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

Author:
Zhang, Qing-Wei, Hartwig, John F.
Source:
Chemical communications 2018 v.54 no.72 pp. 10124-10127
ISSN:
1364-548X
Subject:
Lewis acids, chemical reactions, ethers, heterocyclic compounds, perfluorocarbons
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.
Agid:
6166340