0.105 mmol) in CH2Cl2 (0.5 mL) DBU (18.8 μL, 0.126 mmol) is added and stirred for 15 min at room temperature. The reagent 1 (51.4 mg, 0.158 mmol) is added and stirred for 15 min at room temperature. The solvent is evaporated, and the residue is purified by column chromatography on silica gel (benzene) to give the trifluoromethylated compound (25.1 mg, Y. 93%) as a pale yellow solid.
References
- 1)Fluorinated Johnson reagent for tranfer-trifluoromethylation to carbon nucleophiles
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