Facile Deprotection of Bulky (Trialkylsilyl)acetylenes with Silver Fluoride

Abstract

An efficient and mild method is developed for the deprotection of bulky (trialkylsilyl)acetylenes. Treatment of 1-(triisopropylsilyl)acetylenes with silver fluoride, followed by hydrolysis of the intermediate silver acetylide with organic or inorganic acids, produces terminal acetylenes in good to excellent yields. The reactions­ are chemoselective and various functional groups are tolerated­.

desilylation - trialkylsilyl - silver fluoride - chemoselectivity - alkynes

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