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Electrophilic Trifluoromethylating Reagent

1-Trifluoromethyl-3,3-dimethyl-1,2-benziodoxole (1) is a hypervalent iodine compound used for electrophilic trifluoromethylation developed by Togni and co-workers. 1 reacts with β-keto esters and α-nitro esters to introduce a trifluoromethyl group on their α-carbons. 1 also reacts with thiols and primary- and secondary phosphines to generate trifluoromethyl sulfides and trifluoromethyl substituted phosphines respectively. 1 is a useful trifluoromethylating reagent which can be applicable to various substrates.
Typical Procedure: 1a)
To a vigorously stirred suspension of Ethyl 1-oxoindane-2-carboxylate (0.041 g, 0.2 mmol), K2CO3 (0.083 g, 0.6 mmol, 3.0 eq.), and n-Bu4NI (0.0074 g, 0.02 mmol, 10 mol%) in MeCN (2 mL), solid 1 (0.099 g, 0.3 mmol, 1.5 eq.) was added at ambient temperature. After the mixture had been stirred for 28 h, saturated aqueous NaHCO3 was added. Extraction of the aqueous phase three times with EtOAc, drying with MgSO4 filtration, and evaporation of the solvent under reduced pressure yielded a brownish oil. After purification by chromatography (silica gel 60; eluent: hexanes/EtOAc (25:1)) Ethyl 1-oxo-2-trifluoromethylindane-2-carboxylate (0.036 g, 0.135 mmol, Y. 67%) was obtained as a colorless oil.


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