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Trifluoromethanesulfonyl chloride (or triflyl chloride, CF3SO2Cl) can be used in a highly efficient method to introduce a trifluoromethyl group to aromatic and heteroaromatic systems, including known pharmaceuticals such as Lipitor. The chemistry is general and mild, and uses a photoredox catalyst and a light source at room temperature. [27]
In organic chemistry, the triflyl group (systematic name: trifluoromethanesulfonyl group) is a functional group with the formula R−SO 2 CF 3 and structure R−S(=O) 2 −CF 3. The triflyl group is often represented by –Tf. The related triflate group (trifluoromethanesulfonate) has the formula R−OSO 2 CF 3, and is represented by –OTf. [1]
Trifluoromethyl group covalently bonded to an R group. The trifluoromethyl group is a functional group that has the formula-CF 3.The naming of is group is derived from the methyl group (which has the formula -CH 3), by replacing each hydrogen atom by a fluorine atom.
Trifluoromethanesulfonic anhydride, also known as triflic anhydride, is the chemical compound with the formula (CF 3 SO 2) 2 O. It is the acid anhydride derived from triflic acid. This compound is a strong electrophile, useful for introducing the triflyl group, CF 3 SO 2.
An example is the Mukaiyama aldol addition reaction between benzaldehyde and the silyl enol ether of cyclohexanone with an 81% chemical yield. [2] The corresponding reaction with the yttrium salt fails: Sc(OTf) 3-mediated aldol condensation. Triflate is a commonly used weakly coordinating anion. Use of Ni(OTf) 2 to facilitate C–H ...
Its pK a value in water cannot be accurately determined but in acetonitrile it has been estimated as −0.10 and in 1,2-dichloroethane −12.3 (relative to the pK a value of 2,4,6-trinitrophenol (picric acid), anchored to zero to crudely approximate the aqueous pK a scale [2]), making it more acidic than triflic acid (pK a MeCN = 0.70, pK a DCE ...
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Sulfonyl groups can be written as having the general formula R−S(=O) 2 −R′, where there are two double bonds between the sulfur and oxygen. [1]: 53 [2] Sulfonyl groups can be reduced to the sulfide with diisobutylaluminium hydride (DIBALH). Lithium aluminium hydride (LiAlH 4) reduces some but not all sulfones to sulfides. [1]: 1851