Trifluoromethylsulfonyl

As triflyl the covalently bonded rest of trifluoromethanesulfonic acid ( CF3SO3 - ) is called organic compounds. It thus concerns the esters of trifluoromethanesulfonic acid. Your name is derived from its systematic name trifluoromethanesulfonyl. The compounds are commonly referred to as triflates and should not be confused with the same salts of trifluoromethanesulfonic acid ( triflates ). In the structural formulas triflyl is usually abbreviated with Tf or OTf. It is structurally related to the mesyl group.

Production

Triflates may be prepared by deprotonation of an alcohol and subsequent reaction with trifluoromethanesulfonyl chloride, with one equivalent of hydrogen chloride is bound by a base as the hydrochloride:

Properties

By the negative inductive effects of the fluorine atoms, the sulfur and oxygen atoms are electron poor. In addition, the triflate three limiting structures is well resonance-stabilized. This results in that the triflic acid is a strong acid and thus, the triflate anion is a weak base, which can be easily eliminated by suitable nucleophiles under substitution. For this reason, Triflylverbindungen in the absence of nucleophiles, such as water or alcohols, are kept.

Use

The triflyl is an excellent leaving group and is used as such an application in preparative organic chemistry. The conversion of alcohols into triflates the poor leaving group OH in converting a good leaving group, thereby substitution reactions are made possible at this position. Triflates here are up to 10,000 times more reactive than tosylates.

This application is not very atom economical, as always, stoichiometric quantities of waste materials are formed with relatively high molecular mass. Therefore, the synthesis method is mainly used in laboratory scale and scarcely in industrial processes.

With alcohols form ethers alkyl triflates in the sense of Williamson ether synthesis.

Palladium -catalyzed reaction such as the Suzuki or Sonogashira coupling aryl or Alkenyltriflate can be used instead of the halogen compounds are often used. The series of reactivity of aryl compounds is here:

11C -labeled methyl triflate is used for the introduction of labeled methyl groups in biological molecules.