Influence of substrate structure on copper(I)-assisted cyanide substitution in aryl halides

Abstract

The synthesis of various aryl halides is described: these are designed to explore the structural characteristics which are sufficient to enable copper(I)-assisted substitution of the halide by cyanide to proceed. The copper ion serves to polarise the substrate; stable co-ordination complexes are not formed. The role of various heteroatoms in the substrate is assessed and the importance of intramolecular hydrogen bonding is established.