Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles | |
Cai Q(蔡倩) ; Zhang H(张慧) ; Ma DW(马大为) | |
刊名 | J. Org. Chem.
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2005 | |
卷号 | 70期号:13页码:5164-5173 |
ISSN号 | 0022-3263 |
其他题名 | 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 |
通讯作者 | 马大为 |
英文摘要 | CuI-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. |
学科主题 | 金属有机化学 |
收录类别 | SCI |
原文出处 | http://dx.doi.org/10.1021/jo0504464 |
语种 | 英语 |
WOS记录号 | WOS:000229982900034 |
公开日期 | 2013-02-19 |
内容类型 | 期刊论文 |
源URL | [http://202.127.28.38/handle/331003/15491] ![]() |
专题 | 上海有机化学研究所_生命有机化学国家重点实验室 |
推荐引用方式 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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