Synthesis of Aryl Perfluorocyclopropyl Ethers via [2 + 1] Cyclopropanation Using TMSCF2Br Reagent

Aryl perfluorocyclopropyl ethers have been synthesized for the first time by [2 + 1] cyclopropanation between aryl trifluorovinyl ethers and a commercially available TMSCF2Br reagent. This cycloaddition reaction between two fluorine-containing reactants proceeds smoothly in toluene at 120 °C in the presence of a catalytic amount of n-Bu4NBr, and the reaction tolerates a variety of functional groups. A wide range of aryl trifluorovinyl ethers, easily accessible from phenols, were successfully transformed to aryl perfluorocyclopropyl ethers.