Direct Trifluoromethylthiolation of Aziridines: Cation-Controlled Diverse Synthesis of Trifluoromethylthiolated Isothiocyanates and Amines

The direct trifluoromethylthiolation of aziridines with AgSCF3 and iodides is reported. The beta-trifluoromethylthiolated isothiocyanates and amines were selectively obtained by the changed cation of iodide. This strategy is tolerant to a wide range of functional groups with good yields and regioselectivities. In addition, the isothiocyanates can be used for further synthetic manipulation, which offered a convenient approach for SCF3-containing compounds.

Automated summary

The direct trifluoromethylthiolation of aziridines with AgSCF3 and iodides is reported. The beta-trifluoromethylthiolated isothiocyanates and amines were selectively obtained by changing the cation of iodide. This strategy shows good tolerance to a wide range of functional groups with high yields and regioselectivities. Moreover, the obtained isothiocyanates can be used for further synthetic manipulations.