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

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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-alkynylbenzoates. 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.