A Dramatic Effect of Lewis-Acid Catalysts on Nickel-Catalyzed Carbocyanation of Alkynes

Yoshiaki Nakao,* Akira Yada, Shiro Ebata, and Tamejiro Hiyama*;
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan
J. Am. Chem. Soc., 2007, 129 (9), pp 2428–2429
DOI: 10.1021/ja067364x
Publication Date (Web): February 13, 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.

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

Abstract

Abstract Image

Lewis-acid catalysts such as AlMe3, AlMe2Cl, and BPh3 significantly improve the efficiency of the nickel-catalyzed arylcyanation of alkynes. Electron-rich aryl cyanides, which exhibit poor reactivity in the absence of Lewis acids, readily undergo the arylcyanation reaction under the newly disclosed conditions. Excellent chemoselectivity is observed for aryl cyanides having a chloro and bromo group, allowing a single-step preparation of the synthetic intermediate of P-3622, a squalene synthetase inhibitor. Moreover, the first examples of alkenyl- and alkylcyanation of alkynes have been achieved by the nickel−Lewis acid dual catalyst.

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History

  • Published In Issue March 07, 2007
  • Received October 13, 2006

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