Nano ceria catalyzed Ullmann type coupling reactions

被引:29
作者
Agawane, Sandeep M. [1 ]
Nagarkar, Jayashree M. [1 ]
机构
[1] Inst Chem Technol, Dept Chem, Bombay 400019, Maharashtra, India
关键词
Nano ceria; Synthesis and characterization; Ullmann type coupling; Copper and ligand free; Heterogeneous catalysis; ARYL IODIDES; C-N; O-ARYLATION; EFFICIENT; LIGAND; COPPER; VERSATILE; HALIDES; PHENOLS; THIOLS;
D O I
10.1016/j.tetlet.2011.07.117
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ullmann type intermolecular coupling of aryl halide with hetero-aromatic compounds, such as phenols, amines, and thiophenols are key reactions for the formation of carbon-heteroatom bond in organic synthesis. We report a robust and novel method that provides an efficient and economic route for the synthesis of O, N, and S-arylation via Ullman coupling by using nano cerium oxide (ceria, CeO2). CeO2 is a cheaper catalyst compared to related copper based catalysts. This method provides a wide range of substrate applicability in the case of phenols and amines. Less reactive chlorobenzene substituted with strong electron withdrawing groups such as 4-nitrochlorobenzene and 4-cyanochlorobenzene favor the reaction. This protocol avoids the use of ligand and gives arylated product in satisfactory yields. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5220 / 5223
页数:4
相关论文
共 34 条
[1]   Nano ceria catalyzed synthesis of α-aminophosphonates under ultrasonication [J].
Agawane, Sandeep M. ;
Nagarkar, Jayashree M. .
TETRAHEDRON LETTERS, 2011, 52 (27) :3499-3504
[2]   Rapid Ullmann-type synthesis of aryl sulfides using a copper(I) catalyst and ligand under microwave irradiation [J].
Bagley, Mark C. ;
Dix, Matthew C. ;
Fusillo, Vincenzo .
TETRAHEDRON LETTERS, 2009, 50 (26) :3661-3664
[3]   Palladium-catalysed cross-coupling and related reactions involving pyrroles [J].
Banwell, Martin G. ;
Goodwin, Thomas E. ;
Ng, Sarah ;
Smith, Jason A. ;
Wong, David J. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (14) :3043-3060
[4]   Inhibitors of apoptosis in lymphocytes:: Synthesis and biological evaluation of compounds related to pifithrin-α [J].
Barchéchath, SD ;
Tawatao, RI ;
Corr, M ;
Carson, DA ;
Cottam, HB .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (20) :6409-6422
[5]   A general method for the formation of aryl-sulfur bonds using copper(I) catalysts [J].
Bates, CG ;
Gujadhur, RK ;
Venkataraman, D .
ORGANIC LETTERS, 2002, 4 (16) :2803-2806
[6]   Synthesis of dimethyl carbonate and glycols from carbon dioxide, epoxides, and methanol using heterogeneous basic metal oxide catalysts with high activity and selectivity [J].
Bhanage, BM ;
Fujita, S ;
Ikushima, Y ;
Arai, M .
APPLIED CATALYSIS A-GENERAL, 2001, 219 (1-2) :259-266
[7]   Simple and efficient recyclable catalytic system for performing copper-catalysed S-arylation reactions in the presence of water [J].
Carril, Monica ;
SanMartin, Raul ;
Dominguez, Esther ;
Tellitu, Imanol .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (18) :5100-5105
[8]   1,1,1-tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod ligand for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols [J].
Chen, Yao-Jung ;
Chen, Hsin-Hung .
ORGANIC LETTERS, 2006, 8 (24) :5609-5612
[9]   CuI-catalyzed coupling reactions of aryl iodides and bromides with thiols promoted by amino acid ligands [J].
Deng, W ;
Zou, Y ;
Wang, YF ;
Liu, L ;
Guo, QX .
SYNLETT, 2004, (07) :1254-1258
[10]   A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols [J].
Fernández-Rodríguez, MA ;
Shen, QL ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2180-2181