ChemicalBook > Articles Catagory List >Organic-Chemistry >trimethylsilyl-trifluoromethanesulfonate-a-versatile-reagent-in-modern-organic-synthesis

Trimethylsilyl Trifluoromethanesulfonate: A Versatile Reagent in Modern Organic Synthesis

Oct 24，2024

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) is a colorless moisture-sensitive liquid, it is frequent catalyzer or cationic initiator as silylation reagent in organic synthesis.

Article illustration

Properties

The trimethylsilyl trifluoromethanesulfonate (TMSOTf) promoted β-lactam fragmentation of 4-alkylthioazetidin-2-ones demonstrates a novel method to access N,S-acetals in moderate-to-excellent yields <1996JCS(P1)2321>. The reaction occurs by a nucleophilic attack of a nitrile group on the generated cation intermediate. 1

Applications

Trimethylsilyl Trifluoromethanesulfonate is mainly used to activate ketones and aldehydes in organic synthesis.

Preparation

The preparation method of Trimethylsilyl Trifluoromethanesulfonate:

in reaction vessel, add anhydrous trifluoromethanesulfonic acid and anhydrous trimethylchlorosilane; stirring reaction 12h under protection of inert gas; temperature of reaction is 10 ℃～30 ℃; after reaction finishes, underpressure distillation 1-2h, collects 125-135 ℃ of cut and is Trimethylsilyl Trifluoromethanesulfonate.

References

[1] Stark, Holger. “Book Review: Comprehensive Organic Functional Group Transformations II by Alan Katritzky and Richard Taylor.”Archiv der Pharmazie 338 11 (2005): 565.

);