Wang Ming, Zhao Jiaoyan, Jiang Xuefeng
Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062, P.R. China.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P.R. China.
ChemSusChem. 2019 Jul 5;12(13):3064-3068. doi: 10.1002/cssc.201802919. Epub 2019 Feb 12.
A three-component cross-coupling protocol of boronic acid, sodium metabisulfite, and dimethyl carbonate was developed for the construction of significant functional methyl sulfones, in which introduction of sulfur dioxide at the last stage was successfully achieved in one step. Inorganic sodium metabisulfite was used as an eco-friendly sulfur dioxide source. Green dimethyl carbonate was employed as methyl reagent in this transformation. Diverse functional methyl sulfones were obtained from various readily available boronic acids. Notably, the last-stage modification of pharmaceuticals and the synthesis of Firocoxib were efficiently established through this strategy.
开发了一种硼酸、焦亚硫酸钠和碳酸二甲酯的三组分交叉偶联方案,用于构建重要的功能性甲基砜,其中在最后阶段成功一步实现了二氧化硫的引入。无机焦亚硫酸钠用作环保型二氧化硫源。绿色碳酸二甲酯在该转化中用作甲基试剂。从各种容易获得的硼酸中获得了多种功能性甲基砜。值得注意的是,通过该策略有效地实现了药物的最后阶段修饰和非甾体抗炎药菲罗考昔的合成。