Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles

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	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.
	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.