3-Acetylcoumarin as a Practical Ligand for Copper-Catalyzed C-N Coupling Reactions at Room Temperature

被引：21

作者：

Tao, Chuan-Zhou ^{[1
,2
]}

Liu, Wei-Wei ^{[1
]}

Sun, Ji-You ^{[1
]}

Cao, Zhi-Ling ^{[1
]}

Li, Hui ^{[1
]}

Zhang, Ying-Fen ^{[1
]}

机构：

[1] Huaihai Inst Technol, Dept Chem Engn, Lianyungang 222005, Peoples R China

[2] Huaihai Inst Technol, Jiangsu Key Lab Marine Biotechnol, Lianyungang 222005, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2010年 / 08期

关键词：

copper; catalysis; cross-coupling; 3-acetylcoumarin; room temperature; LONG-LIVED CATALYSTS; ARYL IODIDES; BOND FORMATION; CONTAINING HETEROCYCLES; NITROGEN NUCLEOPHILES; HETEROARYL HALIDES; GOLDBERG REACTIONS; AMINATION; ARYLATION; EFFICIENT;

D O I：

10.1055/s-0029-1218661

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of coumarin-based ligands was examined in copper-catalyzed C-N cross-coupling reactions. It was found that 3-acetylcoumarin constituted a new, practical ligand for the copper-catalyzed N-arylation of aliphatic amines and imidazole with aryl iodides at room temperature. Aryl bromides could also be aminated efficiently at 80 degrees C. This readily available catalyst system, namely copper(I) iodide and 3-acetylcoumarin, provides a mild and practical method for the synthesis of aromatic amines.

引用

页码：1280 / 1284

页数：5

共 52 条

[1] Orthogonal Pd- and Cu-based catalyst systems for C- and N-arylation of oxindoles
Altman, Ryan A.
Hyde, Alan M.
Huang, Xiaohua
Buchwald, Stephen L.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) : 9613 - 9620
[2] Copper-catalyzed N-arylation of imidazoles and benzimidazoles
Altman, Ryan A.
Koval, Erica D.
Buchwald, Stephen L.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) : 6190 - 6199
[3] 4,7-Dimethoxy-1,10-phenanthroline:: An excellent ligand for the Cu-catalyzed N-arylation of imidazoles
Altman, Ryan A.
Buchwald, Stephen L.
[J]. ORGANIC LETTERS, 2006, 8 (13) : 2779 - 2782
[4] Copper in cross-coupling reactions - The post-Ullmann chemistry
Beletskaya, IP
Cheprakov, AV
[J]. COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) : 2337 - 2364
[5] BERKEL SSV, 2009, CHEM COMMUN, P4272
[6] Mild Conditions for Pd-Catalyzed Carboamination of N-Protected Hex-4-enylamines and 1-, 3-, and 4-Substituted Pent-4-enylamines. Scope, Limitations, and Mechanism of Pyrrolidine Formation
Bertrand, Myra Beaudoin
Neukom, Joshua D.
Wolfe, John P.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) : 8851 - 8860
[7] Efficient Pd-catalyzed amination of heteroaryl halides
Charles, MD
Schultz, P
Buchwald, SL
[J]. ORGANIC LETTERS, 2005, 7 (18) : 3965 - 3968
[8] Ligand-free copper-catalyzed N-arylation of nitrogen nucleophiles
Correa, Arkaitz
Bolm, Carsten
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (17-18) : 2673 - 2676
[9] Copper-catalyzed cross-coupling of sulfonamides with aryl iodides and bromides facilitated by amino acid ligands
Deng, W
Liu, L
Zhang, C
Liu, M
Guo, QX
[J]. TETRAHEDRON LETTERS, 2005, 46 (43) : 7295 - 7298
[10] Amino acid-mediated Goldberg reactions between amides and aryl iodides
Deng, W
Wang, YF
Zou, W
Liu, L
Guo, QX
[J]. TETRAHEDRON LETTERS, 2004, 45 (11) : 2311 - 2315

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