Studies on the Deprotection of Triisopropylsilylarylacetylene Derivatives

Several conditions to deprotect triisopropylsilylarylacety- lenes were examined. The triisopropylsilyl protecting group was ef- ficiently removed under mild conditions with 1.5 equiv. of AgF in methanol, a protocol recently reported by Kim. A mixture of AgNO3/ KF gave lower yields. Other conditions using combinations of a transi- tion metal, Cu(I), Co(II), Hg(II), and KF failed to react or produced decomposition. The AgF deprotection of TIPS-acetylenes allowed preparation of aryl and heteroaryl terminal alkynes.