Iodine-Promoted Controlled and Selective Oxidation of (Aryl)(Heteroaryl)Methanes
Somraj Guha1, Imran Kazi1, Dhamodharan Sathish1
1Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu 600 036, India.
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.
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