Electroactive Imidazolium Ionic Liquids in Organic Synthesis

The renewed interest in electrochemistry in organic synthesis has provided new opportunities for the development of novel and efficient chemical transformations. In this context, ionic liquids (ILs) have emerged as privileged media due to their peculiar properties, including negligible vapor pressure, high coordination ability and thermal stability, and a wide electrochemical window. Among them, imidazolium-based ILs are of high interest since they can be used not only as solvent/supporting electrolytes but also as electrochemical precursors for reactive species. This Account discusses recent advances in the use of electroactive imidazolium-based ILs in organic synthesis, focusing on the electrogeneration of Lewis acids (LAs) and N-heterocyclic carbenes (NHCs). Key strategies are discussed, with a critical discussion of the electrochemical behavior and setups as well as their impact on reaction design and selectivity as compared with conventional synthetic methods. Overall, this work aims to provide a comprehensive overview of the emerging possibilities that the combination of electrochemistry and ionic liquids provides and to outline the possible future perspectives for their applications in organic synthesis.