Nickel/AlMe2Cl-catalysed carbocyanation of alkynes using arylacetonitriles

Akira Yada; Tomoya Yukawa; Yoshiaki Nakao; Tamejiro Hiyama

doi:10.1039/B907290J

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Nickel/AlMe₂Cl-catalysed carbocyanation of alkynes using arylacetonitriles†‡

Akira Yada,^a Tomoya Yukawa,^a Yoshiaki Nakao*^a and Tamejiro Hiyama*^a

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^a Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan
E-mail: yoshiakinakao@npc05.mbox.media.kyoto-u.ac.jp, thiyama@z06.mbox.media.kyoto-u.ac.jp
Fax: +81 75 383 2445
Tel: +81 75 383 2446

Abstract

Nickel/Lewis acid dual catalysis was found to effect the carbocyanation reaction of alkynes using arylacetonitriles, giving a range of triply substituted acrylonitriles; the reaction of optically active α-phenylpropionitrile suggested a reaction mechanism that involves oxidative addition of a C–CN bond with retention of its absolute configuration.

This article is part of the themed collection: Selective Catalysis for Organic Synthesis

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Article information

DOI: https://doi.org/10.1039/B907290J
Article type: Communication
Submitted: 18 ربيع الثاني 1430
Accepted: 10 جمادى الأولى 1430
First published: 02 جمادى الثانية 1430

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Chem. Commun., 2009, 3931-3933

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Nickel/AlMe₂Cl-catalysed carbocyanation of alkynes using arylacetonitriles

A. Yada, T. Yukawa, Y. Nakao and T. Hiyama, Chem. Commun., 2009, 3931 DOI: 10.1039/B907290J

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Chemical Communications