Regioselective iodination of activated arenes using KI-DMSO in aqueous hydrochloride

Abstract

The KI-DMSO in aqueous hydrochloride has been utilized for selective iodination of activated arenes. The iodination of substrate such as hydroxyacetophenones, amines, phenols, anisole and toluene took place with high regioselectivity and mono-iodination was found to occur. The electron releasing substituents (–CH3, –OCH3, –OH, –NH2) exclusively form para substituted product while ortho-iodination occurred only when para-position was blocked by other substituents. The method is simple and noteworthy for reactive arenes with comprises some advantages as easy reaction procedure, short reaction time (5–12 min.) and fair to good yield of aryl iodides (65–90%). The structure of aryl iodide was established on the basis of spectral and elemental data.

Keywords

• Activated arenes
• Regioselective iodination
• KI-DMSO