Development of Shelf-Stable Reagents for Fluoro-Functionalization Reactions

It is highly probable that the first impression that organic chemists would have of fluorine, F, is that it is dangerous. Elemental fluorine, F-2, is a gas that reacts with all elements quickly and violently. The oxidation power of F-2 is extraordinarily strong and even the noble gases such as Kr and Xe react with F-2 forming the corresponding fluorides. Fortunately, the receptiveness to fluorine chemistry by synthetic chemists has gradually changed in the late 20th century with the development of shelf-stable reagents for fluorination and trifluoromethylation reactions. In this account, I introduce our recent contributions to the development of shelf-stable reagents for the synthesis of organofluorine compounds. Electrophilic reagents for fluorination, mono-, di-, and trifluoromethylation, and trifluoromethylthiolation are discussed. Nucleophilic reagents for monofluoromethylation are also described including enantioselective reactions.