Reaction of Aryl Iodides with Arenethiolates, -selenolates, and -tellurolates as a Simple Route to Unsymmetrically Polysubstituted Diary! Sulfides, Selenides, and Tellurides

Abstract

Copper ( I ) iodide dissolves in hot hexamethylphosphoric triamide (HMPA) to form a black solution, in which nonactivated aryl iodides readily underwent nucleophilic attack by benzenethiolate and benzeneselenolate ions, giving the corresponding diaryl sulfides and selenides in moderate to good yields. Without copper ( I ) salt, no substitution reaction took place. Under similar conditions, benzenetellurolate ion could also react with moderately activated aryl iodides to produce diaryl tellurides in fair to good yields. The present reaction provides a simple convenient route to unsymmetrically polysubstituted diaryl sulfides, selenides, and tellurides, which are laboriously obtained by the ordinary procedures.