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

Joseph P. Marino*† and Hanh Nho Nguyen
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109 jmarino@nd.edu
J. Org. Chem., 2002, 67 (19), pp 6841–6844
DOI: 10.1021/jo025745x
Publication Date (Web): August 27, 2002
Copyright © 2002 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
†

 Current address:  Department of Chemistry, University of Notre Dame, Notre Dame, IN 46556-0069.

Abstract

Abstract Image

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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History

  • Published In Issue September 20, 2002
  • Received March 21, 2002

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