27607-77-8 | Trimethylsilyl trifluoromethanesulfonate

CAS:27607-77-8 | Trimethylsilyl trifluoromethanesulfonate ,Description

Trimethylsilyl trifluoromethanesulfonate (TMS-TFMS) is a useful reagent in organic synthesis. It is a strong nucleophile which can be used as a catalyst in organic reactions. TMS-TFMS is also known as trifluoromethanesulfonate, trifluoromethanesulfonic acid, trifluoromethanesulfonimide, trifluoromethanesulfonic anhydride, and trifluoromethanesulfonyl chloride. It is commonly used in the synthesis of pharmaceuticals, agrochemicals, and other industrial chemicals. The reagent is also used in the synthesis of peptides, peptidomimetics, and other biomolecules. 
 

Scientific Research Applications

Catalyst for Acylation of Alcohols

TMSOTf acts as an efficient catalyst in the acylation of alcohols with acid anhydrides. This process is highly effective for various types of alcohols, including primary, secondary, tertiary, and allylic alcohols, as well as phenols, offering a cleaner and more efficient alternative to standard conditions (Procopiou et al., 1998).

Synthesis of Dihydropyrans

In the synthesis of dihydropyrans, TMSOTf is used for Prins cyclization of acrylyl enol ethers to 5,6-dihydro-2H-pyran-2-acetates. This method was effectively applied in the total synthesis of the natural product (+)-civet (Sultana et al., 2013).

Synthesis of N-Vinyl Derivatives of Nucleobases

TMSOTf is utilized for transforming vinyl acetate with pyrimidine and purine derivatives into vinyl nucleobases. This showcases the flexibility of TMSOTf as a Lewis acid catalyst (Dalpozzo et al., 2004).

Ring Opening of Oxiranes

TMSOTf promotes ring opening reactions of oxirane derivatives, leading to various transformation products depending on the substrate's structure (Murata et al., 1982).

Chemoselective Reactions of Acyclic Acetals

In the presence of cyclic acetals, TMSOTf facilitates chemoselective reactions of acyclic acetals with various reagents (Kim et al., 1994).

Isomerization of Nucleosides

TMSOTf catalyzes the isomerization of 3′,5′-O(tetraisopropyldisiloxane-1,3-diyl)nucleosides into 2′,3′-O(tetraisopropyldisiloxane-1,3-diyl)-derivatives (Kulikova et al., 2008).

Conversion of Aldehydes to Homoallyl Ethers

A mild method utilizing TMSOTf catalyzes the synthesis of homoallyl ethers from aldehydes in an ionic liquid. This process features several advantages, including the use of a recyclable ionic liquid and mild reaction conditions (Anzalone et al., 2005).

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