The Journal of organic chemistry

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

JP Marino, HN Nguyen

Index: Marino, Joseph P.; Nguyen, Hanh Nho Journal of Organic Chemistry, 2002 , vol. 67, # 19 p. 6841 - 6844

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Citation Number: 96

Abstract

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.