Oxazolidin-2-one as Efficient Ligand for the Copper-Catalyzed N-Arylation of Pyrrole, Imidazole and Indole

被引:9
作者
Ma, Hengchang [1 ]
Wu, Shang [1 ]
Sun, Qiangsheng [1 ]
Lei, Ziqiang [1 ]
机构
[1] NW Normal Univ, Key Lab Polymer Mat Gansu Prov, Key Lab Ecoenvironm Related Polymer Mat, Coll Chem & Chem Engn,Minist Educ, Lanzhou 730070, Peoples R China
基金
中国国家自然科学基金;
关键词
Copper; coupling; catalysis; ligands; arylations; NITROGEN-CONTAINING HETEROCYCLES; ARYL HALIDES; COUPLING REACTION; HIGHLY EFFICIENT; C-N; ESTROGEN-RECEPTOR; EXCELLENT LIGAND; BOND FORMATION; AMINO-ACIDS; AMIDATION;
D O I
10.2174/157017810791112496
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxazolidin-2-one was found to be a facile ligand for the N-arylation of pyrrole, indole, and imidazole with aryl and heteroaryl iodides, bromides, and chlorides by applying CuI as catalyst. The easy preparation, commercial availability, lower molecular weight, and broad substrate applicability, as well as substituent compatibility of this catalysis system render oxazolidin-2-one great advantages over the Cu-catalyzed methods that have already been utilized in a number of applications.
引用
收藏
页码:212 / 218
页数:7
相关论文
共 44 条
[1]   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
[2]   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
[3]   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
[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]   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
[6]   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
[7]   An inexpensive and efficient copper catalyst for N-arylation of amines, Amides and nitrogen-containing heterocycles [J].
Guo, Xun ;
Rao, Honghua ;
Fu, Hua ;
Jiang, Yuyang ;
Zhao, Yufen .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (15) :2197-2202
[8]  
Hartwig JF, 1998, ANGEW CHEM INT EDIT, V37, P2046, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO
[9]  
2-L
[10]   Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].
Hassan, J ;
Sévignon, M ;
Gozzi, C ;
Schulz, E ;
Lemaire, M .
CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469