Efficient Copper-Catalyzed N-Arylation of Amides and Imidazoles with Aryl Iodides

被引:30
作者
Ali, Md. Ashif [1 ]
Saha, Prasenjit [1 ]
Punniyamurthy, Tharmalingam [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Gauhati 781039, India
来源
SYNTHESIS-STUTTGART | 2010年 / 06期
关键词
N-arylation; amides; imidazoles; copper iodide; TBAB; CROSS-COUPLING REACTIONS; C-N; HETEROARYL HALIDES; SUZUKI-MIYAURA; IONIC LIQUIDS; LIGAND; AMIDATION; VERSATILE; DISCOVERY; CHLORIDES;
D O I
10.1055/s-0029-1218643
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The C-N cross-coupling of amides and imidazoles with aryl iodides is described using CuI in tetrabutylammonium bromide (TBAB) under ligand-free conditions. The reaction is simple, general, and efficient affording the C-N cross-coupled products in shorter time and in high yield.
引用
收藏
页码:908 / 910
页数:3
相关论文
共 31 条
[21]   Catalysis in ionic liquids [J].
Parvulescu, Vasile I. ;
Hardacre, Christopher .
CHEMICAL REVIEWS, 2007, 107 (06) :2615-2665
[22]   A versatile and efficient ligand for copper-catalyzed formation of C-N, C-o, and P-C bonds: Pyrrolidine-2-phosphonic acid phenyl monoester [J].
Rao, HH ;
Jin, Y ;
Fu, H ;
Jiang, YY ;
Zhao, YF .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (13) :3636-3646
[23]   Palladium-Catalyzed Synthesis of Diarylmethanes: Exploitation of Carbanionic Leaving Groups [J].
Schmink, Jason R. ;
Leadbeater, Nicholas E. .
ORGANIC LETTERS, 2009, 11 (12) :2575-2578
[24]   The role of chelating diamine ligands in the Goldberg reaction: A kinetic study on the copper-catalyzed amidation of aryl iodides [J].
Strieter, ER ;
Blackmond, DG ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (12) :4120-4121
[25]   Palladium charcoal-catalyzed Suzuki-Miyaura coupling to obtain arylpyridines and arylquinolines [J].
Tagata, T ;
Nishida, M .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9412-9415
[26]   Reusable Cu2O/PPh3/TBAB system for the cross-couplings of aryl halides and heteroaryl halides with terminal alkynes [J].
Tang, Bo-Xiao ;
Wang, Feng ;
Li, Jin-Heng ;
Xie, Ye-Xiang ;
Zhang, Man-Bo .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) :6294-6297
[27]   On a new formation-manner of diphenyl-amine-derivatives. [Preliminary announcement.] [J].
Ullmann, F .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1903, 36 :2382-2384
[28]   Benzotriazole: an excellent ligand for Cu-catalyzed N-arylation of imidazoles with aryl and heteroaryl halides [J].
Verma, Akhilesh Kumar ;
Singh, Jaspal ;
Sankar, V. Kasi ;
Chaudhary, Ritu ;
Chandra, Ramesh .
TETRAHEDRON LETTERS, 2007, 48 (24) :4207-4210
[29]   An ullmann coupling of aryl iodides and Amines using an air-stable diazaphospholane ligand [J].
Yang, Minghua ;
Liu, Fei .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (23) :8969-8971
[30]   Pd-catalyzed intermolecular amidation of aryl halides: The discovery that xantphos can be trans-chelating in a palladium complex [J].
Yin, JJ ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) :6043-6048