Fluoroalkylated hypervalent sulfur fluorides: radical addition of arylchlorotetrafluoro-λ6-sulfanes to tetrafluoroethylene,Chemical Science

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Fluoroalkylated hypervalent sulfur fluorides: radical addition of arylchlorotetrafluoro-λ6-sulfanes to tetrafluoroethylene
Chemical Science ( IF 7.6 ) Pub Date : 2023-10-19 , DOI: 10.1039/d3sc04837c
Eisuke Yasuo ₁ , Kohsuke Aikawa ₁ , Kyoko Nozaki ₂ , Takashi Okazoe _{1,

3}

Affiliation

Fluorinated groups are essential hydrophobic groups in drug design. Combining a carbon-free tetrafluoro-λ⁶-sulfanyl (SF₄) group with a polyfluoroalkyl group (R_F) provides SF₄R_F groups, exhibiting high hydrophobicity with a short carbon chain. In this study, various aryltetrafluoro(polyfluoroalkyl)-λ⁶-sulfanes (ArSF₄R_F) were synthesized through the radical addition of arylchlorotetrafluoro-λ⁶-sulfanes (ArSF₄Cl) to tetrafluoroethylene. In addition, quantification of hydrophobic constants (π_Ph) indicated that the SF₄ group is considerably more hydrophobic than a difluoromethylene (CF₂) group. Further transformation reactions revealed the stabilities and reactivities of these novel fluorinated groups. The high hydrophobicity and synthetic utility of the SF₄R_F group lead to the potential applications of the SF₄R_F group in the pharmaceutical field.

中文翻译：

氟烷基化高价氟硫：芳基氯四氟-λ6-sulfane 到四氟乙烯中的自由基加成反应

氟化基团是药物设计中必不可少的疏水基团。将无碳四氟-λ⁶-磺酰（SF₄）基团与多氟烷基（R_F）结合得到 SF₄R_F 基团，表现出高疏水性和短碳链。本研究通过向四氟乙烯加成芳基氯四氟-λ⁶-磺烷（ArSF₄Cl）合成了各种芳基四氟（多氟烷基）-λ⁶-磺烷（ArSF₄R_F）。此外，疏水常数（π_Ph）的定量表明，SF₄ 基团的疏水性比二氟亚甲基（CF₂）基团强得多。进一步的转化反应揭示了这些新型氟化基团的稳定性和反应性。SF₄R_F 基团的高疏水性和合成效用使 SF₄R_F 基团在制药领域具有潜在的应用。

更新日期：2023-10-19

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