卡宾
IMes公司
钯
化学
催化作用
位阻效应
药物化学
镍
硝基
组合化学
配体(生物化学)
立体化学
有机化学
烷基
生物化学
受体
作者
Sébastien Meiries,Gaëtan Le Duc,Anthony Chartoire,Alba Collado,Klaus Speck,Kasun S. Athukorala Arachchige,Alexandra M. Z. Slawin,Steven P. Nolan
标识
DOI:10.1002/chem.201302471
摘要
Abstract 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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