The non-natural trifluoromethyl group is of particular significance due to its biochemically important properties: namely, high electronegativity, stability, and lipophilicity. We developed S-(trifluoromethyl)-2,8-bis(trifluoromethoxy)dibenzothiophenium triflate (1, Umemoto reagent IV) that is a more powerful electrophilic trifluoromethylating agent than available previous versions. The reagent was synthesized from readily available, inexpensive 3,3’-bis(trifluoromethoxy)biphenyl by a one-pot method, consisting of 3 steps. The novel reagent (Umemoto reagent IV) proved substantially more powerful than the previous Umemoto reagent II (S-CF3-2,8-difluorodibenzothiophenium triflate) and displayed effective trifluoromethylation of a wide array of nucleophilic substrates. The characteristics of this novel reagent will make it useful in late stage trifluoromethylation of target compounds.

Synthesis and application of Umemoto reagent IV

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