Palladium-Catalyzed Selective Cross-Addition of Triisopropylsilylacetylene to Internal and Terminal Unactivated Alkynes

Naofumi Tsukada,* Satoshi Ninomiya, Yoshimi Aoyama, and Yoshio Inoue*
Graduate School of Engineering, Tohoku University, Sendai 980-8579, Japan
Org. Lett., 2007, 9 (15), pp 2919–2921
DOI: 10.1021/ol071326g
Publication Date (Web): June 28, 2007
Copyright © 2007 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.

, tsukada@aporg.che.tohoku.ac.jp

Abstract

Abstract Image

Dinuclear and mononuclear palladium complexes having N,N‘-bis[2-(diphenylphosphino)phenyl]amidinate (DPFAM) as a ligand catalyzed the cross-addition of triisopropylsilylacetylene (TIPSA) to unactivated internal alkynes, giving enynes selectively. When palladium catalysts having PPh3, TDMPP, dppe, or dppf were used, dimers of TIPSA were obtained as major products. The reactions of TIPSA with several terminal alkynes also gave cross-adducts selectively, although the yields were moderate.

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History

  • Published In Issue July 19, 2007
  • Received June 5, 2007

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