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Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles
Alternative Title氨基酸促进的、CuI催化的芳基卤代物和胺或含氮杂环形成C-N键的反应
Cai Q(蔡倩); Zhang H(张慧); Ma DW(马大为)
2005
Source PublicationJ. Org. Chem.
ISSN0022-3263
Volume70Issue:13Pages:5164-5173
AbstractCuI-catalyzed coupling reaction of electron-deficient aryl iodides with aliphatic primary amines occurs at 40 degrees C under the promotion of N-methylglycine. Using L-proline as the promoter, coupling reaction of aryl iodides or aryl bromides with aliphatic primary amines, aliphatic cyclic secondary amines, or electron-rich primary arylamines proceeds at 60-90 degrees C; an intramolecular coupling reaction between aryl chloride and primary amine moieties gives indoline at 70 degrees C; coupling reaction of aryl iodides with indole, pyrrole, carbazole, imidazole, or pyrazole can be carried out at 75-90 degrees C; and coupling reaction of electron-deficient aryl bromides with imidazole or pyrazole occurs at 60-90 degrees C to provide the corresponding N-aryl products in good to excellent yields. In addition, N,N-dimethylglycine promotes the coupling reaction of electron-rich aryl bromides with imidazole or pyrazole to afford the corresponding N-aryl imidazoles or pyrazoles at 110 degrees C. The possible action of amino acids in these coupling reactions is discussed.
Subject Area金属有机化学
Department上海有机所; 复旦大学
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Indexed BySCI
Language英语
WOS IDWOS:000229982900034
Citation statistics
Cited Times:612[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/15491
Collection生命有机化学国家重点实验室
Corresponding AuthorMa DW(马大为)
Recommended Citation
GB/T 7714
Cai Q,Zhang H,Ma DW. Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles[J]. J. Org. Chem.,2005,70(13):5164-5173.
APA 蔡倩,张慧,&马大为.(2005).Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles.J. Org. Chem.,70(13),5164-5173.
MLA 蔡倩,et al."Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles".J. Org. Chem. 70.13(2005):5164-5173.
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