Trifluoromethylthiolation/Selenolation and Lactonization of 2-Alkynylbenzoate: The Application of Benzyl Trifluoromethyl Sulfoxide/Selenium Sulfoxides as SCF3/SeCF3 Reagents

The combined use of BnS(O)CF3/BnSe(O)CF3 with Tf2O as SCF3/SeCF3 reagents was implemented to realize an efficient synthesis of biologically interesting 4-(trifluoromethylthio/ trifluoromethylseleno)isocoumarins from 2-alkynylbenzoa tes. The mechanistic pathway was postulated to involve formation of the electrophilic SCF3/SeCF3 species via interrupted Pummerer reactions followed by a concerted trifluoromethylthiolation/selenolation and lactonization process.

Automated summary

In this study, the combined use of BnS(O)CF3/BnSe(O)CF3 with Tf2O was employed to achieve the efficient synthesis of 4-(trifluoromethylthio/ trifluoromethylseleno)isocoumarins from 2-alkynylbenzoates, which is of significance in biological research. The mechanistic pathway was proposed to involve interrupted Pummerer reactions followed by a concerted trifluoromethylthiolation/selenolation and lactonization process.