Development of shelf-stable reagents for fluoro-functionalization reactions

Abstract

It is highly probable that the first impression that organic chemists would have of fluorine, F, is that it is "dangerous". Elemental fluorine, F2, is a gas that reacts with all elements quickly and violently. The oxidation power of F2 is extraordinarily strong and even the noble gases such as Kr and Xe react with F2 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.