An environmentally friendly, operationally simple and convenient, scalable, temperature- and solvent-directed oxidation of hydrophobic sulfides that yields sulfoxides and sulfones is presented. The conversion proceeds rapidly in a variety of green solvents, e.g., methanol, water, acetone, and acetic acid using tert-butyl hypochlorite (t-BuOCl), an easy-to-prepare and inexpensive oxidant with numerous applications in green chemistry and industry. Oxidation proceeds efficiently for challenging and purely soluble perfluoroalkyl, heterocyclic, or polyaryl systems with multiple strongly electron-withdrawing groups, e.g. nitro, acyl, and chloro, and selectively for electron-rich systems with benzylic and enolizable competing reaction sites or multiple sulfur atoms. Various industrially important products such as pesticides, anti-HIV agents, polymer monomers and additives can be generally isolated in pure form by simply removing the reaction solvent and benign volatiles. The mechanism was explored by NMR experiments and DFT calculations. Selective oxidation of polyphenylene sulfide allowed us to synthesize more durable polymer powders and to modify the surface of the film. The depth of the oxidized layer was tuned by duration of exposure to the oxidant. The developed clean, rapid, preparative, and scalable transformation of sulfides generally without required purification can likely be extended to other similar substrates and might be of interest for synthetic and sustainability-oriented chemical processes.

中文翻译：

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使用 t-BuOCl 对二芳基硫化物进行便捷、无需金属、无需提取且通常无需纯化、温度和溶剂定向的氧化


提出了一种环保、操作简单、方便、可扩展、温度和溶剂导向的疏水性硫化物氧化法，可产生亚砜和砜。使用次氯酸叔丁酯 （t-BuOCl） 在各种绿色溶剂中快速进行转化，例如甲醇、水、丙酮和乙酸，次氯酸叔丁酯 （t-BuOCl） 是一种易于制备且价格低廉的氧化剂，在绿色化学和工业中有多种应用。对于具有多个强吸电子基团的具有挑战性且完全可溶的全氟烷基、杂环或聚芳基体系，氧化可以有效地进行，例如硝基、酰基和氯，以及选择性地用于具有苄基和可烯醇化竞争反应位点或多个硫原子的富电子体系。各种工业上重要的产品，如杀虫剂、抗 HIV 剂、聚合物单体和添加剂，通常可以通过简单地去除反应溶剂和良性挥发物以纯形式分离。通过 NMR 实验和 DFT 计算探索了其机制。聚苯硫醚的选择性氧化使我们能够合成更耐用的聚合物粉末并改性薄膜表面。氧化层的深度通过暴露于氧化剂的持续时间进行调整。通常无需纯化即可开发的清洁、快速、制备和可扩展的硫化物转化方法可以扩展到其他类似的底物，并且可能对合成和以可持续性为导向的化学过程感兴趣。