Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr, Germany.
Org Lett. 2020 Jun 19;22(12):4593-4596. doi: 10.1021/acs.orglett.0c00982. Epub 2020 Apr 7.
Aryl sulfinates are precursors to a diverse number of sulfonyl-derived arenes, which are common motifs in pharmaceuticals and agrochemicals. Here, we report a site-selective two-step C-H sulfination sequence via aryl sulfonium salts to access aryl sulfonamides. Combined with site-selective aromatic thianthrenation, an operationally simple one-pot palladium-catalyzed protocol introduces the sulfonyl group using sodium hydroxymethylsulfinate (Rongalite) as a source of SO. The hydroxymethyl sulfone intermediate generated from the catalytic process can be employed as a synthetic handle to deliver a variety of sulfonyl-containing compounds.
芳基磺酸盐是多种磺酰基衍生芳基的前体，它们是药物和农用化学品中的常见结构单元。在这里，我们报告了通过芳基锍盐进行的选择性两步 C-H 磺化反应序列，以获得芳基磺酰胺。结合选择性芳基噻蒽化反应，使用亚硫酸氢甲酯钠（罗乃尔）作为 SO 的来源，采用操作简单的一锅钯催化法，可以引入磺酰基。催化过程中生成的羟甲基砜中间体可用作合成手段，以提供各种含磺酰基的化合物。
