Functionalized Metalated Cavitands via Imidation and Late-Stage Elaboration

• Main Authors: Zhao, Yanchuan (Contributor), Swager, Timothy M (Contributor)
• Other Authors: Massachusetts Institute of Technology. Department of Chemistry (Contributor)
• Format: Article
• Language: English
• Published: Wiley Blackwell, 2017-07-03T13:02:35Z.
• Subjects: Article
• Online Access: Get fulltext

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.
National Institutes of Health (U.S.) (GM095843)