Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, Poznań 61-704, Poland.
Laboratory of Homogeneous Catalysis and Molecular Design at the Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, Łodź PL-90-363, Poland.
J Am Chem Soc. 2022 Jun 15;144(23):10438-10445. doi: 10.1021/jacs.2c02611. Epub 2022 Jun 2.
Increased interest in the trifluoromethoxy group in organic synthesis and medicinal chemistry has induced a demand for new, selective, general, and faster methods applicable to natural products and highly functionalized compounds at a later stage of hit-to-lead campaigns. Applying pyrylium tetrafluoroborate, we have developed a mechanochemical protocol to selectively substitute the aromatic amino group with the OCF functionality. The scope of our method includes 31 examples of ring-substituted anilines, including amides and sulfonamides. Expected SAr products were obtained in excellent yields. The presented concise method opens a pathway to new chemical spaces for the pharmaceutical industry.
在有机合成和药物化学中，三氟甲氧基基团的应用日益受到关注，这促使人们需要新的、选择性的、通用的、更快的方法，以适用于天然产物和在先导化合物优化阶段的高度功能化化合物。我们应用吡喃四氟硼酸盐，开发了一种机械化学方法，可选择性地将芳香族氨基基团用 OCF 官能团取代。我们的方法包括 31 个取代芳基苯胺的例子，包括酰胺和磺胺。预期的 SAr 产物以优异的收率获得。所提出的简洁方法为制药行业开辟了通往新化学领域的途径。
