Metal-Free Direct Trifluoromethylthiolation of Aromatic Compounds Using Triptycenyl Sulfide Catalyst

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 SCF3 fragment through the formation of sulfonium intermediates.
This method enables direct installation of an SCF3 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.

本文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。该方法的核心在于采用三蝶烯基硫醚（Trip-SMe）与三氟甲磺酸（TfOH），通过形成锍中间体以增强SCF₃（三氟甲硫基）片段的亲电性。本方法借助市售糖精类试剂，可在室温条件下将SCF₃基团直接安装至未活化芳烃上。我们开展了初步的密度泛函理论（DFT, Density Functional Theory）计算，以探究取代效应对催化活性的影响。