Conjugate Addition of Alkyl Iodides to Alkenenitriles in Water

Significance

Unsaturated nitriles are attractive intermediates in organic chemistry due to the high synthetic utility of a nitrile group. However, a conjugate addition reaction to alkenenitriles is often difficult to perform. Herein, a convenient method for the conjugate addition of simple alkyl iodides to cyclic and acyclic disubstituted alkenenitriles is described. The reaction is performed in water at ambient temperature, the isolation of the products is straightforward and good yields are achieved. The addition products are suitable, for instance, for further intramolecular anionic cyclizations resulting in the formation of various cyano-substituted bicyclic ring systems.