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Palladium-catalyzed aminations of aryl halides with phosphine-functionalized imidazolium ligands
Shi, Ji-cheng1,2; Yang, Pengyu2; Tong, Qingsong1; Jia, Li1
Source PublicationDALTON TRANSACTIONS
2008
DOI10.1039/b714892e
Issue7Pages:938-945
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Inorganic & Nuclear
WOS Research AreaChemistry
WOS KeywordCROSS-COUPLING REACTIONS ; N-HETEROCYCLIC CARBENES ; BUCHWALD-HARTWIG REACTIONS ; SUZUKI-MIYAURA ; ROOM-TEMPERATURE ; HIGHLY EFFICIENT ; OLEFIN METATHESIS ; RHODIUM COMPLEXES ; CHLORIDES ; BROMIDES
AbstractA 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.
Language英语
WOS IDWOS:000252979000014
Citation statistics
Cited Times:18[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/140954
Collection中国科学院大连化学物理研究所
Affiliation1.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
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.
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