Synthesis of Heteroaromatic Trifluoromethyl Ethers with Trifluoromethyl Triflate as the Source of the Trifluoromethoxy Group

Synthesis of Heteroaromatic Trifluoromethyl Ethers with Trifluoromethyl Triflate as the Source of the Trifluoromethoxy Group

Chem. Comm. 201854, 10124-10127.

A series of nitrogen-heterocycles have been transformed to the corresponding trifluoromethyl or higher perfluoroalkyl ethers by reaction of the corresponding N-oxides with trifluoromethyl or higher perfluoroalkyl triflate. Trifluoromethyl triflate, which has generally been used as a precursor to [OCF3], is used here as a bifunctional reagent to render the heteroarene more electrophilic and to deliver the trifluoromethoxy group. This reagent was easily prepared on a large scale (>100 grams) and is stable in either pure form or as a stock solution. Applications and limitations of this method are reported.

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