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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1097-1107

Nickel-catalyzed carbocyanation of alkynes

Yoshiaki Nakao and Tamejiro Hiyama

Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan

Abstract: Nickel-catalyzed carbocyanation reaction of alkynes is described. Alkynes undergo aryl- and allylcyanation reaction in the presence of nickel-phosphine catalysts to give a wide range of substituted acrylonitriles in highly stereo-, regio-, and chemoselective manners. Lewis acid cocatalysts, such as AlMe3, AlMe2Cl, and BPh3, are found to promote the arylcyanation significantly. The cooperative catalysis of nickel and Lewis acid also allows the carbocyanation reaction using alkenyl and alkyl cyanides.