Aerobic oxidative iodination of ketones catalysed by sodium nitrite “on water” or in a micelle-based aqueous system

Abstract

Selective and efficient aerobic oxidative iodination of ketones in aqueous media was achieved by using molecular iodine as the source of iodine atoms, air as the terminal oxidant, sodium nitrite (NaNO₂) as the catalyst and H₂SO₄ as the activator of the overall catalytic process. The efficiency of the reaction, resulting in α-iodo ketones, was significantly improved in an aqueous solution of the anionic amphiphile sodium dodecyl sulfate (SDS), capable of self-assembly into micelle-based aggregates, thus forming a reactive micellar system. The regioselectivity of iodofunctionalization of aryl methyl ketones was regulated by the reaction medium used: in an aqueous micelle-based system the methyl group was iodinated, while in anhydrous MeCN aryl iodides were formed with high selectvity.