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New Umemoto’s Reagent II for Trifluoromethylation

No.172(January 2017)
D5335
2,8-Difluoro-5-(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium Trifluoromethanesulfonate (1)
The trifluoromethyl group has unique properties such as high electronegativity, metabolic stability and lipophilicity. The installment of a trifluoromethyl group is one of the significant functionalizations and is utilized for development in various fields, like pharmaceuticals, agricultural chemicals and material science. S-(Perfluoroalkyl)dibenzothiophenium salt 1, which has been developed by Umemoto et al., is useful as an electrophilic trifluoromethylating reagent. 1 is applicable for many reactions under basic conditions such as trifluoromethylation of β-ketoesters at the α-position, direct trifluoromethylation of indoles at the 2-position, and hydroxytrifluoromethylation of styrene derivatives using photoredox catalysts.1)

References

  • 1) Halogenated S-(perfluoroalkyl) dibenzothiophenium salt and its production methods
    • T. Umemoto, B. Zhang, T. Zhu, X. Zhou, Y. Li, PCT Int. Appl. WO 2016107578, 2016.
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