Trifluoromethylthiolation/Selenolation and Lactonization of 2-Alkynylbenzoate: The Application of Benzyl Trifluoromethyl Sulfoxide/Selenium Sulfoxides as SCF<sub>3</sub>/SeCF<sub>3</sub> Reagents
Haofeng Shi, Xingzong Wang, Xiaoxian Li, Beibei Zhang, Xuemin Li, Jingran Zhang, Jingyue Yang, Yunfei Du
Abstract
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.
Topics & Concepts
ChemistryReagentSulfoxideElectrophileTrifluoromethylSeleniumPummerer rearrangementCombinatorial chemistryOrganic chemistryStereochemistryCatalysisAcetic anhydrideAlkylFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesInorganic Fluorides and Related Compounds