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题名: Palladium-catalyzed aminations of aryl halides with phosphine-functionalized imidazolium ligands
作者: Shi, Ji-cheng1, 2;  Yang, Pengyu2;  Tong, Qingsong1;  Jia, Li1
刊名: DALTON TRANSACTIONS
发表日期: 2008
DOI: 10.1039/b714892e
期: 7, 页:938-945
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Inorganic & Nuclear
研究领域[WOS]: Chemistry
英文摘要: A series of 1-(2-diphenylphosphinoferrocenyl)ethyl-3-substituted imidazolium iodides [3-substituent = methyl (1a); isopropyl (1b); tert-butyl (1c); 1-adenosyl (1d); cyclohexyl (1e); 2,6-dimethylphenyl (1f); 2,4,6-trimethylphenyl (1g); 2,6-diisopropylphenyl (1h)] have been prepared and evaluated as ligands in the palladium-catalyzed aminations of aryl halides with various amines. The scope of the coupling process was carried out for various aryl bromides and chlorides with the catalysts generated in situ from a mixture of Pd(OAc)(2) and 1 in the presence of a base. (NaOBu)-Bu-t was found the choice of base in combination with dioxane, toluene, or DME as solvent, although NaOH or Cs2CO3 promoted the coupling of 4-bromotoluene with morpholine in moderate conversion. The steric hindrance from the 3-substituent of imidazolium in the hybrid-bidentate chelating system was found to be only beneficial to the substrates without ortho-substituents. The more sterically hindered 1d or 1h promoted the coupling of bromobenzene with morpholine in nearly quantitative conversion with 0.2 mol% of palladium loading in the presence of (NaOBu)-Bu-t at 110 degrees C, and 94% of conversion was afforded with the less sterical demanding 1a for a longer time. However, for the substrates with ortho-substituents, higher conversions were achieved with 1a. The Pd(OAc)(2)/1d catalytic system was also active for deactivated aryl chloride, and 71% isolated yield for the desired product was realized for coupling of 4-chloroanisole with morpholine at 2 mol% of catalyst loading. The developed catalyst system has been applied successfully to the synthesis of a key building block for a type of functional polymers.
关键词[WOS]: CROSS-COUPLING REACTIONS ;  N-HETEROCYCLIC CARBENES ;  BUCHWALD-HARTWIG REACTIONS ;  SUZUKI-MIYAURA ;  ROOM-TEMPERATURE ;  HIGHLY EFFICIENT ;  OLEFIN METATHESIS ;  RHODIUM COMPLEXES ;  CHLORIDES ;  BROMIDES
语种: 英语
WOS记录号: WOS:000252979000014
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/140954
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Fujian Normal Univ, Coll Med & Mat Sci, Fuzhou 350007, Peoples R China
2.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Liaoning, Peoples R China

Recommended Citation:
Shi, Ji-cheng,Yang, Pengyu,Tong, Qingsong,et al. Palladium-catalyzed aminations of aryl halides with phosphine-functionalized imidazolium ligands[J]. DALTON TRANSACTIONS,2008(7):938-945.
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