Synthesis of 4-(pentafluorosulfanyl)benzenediazonium tetrafluoroborate and Analogs
    7.
    发明申请
    Synthesis of 4-(pentafluorosulfanyl)benzenediazonium tetrafluoroborate and Analogs 有权
    4-(五氟硫烷基)苯并氮鎓四氟硼酸盐的合成及类似物

    公开(公告)号:US20160096852A1

    公开(公告)日:2016-04-07

    申请号:US14966769

    申请日:2015-12-11

    Inventor: Kenneth K. Laali

    Abstract: 4-(pentafluorosulfanyl)benzenediazonium tetrafluoroborate salt was synthesized and isolated. The pentafluorosulfanyl salt was examined in a wide assortment of reactions to form novel SF5-bearing alkenes, alkynes, and biaryl derivatives using Heck-Matsuda, Sonogashira, and Suzuki coupling protocols. Dediazoniation of the salt furnished the corresponding p-SF5—C6H4X,C6H4OS(O)(CF3)═NSO2CF3, and p-SF5—C6H4—NTf2 derivatives. The azide derivative p-SF5—C6H4N3 entered into click chemistry with phenylacetylenes to furnish the corresponding triazoles. Various SF5-bearing alkenes were synthesized by coupling reactions using a metal catalyst. Fluorodediazoniation selectively furnished the fluoro derivative p-SF5—C6H4F. Homolytic dediazoniation gave the unsymmetrical biaryls, thus demonstrating the broad utility of pentafluorosulfanyl diazonium salts as building blocks of SF5-aromatics that are in high demand in many branches of chemistry including biomedicine and materials chemistry.

    Abstract translation: 合成并分离出4-(五氟硫烷基)苯二氮鎓四氟硼酸盐。 使用Heck-Matsuda,Sonogashira和Suzuki偶联方案,在各种各样的反应中检查五氟硫烷基盐以形成新的含SF5的烯烃,炔烃和联芳基衍生物。 盐的淡化提供相应的对应的SF-C6H4X,C6H4OS(O)(CF3)= NO2O2CF3和p-SF5-C6H4-NTf2衍生物。 叠氮衍生物p-SF5-C6H4N3与苯乙炔进行点击化学反应,得到相应的三唑。 通过使用金属催化剂的偶联反应合成了各种含SF5的烯烃。 氟代氮化选择性提供氟衍生物p-SF5-C6H4F。 均相脱氮化得到不对称的联芳基,从而证明五氟硫烷基重氮盐作为SF5芳族化合物的结构单元的广泛用途,其在包括生物医学和材料化学在内的许多化学分支中具有高需求。

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