Triethylsilyl trifluoromethanesulfonate

Chemical properties

clear colorless to light brown fuming liquid

Physical properties

85–86 °C/12 mmHg; d 1.169 g cm?3.

The Uses of Triethylsilyl trifluoromethanesulfonate

Triethylsilyl Trifluoromethanesulfonate can be used as potent silylating agent and as Lewis acid catalyst. Triethylsilyl ethers are generally more stable towards hydrolysis than are trimethylsilyl ethers, and consequently the Et3Si moiety has gained increasing use as a protecting group for alcohols. However, since it is often difficult to silylate sterically hindered hydroxyl groups using Et3SiCl, triethylsilyl perchlorate and triethylsilyl triflate (Et3SiOTf) were introduced to overcome this problem. Jefford has reported that condensation reactions of 2-trimethylsiloxyfuran with aldehydes can be catalyzed by Et3SiOTf to give mainly the threo addition product (eq 8).

The Uses of Triethylsilyl trifluoromethanesulfonate

Triethylsilyl trifluoromethanesulfonate acts as a silylating agent. It is also useful as a Lewis acid catalyst. Further, it reacts with 1-diazo-3,3-dimethyl-butan-2-one to prepare 1-diazo-3,3-dimethyl-1-(triethylsilyl)-2-butanone.

Preparation

Triethylsilyl Trifluoromethanesulfonate can be prepared by reacting chlorotriethylsilane with trifluoromethanesulfonic acid followed by distillation.