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首页> 外文期刊>Chemistry: A European journal >Large yet Flexible N-Heterocyclic Carbene Ligands for Palladium Catalysis
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Large yet Flexible N-Heterocyclic Carbene Ligands for Palladium Catalysis

机译：用于钯催化的大而灵活的N杂环碳配体

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摘要

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-tri-methylphenyl)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.
机译：已经从廉价且容易获得的2-硝基-间二甲苯开发了一种新的，可扩展的八步合成新的N-杂环卡宾（NHC）的方法。该方法允许制备一类新的NHC，其被称为ITent（“帐篷”为“触角”），其中著名的IMes（N，N'-双（2,4,6-三甲基苯基）咪唑- 2-亚烷基），IPr（N，N'-双（2,6-二（2-丙基）苯基）咪唑-2-亚烷基）和IPent（N，N'-双（2,6-二（3-戊基）苯基）咪唑-2-亚基NHC是最简单且已知的同类物。该合成路线已成功用于ITent家族的三个成员的制备：IPent（N，N'-双（2，6-二（3-戊基）苯基）咪唑-2-亚基），IHept（N，N '-双（2,6-二（4-庚基）苯基）咪唑-2-亚烷基）和INon（N，N'-双（2,6-二（5-壬基）苯基）咪唑-2-亚烷基） 。通过制备镍和钯配合物，研究了每种NHC的电子和空间特性。最后，研究了这些新的ITent配体在Pd催化的Suzuki-Miyaura和Buchwald-Hartwig交叉偶联中的作用。

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