Trimethylsilyl trifluoromethanesulfonate (TMSOTf) is an organosilicon compound with the formula . It is a colorless moisture-sensitive liquid. It is the trifluoromethanesulfonate derivative of trimethylsilyl. It is mainly used to activate ketones and aldehydes in organic synthesis.
Reactions
TMSOTf is quite sensitive toward hydrolysis:
It is far more electrophilic than trimethylsilyl chloride.
Related to its tendency to hydrolyze, tmsOTf is effective for silylation of alcohols:
A common use of is for the preparation of silyl enol ethers. One example involves the synthesis of the silyl enol ether of camphor:
It was also used in Takahashi Taxol total synthesis and in chemical glycosylation reactions.
Trimethylsilyl trifluoromethanesulfonate has a variety of other specialized uses. I has been use to install tert-alkyl groups on phosphine (R = alkyl): PH3 + R3C–OAc + Me3SiOTf → [(R3C)2PH2]OTf
Deprotection of Boc-protected amines can be achieved using trimethylsilyl trifluoromethanesulfonate and triethylamine or 2,6-lutidine.