147531-11-1 | Diphenyl(trifluoromethyl)sulfoniumtrifluoromethanesulfonate

CAS:147531-11-1 | Diphenyl(trifluoromethyl)sulfoniumtrifluoromethanesulfonate ,Description

Diphenyl(trifluoromethyl)sulfoniumtrifluoromethanesulfonate (DFTMS) is a heterocyclic compound that has been extensively studied in recent years due to its unique properties. It has been used in a variety of chemical and biological applications, including synthesis, catalysis, and drug delivery. DFTMS is a powerful oxidizing agent and is highly reactive with a wide range of substrates. It is also a potent inhibitor of enzymes and has been used to study enzyme inhibition and to develop inhibitors for various biological targets. 
 

Scientific Research Applications

Generation of Trifluoromethylcarbene

Trifluoromethylcarbene (:CHCF3) is conveniently generated from diphenyl(trifluoromethyl)sulfonium triflate, applied in Fe-catalyzed cyclopropanation of olefins. This process yields trifluoromethylated cyclopropanes with high efficiency, showcasing the compound's role in introducing trifluoromethyl groups into organic frameworks (Duan et al., 2016).

Synthesis of Trifluoromethylsilanes

The compound facilitates magnesium metal-mediated reductive trifluoromethylation of chlorosilanes, using trifluoromethyl sulfides, sulfoxides, and sulfones. This innovative method underscores its potential in synthesizing trifluoromethylsilanes from environmentally benign trifluoromethane, catalytic in diphenyl disulfide (Prakash et al., 2003).

Cyclopropanation and Ring Transformation

(E)-Diphenyl-β-(trifluoromethyl)vinylsulfonium triflate, derived from diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate, undergoes alkylation with methylene compounds to produce trifluoromethylated cyclopropane derivatives. These derivatives are further transformed into trifluoromethylated dihydroaminothiophenes and aminothiophenes, demonstrating the compound's utility in complex molecular transformations (Kasai et al., 2012).

Biaryl Coupling Reactions

A sulfonium salt derived from diphenyl sulfoxide and trifluoromethanesulfonic anhydride has been developed for intermolecular biaryl coupling of phenol derivatives. This method facilitates rapid, one-pot reactions without leaving traces of the sulfonium moiety, extending its application to tri-substituted phenyl ethers (Higuchi et al., 2018).

Diastereoselective Synthesis

Diphenyl(trifluoromethyl)sulfonium triflate acts as an efficient ylide reagent in the Johnson-Corey-Chaykovsky reaction, yielding trifluoromethyl epoxides, cyclopropanes, and aziridines with notable diastereoselectivity. This highlights its role in synthesizing stereochemically complex fluorinated compounds (Duan et al., 2015).

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