Selective palladium-catalyzed aminations on dichloropyridines

被引:87
作者
Jonckers, THM [1 ]
Maes, BUW [1 ]
Lemière, GLF [1 ]
Dommisse, R [1 ]
机构
[1] Univ Antwerp, RUCA, Dept Chem, B-2020 Antwerp, Belgium
关键词
aminations; palladium; pyridines; heteroaromatic amines; regioselectivity;
D O I
10.1016/S0040-4020(01)00659-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed amination proved to be a valuable strategy for the selective introduction of aromatic and heteroaromatic amines, including aminopyridines and aminodiazines, on dichloropyridines. The use of mild amination conditions resulted in maximum selectivity and excellent base sensitive functional group tolerance. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7027 / 7034
页数:8
相关论文
共 48 条
[1]   Mechanistic studies of the palladium-catalyzed amination of aryl halides and the oxidative addition of aryl bromides to Pd(BINAP)2 and Pd(DPPF)2:: An unusual case of zero-order kinetic behavior and product inhibition [J].
Alcazar-Roman, LM ;
Hartwig, JF ;
Rheingold, AL ;
Liable-Sands, LM ;
Guzei, IA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (19) :4618-4630
[2]  
Baranano D, 1997, CURR ORG CHEM, V1, P287
[3]  
BRODY F, 1960, PYRIDINE ITS DERIV 1
[4]   Oxidative effects of nickel on bone marrow and blood of rats [J].
Chen, CY ;
Sheu, JY ;
Lin, TH .
JOURNAL OF TOXICOLOGY AND ENVIRONMENTAL HEALTH-PART A, 1999, 58 (08) :475-483
[5]   A very convenient dimethylamination of activated aromatic halides using N,N-dimethylformamide and ethanolamines [J].
Cho, YH ;
Park, JC .
TETRAHEDRON LETTERS, 1997, 38 (48) :8331-8334
[6]   Facile palladium-mediated substitution of chlorine in 2-chloroquinolines [J].
Ciufolini, MA ;
Mitchell, JW ;
Roschangar, F .
TETRAHEDRON LETTERS, 1996, 37 (46) :8281-8284
[7]  
COMINS DL, 1996, 6 MEMBERED RINGS 1 H, V5, P37
[8]   Nickel-catalysed synthesis of 3-chloroanilines and chloro aminopyridines via cross-coupling reactions of aryl and heteroaryl dichlorides with amines [J].
Desmarets, C ;
Schneider, R ;
Fort, Y .
TETRAHEDRON LETTERS, 2001, 42 (02) :247-250
[9]   ADDITION OF ARYL HALIDES TO TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(0) [J].
FITTON, P ;
RICK, EA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1971, 28 (02) :287-&
[10]  
Frost CG, 1998, J CHEM SOC PERK T 1, P2615