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<p>Pentafluorosulfanyl group has been long considered a potential (bio)isostere for <i>tert</i>-butyl and trifluoromethyl groups, yet limitations in methodologies have constrained access to it. To bridge this gap, we have developed a general pentafluorosulfanylation platform that employs bench-stable solid reagents to generate SF<sub>5</sub> radicals via a decarboxylation and <i>β</i>-scission sequence. This strategy enables a variety of operationally simple transformations, expanding the accessibility of SF<sub>5</sub>-containing molecules. Notably, this reagent design is also adaptable to other persulfuranyl groups, such as trifluoromethyl tetrafluorosulfanyl and aryl tetrafluorosulfanyl groups. Taken together, generating a collection of these stable reagents and practitioner-friendly chemical methodologies enables the synthesis of challenging and biologically relevant sulfur(VI) chemical entities in an expedient manner.</p>

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Bench-stable reagents for modular access to persulfuranyl scaffolds

  • 期刊论文

  • 出版模式：

    开放获取

  • 发表日期：

    2025年11月19日

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  • Renzhe Li,
  • Chang Liu,
  • Chao Hu,
  • Jet Tsien,
  • Michael Hayes,
  • Si-Jie Chen,
  • Yuzuru Kanda,
  • Rohan R. Merchant,
  • Bryan S. Matsuura,
  • Tian Qin

摘要

Pentafluorosulfanyl group has been long considered a potential (bio)isostere for tert-butyl and trifluoromethyl groups, yet limitations in methodologies have constrained access to it. To bridge this gap, we have developed a general pentafluorosulfanylation platform that employs bench-stable solid reagents to generate SF5 radicals via a decarboxylation and β-scission sequence. This strategy enables a variety of operationally simple transformations, expanding the accessibility of SF5-containing molecules. Notably, this reagent design is also adaptable to other persulfuranyl groups, such as trifluoromethyl tetrafluorosulfanyl and aryl tetrafluorosulfanyl groups. Taken together, generating a collection of these stable reagents and practitioner-friendly chemical methodologies enables the synthesis of challenging and biologically relevant sulfur(VI) chemical entities in an expedient manner.