Deoxyfluorination of Electron-Deficient Phenols

In this study, wereport a facile synthesis of 2-chloro-1,3-bis-(2,6-diisopropylphenyl)-imidazoliumsalts in aqueous media under ambient conditions using hypochloriteas a chlorinating agent. In addition, an air-stable and moisture-insensitivedeoxyfluorination reagent based on poly-[hydrogen fluoride] salt ispresented, which is capable of converting electron-deficient phenolsor aryl silyl ethers into the corresponding aryl fluorides in thepresence of DBU as a base, with good to excellent yields and hightolerance to functional groups.

Automated summary

In this study, a simple method for the synthesis of 2-chloro-1,3-bis-(2,6-diisopropylphenyl)-imidazolium salts in aqueous media using hypochlorite as a chlorinating agent was reported. Additionally, an air-stable and moisture-insensitive deoxyfluorination reagent based on poly-[hydrogen fluoride] salt was presented, which can convert electron-deficient phenols or aryl silyl ethers into corresponding aryl fluorides in the presence of DBU as a base, with high yields and good tolerance to functional groups.