Ring opening of sugar-derived epoxides by TBAF/KHF2: An attractive alternative for the introduction of fluorine into the carbohydrate scaffold

A stable and commercially available reagent mixture, composed of tetrabutylammonium bifluoride/potassium bifluoride (TBAF/KHF2), was found to be effective for the nucleophilic fluorine ring-opening of sugar-derived epoxides. Different sugar-derived epoxide precursors, including 1-thioglycosides can be ring-opened to afford fluorinated carbohydrate products in high yields and short reaction times.