79271-56-0 | Triethylsilyl trifluoromethanesulfonate

CAS:79271-56-0 | Triethylsilyl trifluoromethanesulfonate ,Description

Triethylsilyl trifluoromethanesulfonate (TES-TFMS) is an organosilicon compound which is widely used as a reagent in organic synthesis. It is a colorless liquid with a pungent odor and is soluble in organic solvents. This compound has been used in a variety of applications in the field of organic synthesis, such as the synthesis of chiral compounds, the preparation of enantiomerically pure compounds, and the synthesis of optically active compounds. TES-TFMS has also been used in the development of new synthetic methods and in the preparation of complex molecules.
 

Scientific Research Applications

Catalyst in Acylation Reactions

Triethylsilyl trifluoromethanesulfonate is an effective catalyst in acylation reactions. It is particularly useful for acylation of alcohols with acid anhydrides. This application is significant due to its efficiency and the ability to acylate a variety of alcohols including primary, secondary, tertiary, and allylic alcohols, as well as phenols, in a shorter time compared to standard conditions (Procopiou et al., 1998).

Use in Synthesis of Natural Products

Triethylsilyl trifluoromethanesulfonate plays a crucial role in the synthesis of natural products. It has been used in the Prins cyclization of acrylyl enol ethers, leading to the synthesis of natural products like (+)-civet (Sultana et al., 2013).

Catalyst in Reduction Reactions

This compound is also used in selective reduction reactions. Specifically, it aids in the reduction of hydroxy substituted carboxylic acids, ketones, and aldehydes to yield corresponding carbonyl compounds. This process is essential for various synthetic applications (Olah & Wu, 1991).

Lewis Acid Catalyst

Additionally, it functions as a Lewis acid catalyst. This characteristic is particularly advantageous in electrophilic aromatic substitution reactions, formation of carbon-carbon and carbon-heteroatom bonds, and in syntheses involving carbo- and heterocyclic structures (Kazakova & Vasilyev, 2017).

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