Imidazolium-Based and Related Multidentate Halogen-Bond Donors: Synthesis, Characterization and Application in Substitution and Diels-Alder Reactions

This work focused on the synthesis, modification, and characterization of multidentate halogen-bond donors based on imidazolium and related scaffolds. The applicability of these halogen-bond donors, both neutral and cationic, as activators in organic synthesis was tested in benchmark reactions. The impact of temperature, solvent and counteranions on the coordination strength of charged halogen-bond donors was examined. Proofs of principle for the applicability of halogen-bond donors in both substitution and Diels-Alder reactions were achieved and data aiding in the rational design of such activators was gathered.