Триизопропилсилилтрифторметансульфонат

clear light brown to orange-brown liquid

Colorless oil; bp 83–87 °C/1.7 mmHg; d 1.173 g cm?3.

Triisopropylsilyl Trifluoromethanesulfonate is a highly reactive silylating agent and Lewis acid capable of converting primary and secondary alcohols to the corresponding triisopropylsilyl ethers and converting ketones and lactones into their enol silyl ethers; protection of terminal alkynes; promoting conjugate addition of alkynylzinc compounds to α,β-enones; preparation of (triisopropylsilyl)diazomethane, participating in the following (but not limited to) reactions: Silylation of Alcohols, Formations of Enol Silyl Ethers, Alkynyltriisopropylsilanes, Conjugate Addition of Alkynylzinc Bromides, (Triisopropylsilyl)diazomethane, Triisopropylsiloxycarbonyl (Tsoc) and BIPSOP Protecting Groups for Amines, TIPS Protection for Oxazoles/Regioselective Trapping of C-2 Oxazole Anions, Benzannulation Using Triisopropylsilyl Vinyl Ketenes, Cyclization of 1-Silyloxy-1,5-diynes, Desymmetrization of Tartaric Acid Esters etc.

To 38.2 g (0.242 mol) of triisopropylsilane at 0°C under argon is added 23.8 mL (0.266 mol) of trifluoromethanesulfonic acid dropwise. The solution is stirred at 22°C for 16 h, at which time no further hydrogen gas evolves (removed through a bubbler). The resulting product is distilled through a 30-cm vacuum jacketed Vigreux column under reduced pressure: 71.7 g (97% yield) of TIPS triflate; bp 83–87°C/1.7 mmHg.

Triisopropylsilyl Trifluoromethanesulfonate is a highly reactive silylating agent and Lewis acid capable of converting primary and secondary alcohols to the corresponding triisopropylsilyl ethers and converting ketones and lactones into their enol silyl ethers; protection of terminal alkynes; promoting conjugate addition of alkynylzinc compounds to α,β-enones; preparation of (triisopropylsilyl)diazomethane).