S-(Trifluoromethyl)thianthrenium triflate (TT-CF3+OTf--) is a trifluoromethylating agent that can produce electrophilic, nucleophilic or radical CF3 moiety depending on conditions. The TT-CF3+OTf-- works as a universal trifluoromethylating agent that covers a wide scope of substrates. It is used to convert the alcohol group into fluorides, keto to CF2, and carboxylic into the fluoroacyl group. The substrate scope of the hydrotrifluoromethylation and the functional group tolerance of the TT-CF3+OTf- are large: esters, ethers, nitrogen heterocycles, and amides, as well as complex small molecules, are all tolerated. Moreover, styrene derivatives, which often engage in unproductive polymerization, isomerization, and dimerization, are tolerated in the transformation.
Synonyms: TT-CF3+OTf-, 5-(Trifluoromethyl)-5H-thianthren-5-ium trifluoromethanesulfonate