Silver trifluoromethanesulfonate, or silver triflate is the

triflate In organic chemistry, triflate ( systematic name: trifluoromethanesulfonate), is a functional group with the formula and structure . The triflate group is often represented by , as opposed to −Tf, which is the triflyl group, . For example, ...

(CF₃SO₃⁻) salt of Ag⁺. It is a white or colorless solid that is soluble in water and some organic solvents including,

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...

. It is a reagent used in the synthesis of organic and inorganic triflates.

Synthesis

An early preparation method starts from the barium salt of

trifluoromethanesulfonic acid Triflic acid, the short name for trifluoromethanesulfonic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF3SO3H. It is one of the strongest known acids. Triflic acid is mainly used in research as a catalyst for es ...

(TfOH), from which the free TfOH is formed with dilute sulfuric acid, which is then neutralized with

silver carbonate Silver carbonate is the chemical compound with the formula Ag2CO3. This salt is yellow but typical samples are grayish due to the presence of elemental silver. It is poorly soluble in water, like most transition metal carbonates. Preparation and ...

(Ag₂CO₃). :Ba^2+ SO2CF3 -> ce-\ce] CF3SO2OH -> ceCF3SO2O^- Ag+ The silver triflate is thereby obtained in a yield of 95% and can be recrystallized from

tetrachloromethane Carbon tetrachloride, also known by many other names (such as tetrachloromethane, also recognised by the IUPAC, carbon tet in the cleaning industry, Halon-104 in firefighting, and Refrigerant-10 in HVACR) is an organic compound with the chemica ...

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be ...

for purification. In an improved version by George Whitesides, dilute TfOH is reacted with silver(I)oxide (Ag₂O), which produces AgOTf in 98% yield.

Reactions

It is used to prepare alkyl triflates from alkyl halides: :CF₃SO₂OAg + RX → CF₃SO₂OR + AgX (X = iodide usually) In coordination chemistry, the salt is also useful to replace halide ligands with the more labile triflate ligand. For example, bromopentacarbonylrhenium can be converted to the more labile derivative using silver triflate: :CF₃SO₂OAg + BrRe(CO)₅ → CF₃SO₂ORe(CO)₅ + AgBr

References

{{silver compounds Silver compounds Triflates