Studies on the Deprotection of Triisopropylsilylarylacetylene Derivatives
DOI:
https://doi.org/10.29356/jmcs.v55i3.810Keywords:
Desylylation, silver fluoride, alkyne protecting group, TIPS-acetylene.Abstract
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.Downloads
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