Iodine-Promoted Controlled and Selective Oxidation of (Aryl)(Heteroaryl)Methanes

Abstract

The development of direct and controlled oxidation of C(sp3)–H bonds is of great importance. Herein, an iodine-catalyzed controlled oxidation of (aryl)(heteroaryl)methanes to (aryl)(heteroaryl)methanols is disclosed under metal-free reaction conditions. A catalytic system comprised of iodine/silyl chloride with HI as an additive in the presence of dimethyl sulfoxide selectively oxidizes the C(sp3)–H bonds without being overoxidized to corresponding ketones. Therapeutically important aryl heteroaryl methanol derivatives were obtained in good yields. The preliminary mechanistic investigation proves that the primary source of oxygen is DMSO.

Topics & Concepts