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DOI: 10.1055/s-0032-1317176
Umemoto’s Reagent
Publikationsverlauf
Publikationsdatum:
03. September 2012 (online)
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Introduction
The trifluoromethyl group is an important structural moiety in diverse organic molecules due to the significant unique features that trifluoromethylated compounds have in pharmaceuticals, agricultural chemicals, and functional materials.[ 1 ]
The first electrophilic trifluoromethylating reagent, diaryl(trifluoromethyl) sulfonium salt, Ar2S+CF3SbF6 −, was achieved by Yagupolskii and co-workers in 1984.[ 2 ] In 1990, Umemoto and co-workers developed a new series of electrophilic trifluoromethylating reagents, for example, (trifluoromethyl)dibenzoheterocyclic salts with fine tuning of their electrophilicity.[3] [4] [5] The reagents are achieved via an oxidation of the starting materials (sulfides, selenides or telluride) followed by a cyclization or a direct fluorination (Scheme [1]). As an efficient electrophilic trifluoromethylating agent, Umemoto’s reagent has been successfully applied in the trifluoromethylation of a wide range of nucleophiles including carbanions, silyl enol ethers, enamines, phenols, anilines, phosphines and thiolates. The combination of Umemoto’s reagent with a chiral base provided a useful entry to the enantioselective electrophilic trifluoromethylation. More recently, the direct C–H bond trifluoromethylation has been achieved by using the Umemoto’s reagent and transition-metal catalysis, thus expanding the scope of current popular C–H bond activations.
Umemoto’s reagents are operational simple, high stabile at ambient conditions and commercially available.
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