Practical copper-catalyzed N-arylation of nitrogen heterocycles with aryl halides under ligand and additive free conditions

被引：74

作者：

Chang, Joyce Wei Wei ^{[1
]}

Xu, Xiuhui ^{[1
]}

Chan, Philip Wai Hong ^{[1
]}

机构：

[1] Nanyang Technol Univ, Coll Sci, Sch Math & Phys Sci, Div Chem & Biol Chem, Singapore, Singapore

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 02期

关键词：

D O I：

10.1016/j.tetlet.2006.11.050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-arylation of a wide variety of nitrogen heterocycles with aryl iodides catalyzed by copper iodide under mild ligand and additive free conditions ((Bu4NBr)-Bu-11, PhMe, NaOH, reflux, 22 h) was accomplished in good to excellent yields (up to 95%) and substrate conversions (up to 99%). (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：245 / 248

页数：4

共 46 条

[1] Synthetic approaches to sterically hindered N-arylimidazoles through copper-catalyzed coupling reactions [J].

Alcalde, E ;

Dinarès, I ;

Rodríguez, S ;

de Miguel, CG .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (08) :1637-1643

[2] 4,7-Dimethoxy-1,10-phenanthroline:: An excellent ligand for the Cu-catalyzed N-arylation of imidazoles [J].

Altman, Ryan A. ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2006, 8 (13) :2779-2782

[3] The copper-catalyzed N-arylation of indoles [J].

Antilla, JC ;

Klapars, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11684-11688

[4] Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles [J].

Antilla, JC ;

Baskin, JM ;

Barder, TE ;

Buchwald, SL .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5578-5587

[5] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[6] The [Cu(OH)•TMEDA]2Cl2-catalyzed coupling of arylboronic acids with imidazoles in water [J].

Collman, JP ;

Zhong, M ;

Zeng, L ;

Costanzo, S .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1528-1531

[7] An efficient diamine copper complex-catalyzed coupling of arylboronic acids with imidazoles [J].

Collman, JP ;

Zhong, M .

ORGANIC LETTERS, 2000, 2 (09) :1233-1236

[8]

Craig P. N., 1991, COMPREHENSIVE MED CH, V8

[9] Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides [J].

Cristau, HJ ;

Cellier, PP ;

Spindler, JF ;

Taillefer, M .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (22) :5607-5622

[10] Mild conditions for copper-catalysed N-arylation of pyrazoles [J].

Cristau, HJ ;

Cellier, PP ;

Spindler, JF ;

Taillefer, M .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (04) :695-709

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