Kurose Ryo, Nishii Yuji, Miura Masahiro
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
Org Lett. 2021 Mar 19;23(6):2380-2385. doi: 10.1021/acs.orglett.1c00727. Epub 2021 Mar 11.
Herein we report an efficient synthetic method for the electrophilic trifluoromethylthiolation of aromatic compounds. The key is to use triptycenyl sulfide (Trip-SMe) and TfOH to enhance the electrophilicity of SCF fragment through the formation of sulfonium intermediates. This method enables direct installation of an SCF group onto unactivated aromatics at room temperature, adopting a commercially available saccharin-based reagent. Preliminary DFT calculation was carried out to investigate the substitution effect on the catalytic activity.
在此，我们报道了一种用于芳香族化合物亲电三氟甲硫基化的高效合成方法。关键在于使用三蝶烯基硫醚（Trip-SMe）和三氟甲磺酸（TfOH）通过形成锍中间体来增强SCF片段的亲电性。该方法能够在室温下使用市售的基于糖精的试剂将SCF基团直接安装到未活化的芳烃上。进行了初步的密度泛函理论（DFT）计算以研究取代对催化活性的影响。
