The Copper(I) Iodide-assisted Reaction of Nonactivated Aryl Iodides with Some Alkali Metal Pseudohalides

Article abstract of DOI:10.1246/bcsj.53.1765

Copper(I) iodide dissolves into warm hexamethylphosphoric triamide to give a black solution, in which polymethylated iodobenzenes undergo nucleophilic attack by azide and selenocyanate ions, giving the corresponding aryl azides and selenocyanates in low to good yields.In the absence of copper(I) salt, however, the reaction does not take place.Cyanide, cyanate, thiocyanate, and fluoride ions bring about a decoloration of the reaction mixture and no displacement reactions ensue, while the tellurocyanate ion affords the corresponding aryl cyanides while liberating elemental tellurium.