Bulky trialkylsilyl acetylenes in the Cadiot-Chodkiewicz cross-coupling reaction.

J Org Chem

Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.

Published: September 2002

Bulky trialkylsilyl-protected alkynes such as triethylsilyl (TES), tert-butyldimethylsilyl (TBS), and triisopropylsilyl (TIPS) acetylenes underwent the Cadiot-Chodkiewicz cross-coupling reaction with different bromoalkynes to form a variety of synthetically useful unsymmetrical diynes in good yields. The diyne alcohol 10 was transformed regio- and stereoselectively into enynes by hydrotelluration, carbometalation, and reduction reactions.

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http://dx.doi.org/10.1021/jo025745xDOI Listing

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