A common use of (CH3)3SiO3SCF3 is for the preparation of
silyl enol ethers.[3][4] One example involves the synthesis of the silyl enol ether of
camphor:
Trimethylsilyl trifluoromethanesulfonate has a variety of other specialized uses. It has been use to install tert-alkyl groups on phosphine (R = alkyl):[6]
PH3 + R3C–OAc + Me3SiOTf → [(R3C)2PH2]OTf
Deprotection of
Boc-protected amines can be achieved using trimethylsilyl trifluoromethanesulfonate and
triethylamine or
2,6-lutidine.[7][8]
TMSOTf is also a useful reagent to replace metal-halogen bonds with a covalent M-O(SO2CF3) bond, the by-product being the highly volatile TMSCl which is easily removed.
References
^Joseph Sweeney; Gemma Perkins; Enrique Aguilar; Manuel A. Fernández-Rodríguez; Rodolfo Marquez; Eric Amigues; Ricardo Lopez-Gonzalez (2018). "Trimethylsilyl Trifluoromethanesulfonate". Encyclopedia of Reagents for Organic Synthesis.
doi:
10.1002/047084289X.rt338.
ISBN978-0-471-93623-7.
^Kuehne, Martin E.; Xu, Feng (1 December 1998). "Syntheses of Strychnan- and Aspidospermatan-Type Alkaloids. 10. An Enantioselective Synthesis of (−)-Strychnine through the Wieland−Gumlich Aldehyde". The Journal of Organic Chemistry. 63 (25): 9427–9433.
doi:
10.1021/jo9813989.