Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu 600 036, India.
J Org Chem. 2022 Apr 15;87(8):5424-5429. doi: 10.1021/acs.joc.1c03067. Epub 2022 Mar 31.
The development of direct and controlled oxidation of C-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-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.
C-H 键的直接和可控氧化的发展具有重要意义。在此，在无金属反应条件下，公开了一种碘催化的（芳基）（杂芳基）甲烷到（芳基）（杂芳基）甲醇的可控氧化。由碘/氯化硅与 HI 作为添加剂在二甲基亚砜存在下组成的催化体系可选择性地氧化 C-H 键，而不会过度氧化成相应的酮。得到了具有良好收率的治疗上重要的芳基杂芳基甲醇衍生物。初步的机理研究证明，氧的主要来源是 DMSO。
