1885-46-7 | Difluoromethyl trifluoromethanesulfonate

CAS:1885-46-7 | Difluoromethyl trifluoromethanesulfonate ,Description

Difluoromethyl trifluoromethanesulfonate (DFTMS) is a powerful fluorinating agent that has been used in a variety of industrial and scientific applications. DFTMS is a highly reactive compound that can be used to synthesize various compounds, including organofluorines, and has been used in a variety of laboratory experiments. It is a versatile reagent that can be used to introduce fluorine atoms into organic molecules, as well as to initiate and catalyze a variety of reactions.
 

Scientific Research Applications

• Catalysis in Organic Synthesis:Difluoromethyl trifluoromethanesulfonate is used as a catalyst in organic synthesis. For instance, scandium trifluoromethanesulfonate is a highly active Lewis acid catalyst used in the acylation of alcohols with acid anhydrides and in the esterification of alcohols by carboxylic acids. This catalyst is especially effective in selective macrolactonization of omega-hydroxy carboxylic acids (Ishihara et al., 1996).
• Organic Synthesis and Electrophilic Reactions:Trifluoromethanesulfonic acid, closely related to difluoromethyl trifluoromethanesulfonate, plays a crucial role in electrophilic aromatic substitution reactions, the formation of carbon-carbon and carbon-heteroatom bonds, and in syntheses of carboand heterocyclic structures (Kazakova & Vasilyev, 2017). Additionally, trifluoromethanesulfonic (triflic) acid serves as an excellent catalyst in 5-endo cyclization reactions to form pyrrolidines and other polycyclic systems (Haskins & Knight, 2002).
• Applications in Vinyl and Aryl Triflates Synthesis:The synthesis and applications of vinyl and aryl trifluoromethanesulfonates (triflates), which are easily prepared from carbonyl compounds and phenols, are significant. They are used in cross-coupling reactions with organo-metallics and in addition reactions to alkenes and alkynes, with specific applications in natural product synthesis (Ritter, 1993).
• Medicinal Chemistry and Material Science:Derivatives of tetrafluoroethane β-sultone, related to difluoromethyl trifluoromethanesulfonate, are employed as versatile difluoromethylation and trifluoromethylation reagents. These derivatives have applications in the design of drug candidates and the synthesis of novel functional materials (Zhang et al., 2014).
• Friedel-Crafts Alkenylation Reactions:Metal trifluoromethanesulfonates are catalysts in Friedel-Crafts alkenylation of arenes using alkynes, leading to the formation of 1,1-diarylalkenes. These reactions occur through an alkenyl cation intermediate (Tsuchimoto et al., 2000) .
• Aminolysis of 1,2-Epoxides:Lanthanide(III) trifluoromethanesulfonates, such as Yb(OTf)3, Nd(OTf)3, and Gd(OTf)3, are highly efficient catalysts for the aminolysis of 1,2-epoxides, producing β-amino alcohols with high selectivity and yield (Chini et al., 1994).
• Synthetic Applications in Click Chemistry:Trifluoromethyl trifluoromethanesulfonate has been employed as an effective reservoir of difluorophosgene in click chemistry applications for the preparation of urea derivatives, heterocycles, and carbamoyl fluorides. This method offers rapid, efficient, selective, and versatile reactions (Song et al., 2019).
• Acid-Catalyzed Reactions:Trifluoromethanesulfonic acid is a superior catalyst for acylation, demonstrating unique controllability in C-acylation and/or O-acylation reactions (Tachrim et al., 2017).

More Information