Trifluoromethanesulfonic anhydride

Description

Trifluoromethanesulfonic anhydride, also known as triflic anhydride, has proven to be an extraordinary reagent for a broad range of transformations. As a commercially and readily available reagent, It has been widely used in synthetic chemistry due to its high electrophilicity.

Chemical properties

clear colorless to light brown liquid

The Uses of Trifluoromethanesulfonic anhydride

Trifluoromethanesulfonic Anhydride is a strong electrophile used in chemical synthesis for introducing the triflyl group. Trifluoromethanesulfonic anhydride is used to convert phenols and imine into triflic ester and NTf group. It serves as a reagent in the preparation of alkyl and vinyl triflates, and for the stereoselective synthesis of mannosazide methyl uronate donors. It acts as a catalyst for glycosylation with anomeric hydroxy sugars to prepare polysaccharides.

Definition

ChEBI: Triflic anhydride is an organosulfonic anhydride. It is functionally related to a triflic acid.

Hazard

May be corrosive to metals. Harmful if swallowed. Causes severe skin burns and eye damage.

Storage

Store in a cool, dry, wellventilated area.  Moisture sensitive.

Purification Methods

It can be freshly prepared from the anhydrous acid (11.5g) and P2O5 (11.5g, or half this weight) by setting aside at room temperature for 1hour, distilling off volatile products then distil it through a short Vigreux column. It is readily hydrolysed by H2O and decomposes appreciably after a few days to liberate SO2 and produce a viscous liquid. Store it dry at low temperatures. [Burdon et al. J Chem Soc 2574 1957, Beard et al. J Org Chem 38 373 1973, Beilstein 3 IV 35.]

References

[1] Haoqi Zhang. “Trifluoromethanesulfonic Anhydride in Amide Activation: A Powerful Tool to Forge Heterocyclic Cores.” TCIMAIL (2021).
[2] Dr. Qixue Qin, Prof. Dr. Ning Jiao, Zengrui Cheng. “Recent Applications of Trifluoromethanesulfonic Anhydride in Organic Synthesis.” Angewandte Chemie 135 10 (2022).