期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 19, 期 51, 页码 17358-17368出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201302471
关键词
bulky; catalysis; flexible; N-heterocyclic carbene; palladium; tentacular
资金
- EC
- Royal Society
A straightforward and scalable eight-step synthesis of new N-heterocyclic carbenes (NHCs) has been developed from inexpensive and readily available 2-nitro-m-xylene. This process allows for the preparation of a novel class of NHCs coined ITent (Tent for tentacular) of which the well-known IMes (N,N-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene), IPr (N,N-bis(2,6-di(2-propyl)phenyl)imidazol-2-ylidene) and IPent (N,N-bis(2,6-di(3-pentyl)phenyl)imidazol-2-ylidene) NHCs are the simplest and already known congeners. The synthetic route was successfully used for the preparation of three members of the ITent family: IPent (N,N-bis(2,6-di(3-pentyl)phenyl)imidazol-2-ylidene), IHept (N,N-bis(2,6-di(4-heptyl)phenyl)imidazol-2-ylidene) and INon (N,N-bis(2,6-di(5-nonyl)phenyl)imidazol-2-ylidene). The electronic and steric properties of each NHC were studied through the preparation of both nickel and palladium complexes. Finally the effect of these new ITent ligands in Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-couplings was investigated.
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