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Functionalized Metalated Cavitands via Imidation and Late‐Stage Elaboration
Author(s) -
Zhao Yanchuan,
Swager Timothy M.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500714
Subject(s) - chemistry , sonogashira coupling , cycloaddition , combinatorial chemistry , reagent , alkyne , synthon , conjugated system , azide , ferrocene , organic chemistry , palladium , catalysis , electrode , electrochemistry , polymer
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 (PPh 3 =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.