N-Heterocyclic carbenes in organofluorine chemistry

•N-Heterocyclic carbenes in organofluorine chemistry.•Enantioselective fluorinations.•Hydrodefluorinations catalyzed by NHC-metal ion complexes.•NHC catalyzed nucleophilic trifluoromethylations and related reactions.

This short review summarizes the recent progress in organofluorinations catalyzed by N-heterocyclic carbene (NHC)-transition metal ion complexes. NHC-metal ion complexes are increasingly used in a variety of organic transformations, and they have opened up new opportunities, especially in the synthesis of organofluorine compounds. New advances in olefin metathesis, trifluoromethylations, Heck and Suzuki coupling, selective hydrodefluorination, and enantioselective synthesis of organofluorine compounds have been achieved through catalysis by NHC and their metal ion complexes. In this review, synthetic methods for various NHC-metal ion complexes and their applications in the synthesis of organofluorine compounds are comprehensively outlined.

Graphical abstractN-heterocyclic carbenes (NHC) and their transition metal ion complexes catalyze a variety of organofluorinations, including olefin metathesis, trifluoromethylations, Heck and Suzuki coupling, hydrodefluorinations, and enantioselective fluorinations. Synthesis of various NHC-metal ion complexes and their applications in the synthesis of organofluorine compounds is comprehensively reviewed.Figure optionsDownload full-size imageDownload as PowerPoint slide