Mechanisms of the reaction between benzonitrile and 4‐octyne catalyzed by Ni(PMe3)2: A theoretical investigation

Abstract

AbstractThe reaction mechanisms of benzonitrile and 4‐octyne catalyzed by Ni(PMe3)2 have been investigated using density functional theory (DFT) method at the B3LYP/6‐31+G(d,p) level, and the conductor‐like polarizable continuum model (CPCM) model was applied to simulate the solvent effect. The computational results suggest that benzonitrile has three possible paths to generate metallic intermediate. Then insertion and reductive elimination reactions happen between the metallic intermediate and 4‐octyne to yield the final product (Z)‐3‐phenyl‐2‐propyl‐2‐hexenenitrile. The analysis of frontier molecular orbital and electron density difference could help to reveal the substance of this reaction. And the results could provide valuable insights into these types of interactions and related ones.