Wiesenfeldt Mario P, Knecht Tobias, Schlepphorst Christoph, Glorius Frank
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany.
Angew Chem Int Ed Engl. 2018 Jul 2;57(27):8297-8300. doi: 10.1002/anie.201804124. Epub 2018 Jun 21.
We report a method to convert readily available silylated arenes into silylated saturated carbo- and heterocycles by arene hydrogenation. The scope includes alkoxy- and halosilyl substituents. Silyl groups can be derivatized into a plethora of functionalities and find application in organic synthesis, materials science, and pharmaceutical, agrochemical, and fragrance research. However, silylated saturated (hetero- ) cycles are difficult to access with current technologies. The yield of the hydrogenation depends on the amount of the silica gel additive. This silica effect also enables a significant improvement of a previously disclosed method for the hydrogenation of highly fluorinated arenes (e.g., to all-cis-C H F ).
我们报道了一种通过芳烃氢化将容易获得的甲硅烷基化芳烃转化为甲硅烷基化饱和碳环和杂环的方法。其适用范围包括烷氧基和卤代甲硅烷基取代基。甲硅烷基可衍生为多种官能团，并在有机合成、材料科学以及制药、农用化学品和香料研究中得到应用。然而，目前的技术难以获得甲硅烷基化饱和（杂）环。氢化产率取决于硅胶添加剂的用量。这种硅胶效应还能显著改进先前公开的用于高度氟化芳烃氢化的方法（例如，生成全顺式C₆H₆F₆）。
