Allylcyanation of Alkynes:  Regio- and Stereoselective Access to Functionalized Di- or Trisubstituted Acrylonitriles

Yoshiaki Nakao,* Tomoya Yukawa, Yasuhiro Hirata, Shinichi Oda, Jun Satoh, and Tamejiro Hiyama*
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan
J. Am. Chem. Soc., 2006, 128 (22), pp 7116–7117
DOI: 10.1021/ja060519g
Publication Date (Web): May 16, 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.

, nakao@npc05.kuic.kyoto-u.ac.jp, thiyama@npc05.kuic.kyoto-u.ac.jp

Abstract

Abstract Image

Allyl cyanides are found to add across alkynes in the presence of a nickel catalyst prepared from Ni(cod)2 and P(4-CF3−C6H4)3 in situ to give variously functionalized di- or trisubstituted acrylonitriles in highly stereoselective manners possibly via a π-allylnickel species as an intermediate. α-Siloxyallyl cyanides also react at the γ-position of a cyano group with both internal and terminal alkynes having various functional groups to give silyl enol ethers, which give the corresponding aldehydes or ketones upon hydrolysis.

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History

  • Published In Issue June 07, 2006
  • Received January 23, 2006

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