Nickel-catalyzed carbocyanation of alkynes with allyl cyanides

…, T Yukawa, N Kashihara, Y Nakao…

Index: Hirata, Yasuhiro; Yukawa, Tomoya; Kashihara, Natsuko; Nakao, Yoshiaki; Hiyama, Tamejiro Journal of the American Chemical Society, 2009 , vol. 131, # 31 p. 10964 - 10973

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Citation Number: 64

Abstract

Allyl cyanides are found to add across alkynes in the presence of a nickel/P (4-CF3− C6H4) 3 catalyst to give polysubstituted 2, 5-hexadienenitriles with defined stereo-and regiochemistry. Use of AlMe2Cl or AlMe3 as a Lewis acid cocatalyst accelerates the reaction and expands the substrate scope significantly. The cyano group in the allylcyanation products can be transformed to a hydroxymethyl or aminomethyl group to afford highly ...