Triflate

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Triflate, more formally known as trifluoromethanesulfonate, is a functional group with the formula CF₃SO₃-. The triflate radical is often represented by -OTf, as opposed to -Tf for the trifyl radical, CF₃SO₂-. For example, the n-butyl triflate, CH₃CH₂CH₂CH₂OTf.

The triflate anion, CF₃SO₃^- is an extremely stable polyatomic ion, being the conjugate base of triflic acid (CF₃SO₃H), one of the strongest acids known as a super acid.

[edit] Applications

A triflate group is an excellent leaving group used in certain organic reactions such as nucleophilic substitution, Suzuki couplings and Heck reactions. Since alkyl triflates are extremely reactive in S_N2 reactions, they must be stored in conditions free of nucleophiles (such as water).

Lithium triflates are used in some lithium ion batteries as a component of the electrolyte.

A mild triflating reagent is phenyl triflimide or N,N-bis(trifluoromethylsulfonyl)aniline, where the by-product is [CF₃SO₂N-Ph]^-.

[edit] See also

• trifluoromethanesulfonic acid