Selective copper catalysed aromatic N-arylation in water

被引:65
作者
Engel-Andreasen, Jens [1 ]
Shimpukade, Bharat [1 ]
Ulven, Trond [1 ]
机构
[1] Univ So Denmark, Dept Phys Chem & Pharm, DK-5230 Odense M, Denmark
关键词
ARYL HALIDES; COUPLING REACTIONS; CROSS-COUPLINGS; MILD CONDITIONS; C-N; IMIDAZOLES; LIGANDS; LOADINGS; NITROGEN; SYSTEM;
D O I
10.1039/c2gc36589h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
4,7-Dipyrrolidinyl-1,10-phenanthroline (DPPhen) was identified as an efficient ligand for copper catalysed selective aromatic N-arylation in water. N-Arylation of indoles, imidazoles and purines proceeds with moderate to excellent yields and complete selectivity over aliphatic amines. Aqueous medium and the possibility for low metal and ligand loadings give the process a benign environmental profile.
引用
收藏
页码:336 / 340
页数:5
相关论文
共 32 条
[1]   An improved cu-based catalyst system for the reactions of alcohols with aryl halides [J].
Altman, Ryan A. ;
Shafir, Alexandr ;
Choi, Alice ;
Lichtor, Phillip A. ;
Buchwald, Stephen L. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (01) :284-286
[2]   Copper-catalyzed N-arylation of imidazoles and benzimidazoles [J].
Altman, Ryan A. ;
Koval, Erica D. ;
Buchwald, Stephen L. .
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 [J].
Altman, Ryan A. ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2006, 8 (13) :2779-2782
[4]   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
[5]   Mild Conditions for Copper-Catalyzed N-Arylation of Imidazoles [J].
Chen, Huaming ;
Wang, Deping ;
Wang, Xianyang ;
Huang, Wenlong ;
Cai, Qian ;
Ding, Ke .
SYNTHESIS-STUTTGART, 2010, (09) :1505-1511
[6]   Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis [J].
Evano, Gwilherm ;
Blanchard, Nicolas ;
Toumi, Mathieu .
CHEMICAL REVIEWS, 2008, 108 (08) :3054-3131
[7]   Formation of aryl-nitrogen, aryl-oxygen, and aryl-carbon bonds using well-defined copper(I)-based catalysts [J].
Gujadhur, RK ;
Bates, CG ;
Venkataraman, D .
ORGANIC LETTERS, 2001, 3 (26) :4315-4317
[8]   Efficient copper-promoted N-arylations of aryl halides with amines [J].
Huang, He ;
Yan, Xiuhua ;
Zhu, Weiliang ;
Liu, Hong ;
Jiang, Hualiang ;
Chen, Kaixian .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (05) :617-619
[9]   An efficient copper-catalyzed coupling of aryl halides with imidazoles [J].
Kiyomori, A ;
Marcoux, JF ;
Buchwald, SL .
TETRAHEDRON LETTERS, 1999, 40 (14) :2657-2660
[10]   Mild copper-catalyzed N-arylation of azaheterocycles with aryl halides [J].
Kuil, M ;
Bekedam, EK ;
Visser, GM ;
van den Hoogenband, A ;
Terpstra, JW ;
Kamer, PCJ ;
van Leeuwen, PWNM ;
van Strijdonck, GPF .
TETRAHEDRON LETTERS, 2005, 46 (14) :2405-2409