The Cyanation of Vinyl Halides with Alkali Cyanides Catalyzed by Nickel (0)-Phosphine Complexes Generated In Situ: Synthetic and Stereochemical Aspects.

Y Sakakibara, H Enami, H Ogawa, S Fujimoto…

Index: Sakakibara, Yasumasa; Enami, Hiroji; Ogawa, Hiroshi; Fujimoto, Shinpei; Kato, Hiroyuki; et al. Bulletin of the Chemical Society of Japan, 1995 , vol. 68, # 11 p. 3137 - 3144

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Citation Number: 17

Abstract

The cyanation of β-bromostyrenes catalyzed by Ni (PPh 3) n, which was generated in situ from NiBr 2 (PPh 3) 2–Zn–PPh 3 (Ni: Zn: P= 1: 3: 2 molar ratio), was at first examined with various MCN (M= K, Na)-dipolar aprotic solvent systems by several procedures. The presence of excess cyanide ion inhibited the reaction. However, when the KCN–DMF system with some intermediate cyanide solubility was used, the nitriles were obtained in ...