Functionalized Metalated Cavitands via Imidation and Late-Stage Elaboration

TitleFunctionalized Metalated Cavitands via Imidation and Late-Stage Elaboration
Publication TypeJournal Article
Year of Publication2015
AuthorsZhao, Y, Swager, TM
JournalEuropean Journal of Organic Chemistry
KeywordsCalixarenes, Cavitands, Late-stage functionalization, Supramolecular chemistry

Efficient methods for the preparation of functionalized metallated cavitands are described. Functional groups can be either introduced by an imidation of metal-oxo complexes or by a late-stage elaboration of the imido ligands. By using diversified iminophosphorane (PPh3=NR) reagents, π-conjugated pyrene, redox active ferrocene, and polymerizable norbornene moieties were successfully introduced. Furthermore, the iodo and alkynyl groups on the imido ligands are capable of undergoing efficient Sonogashira cross-coupling and copper-catalyzed azide alkyne cycloaddition reactions, thereby providing facile access to complex architectures containing metallated cavitands.