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Transition‐Metal‐Free Perfluoroalkylation of N‐Thiophthalimides or N‐Thioimides to Access Perfluoroalkyl Sulfides
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-06-21 , DOI: 10.1002/ejoc.202400542
Wenting Liu 1 , Han Qian 1 , Zijie Song 1 , Yong Liu 1 , Jiajian Peng 1 , Wen-Wu Sun 2 , xinxin shao 3 , Ying Bai 1
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A practical and efficient trifluoromethylation of readily available and bench stable N‐Thiophthalimides and N‐Thioimides with Ruppert‐Prakash reagent (TMS‐CF3) is described. The reaction proceeds at room temperature and only requires NaOAc as the mild promoter to prepare a series of trifluoromethyl thioethers in good to excellent yields. Both aryl and alkyl derivates are well trifluoromethylated under transition‐metal‐free reaction conditions. Moreover, the reaction features with scale‐up synthesis and late‐stage modification of bioactive molecule.

中文翻译:


N-硫代邻苯二甲酰亚胺或N-硫代酰亚胺的无过渡金属全氟烷基化得到全氟烷基硫醚



描述了使用 Ruppert-Prakash 试剂 (TMS-CF3) 对容易获得且稳定的 N-硫代邻苯二甲酰亚胺和 N-硫代酰亚胺进行实用且高效的三氟甲基化。该反应在室温下进行,仅需要 NaOAc 作为温和的促进剂,即可以良好至优异的产率制备一系列三氟甲基硫醚。芳基和烷基衍生物在无过渡金属的反应条件下都能很好地三氟甲基化。此外,该反应还具有生物活性分子的放大合成和后期修饰的特点。
更新日期:2024-06-21
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