Alkenenitriles: Zn-Cu promoted conjugate additions of alkyl iodides in water

Abstract

A new silica-supported zinc-copper matrix dramatically promotes conjugate additions of alkyl iodides to alkenenitriles in water. Acyclic and cyclic nitriles react with functionalized alkyl iodides, overcoming the previous difficulty of performing conjugate additions to disubstituted alkenenitriles with nonstabilized carbon nucleophiles. Conjugate additions with ω-chloroalkyl iodides generate cyclic nitriles primed for cyclization, collectively providing one of the few annulation methods for cyclic alkenenitriles. © 2006 American Chemical Society.