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Straightforward Pentafluorosulfanylation for Molecular Design
ChemRxiv Pub Date : 2023-04-21 , DOI: 10.26434/chemrxiv-2023-jzn11 Tim Gatzenmeier 1 , Yue Liu 1 , Misato Akamatsu 1 , Takashi Okazoe 2 , Kyoko Nozaki 1
ChemRxiv Pub Date : 2023-04-21 , DOI: 10.26434/chemrxiv-2023-jzn11 Tim Gatzenmeier 1 , Yue Liu 1 , Misato Akamatsu 1 , Takashi Okazoe 2 , Kyoko Nozaki 1
Affiliation
Pentafluorosulfanylation is a powerful boost of molecular properties for many applications. In order to leverage its full potential, a direct and high-yielding synthetic strategy is in great demand. We report here how the discovery of a direct pentafluorosulfanylation of thiolated arenes led to a generalized synthetic approach toward aryl– and heteroaryl pentafluorosulfanyl (SF5) compounds from various common building blocks. The combination of onium halides with silver(II) fluoride (AgF2) provided drastically enhanced oxidative fluorination conditions that enabled the single-step conversion of various thiophenol derivatives to SF5-compounds in high yields and broad scope. The particularly high reaction rate is accounted to an onium fluoroargentate(II)-mediated fluorination mechanism. The recycling potential of inorganic silver byproducts furthermore offers an avenue into industrial-scale production.
中文翻译:
用于分子设计的简单五氟磺基化
五氟硫烷基化可有效提升许多应用的分子特性。为了充分发挥其潜力,迫切需要一种直接且高产的合成策略。我们在此报告硫醇化芳烃的直接五氟硫烷基化的发现如何导致从各种常见结构单元中合成芳基和杂芳基五氟硫基 (SF5) 化合物的通用合成方法。卤化鎓与氟化银 (AgF2) 的组合提供了显着增强的氧化氟化条件,使各种苯硫酚衍生物能够以高产率和广泛的范围单步转化为 SF5 化合物。特别高的反应速率归因于氟银酸鎓 (II) 介导的氟化机制。
更新日期:2023-04-21
中文翻译:
用于分子设计的简单五氟磺基化
五氟硫烷基化可有效提升许多应用的分子特性。为了充分发挥其潜力,迫切需要一种直接且高产的合成策略。我们在此报告硫醇化芳烃的直接五氟硫烷基化的发现如何导致从各种常见结构单元中合成芳基和杂芳基五氟硫基 (SF5) 化合物的通用合成方法。卤化鎓与氟化银 (AgF2) 的组合提供了显着增强的氧化氟化条件,使各种苯硫酚衍生物能够以高产率和广泛的范围单步转化为 SF5 化合物。特别高的反应速率归因于氟银酸鎓 (II) 介导的氟化机制。