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Issue 72, 2018
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Synthesis of heteroaromatic trifluoromethyl ethers with trifluoromethyl triflate as the source of the trifluoromethoxy group

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Abstract

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.

Graphical abstract: Synthesis of heteroaromatic trifluoromethyl ethers with trifluoromethyl triflate as the source of the trifluoromethoxy group

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Publication details

The article was received on 26 Jun 2018, accepted on 31 Jul 2018 and first published on 31 Jul 2018


Article type: Communication
DOI: 10.1039/C8CC05084H
Citation: Chem. Commun., 2018,54, 10124-10127
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    Synthesis of heteroaromatic trifluoromethyl ethers with trifluoromethyl triflate as the source of the trifluoromethoxy group

    Q. Zhang and J. F. Hartwig, Chem. Commun., 2018, 54, 10124
    DOI: 10.1039/C8CC05084H

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