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Bulky Trialkylsilyl Acetylenes in the Cadiot−Chodkiewicz Cross-Coupling Reaction

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journal contribution
posted on 27.08.2002, 00:00 by Joseph P. Marino, Hanh Nho Nguyen
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.