Abstract

VALOIS ESCAMILLA, Ismael; RANGEL RAMOS, Luis Felipe; SANCHEZ ESCALERA, Javier  and  ALVAREZ HERNANDEZ, Alejandro. Studies on the Deprotection of Triisopropylsilylarylacetylene Derivatives. J. Mex. Chem. Soc [online]. 2011, vol.55, n.3, pp.133-136. ISSN 1870-249X.

Several conditions to deprotect triisopropylsilylarylacetylenes were examined. The triisopropylsilyl protecting group was efficiently 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 transition 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.

Keywords : Desylylation; silver fluoride; alkyne protecting group; TIPS-acetylene.

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