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Sustainable access to sulfonic acids from halides and thiourea dioxide with air
Green Chemistry ( IF 9.8 ) Pub Date : 2020-10-23 , DOI: 10.1039/d0gc03135f
Hui Zhang 1, 2, 3, 4, 5 , Ming Wang 1, 2, 3, 4, 5 , Xuefeng Jiang 1, 2, 3, 4, 5
Affiliation  

A sustainable and mild one-step strategy is explored for the synthesis of aryl and alkyl sulfonic acids using a facile combination of halides and sulfur dioxide surrogates under air. The cheap industrial material thiourea dioxide was employed as an eco-friendly and easy-handling sulfur dioxide surrogate, while air was used as a green oxidant. Both aryl and alkyl sulfonic acids were obtained under transition metal-catalyzed or transition metal-free conditions. Mechanistic studies demonstrated that sulfinate was involved as an intermediate in this transformation. Notably, this protocol has been applied to the late-stage sulfonation of the drugs naproxen, isoxepac and ibuprofen.

中文翻译:

空气可持续获取卤化物和二氧化硫脲中的磺酸

探索了一种可持续且温和的一步法,在空气中使用卤化物和二氧化硫代用品的简便组合来合成芳基和烷基磺酸。廉价的工业原料二氧化硫脲被用作一种生态友好,易于处理的二氧化硫替代物,而空气则被用作绿色氧化剂。芳基和烷基磺酸都在过渡金属催化或无过渡金属的条件下获得。机理研究表明,亚硫酸盐作为该转化的中间体。值得注意的是,该方案已被应用于萘普生,异氧平和布洛芬的后期磺化。
更新日期:2020-11-09
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