Silver trifluoromethanesulfonate, or silver triflate is the

triflate In organic chemistry, triflate (Preferred IUPAC name, systematic name: trifluoromethanesulfonate), is a functional group with the Chemical formula, formula and Chemical structure, structure . The triflate group is often represented by , as opp ...

(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 compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...

. It is a

reagent In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...

used in the synthesis of organic and inorganic triflates.

Synthesis

An early preparation method starts from the

barium Barium is a chemical element; it has symbol Ba and atomic number 56. It is the fifth element in group 2 and is a soft, silvery alkaline earth metal. Because of its high chemical reactivity, barium is never found in nature as a free element. Th ...

salt of trifluoromethanesulfonic acid (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 Ag2 C O3. 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 a ...

(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 carbon tet for short and tetrachloromethane, also IUPAC nomenclature of inorganic chemistry, recognised by the IUPAC), is a chemical compound with the chemical formula CCl4. It is a n ...

ether In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R� ...

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 A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of chemical bond, bound molecules or ions, that are in turn known as ' ...

, 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