Nickel-Catalyzed Addition of Alkynylboranes to Alkynes

Michinori Suginome,* Masamichi Shirakura, and Akihiko Yamamoto
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
J. Am. Chem. Soc., 2006, 128 (45), pp 14438–14439
DOI: 10.1021/ja064970j
Publication Date (Web): October 24, 2006
Copyright © 2006 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.

, suginome@sbchem.kyoto-u.ac.jp

Abstract

Abstract Image

Alkynylboration has been achieved in the reaction of alkynyl(pinacol)boranes with alkynes in the presence of nickel catalysts, giving cis-1-borylbut-1-en-3-yne derivatives. 1-Aryl-1-alkynes underwent the alkynylboration regioselectively with the selective introduction of the alkynyl groups at their 1-positions, where the aryl groups were attached. The boryl-substituted enynes were reacted with sp2 halides under the Suzuki−Miyaura coupling conditions, giving highly conjugated enynes in high yields.

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History

  • Published In Issue November 15, 2006
  • Received July 12, 2006

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