Synthesis of 4-(Bromodifluoromethylseleno) Isocoumarins via Selenolation/Lactonization of 2-Alkynylbenzoates Enabled by a Multi-Component Reagents System
Dongxue Yin, Zhijian Wang, Kaiyue Yang, Yuli Sun, Dan Xiao, Xiaotong Wang, Yunfei Du
Abstract
p -CF 3 BnSeCF 2 Br was developed as a bromodifluoromethylselenonating reagent, which was utilized by combining with m CPBA and Tf 2 O for the synthesis of 4-(bromodifluoromethylseleno) isocoumarins via the selenolation/lactonization of 2-alkynylbenzoates. The transformation was postulated to proceed via a multicomponent reagents system-enabled sequence involving the oxidation of p -CF 3 BnSeCF 2 Br by m CPBA into its selenium sulfoxide, activation of the generated sulfoxide by Tf 2 O into the electrophilic p -CF 3 BnSeOCF 2 Br salt, and selenolation/lactonization of 2-alkynylbenzoates by the reactive electrophilic species into 4-(bromodifluoromethylseleno) isocoumarins.