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Synthesis 2009(12): 1963-1968  
DOI: 10.1055/s-0029-1216788
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Deprotection of Bulky (Trialkylsilyl)acetylenes with Silver Fluoride

Sanghee Kim*, Bogyeong Kim, Jinkyung In
College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea
Fax: +82(2)8880649; e-Mail: pennkim@snu.ac.kr;
Further Information

Publication History

Received 13 January 2009
Publication Date:
30 April 2009 (online)

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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.

Key words

desilylation - trialkylsilyl - silver fluoride - chemoselectivity - alkynes

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