Palladium-catalyzed aminations of aryl halides with phosphine-functionalized imidazolium ligands
文献类型：期刊论文
| 作者 | Shi, Ji-cheng1,2; Yang, Pengyu2; Tong, Qingsong1; Jia, Li1 |
| 刊名 | dalton transactions
 |
| 出版日期 | 2008 |
| 期号 | 7页码:938-945 |
| 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. |
| WOS标题词 | science & technology ; physical sciences |
| 类目[WOS] | chemistry, inorganic & nuclear |
| 研究领域[WOS] | chemistry |
| 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 |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000252979000014 |
| 公开日期 | 2015-11-17 |
| 源URL | [http://159.226.238.44/handle/321008/140954]  |
| 专题 | 大连化学物理研究所_中国科学院大连化学物理研究所 |
| 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 |
| 推荐引用方式 GB/T 7714 | 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. |
| APA | Shi, Ji-cheng,Yang, Pengyu,Tong, Qingsong,&Jia, Li.(2008).Palladium-catalyzed aminations of aryl halides with phosphine-functionalized imidazolium ligands.dalton transactions(7),938-945. |
| MLA | Shi, Ji-cheng,et al."Palladium-catalyzed aminations of aryl halides with phosphine-functionalized imidazolium ligands".dalton transactions .7(2008):938-945. |
入库方式： OAI收割
来源：大连化学物理研究所
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