Nickel-catalysed selective N-arylation or N,N′-diarylation of secondary diamines

被引:19
作者
Brenner, E [1 ]
Schneider, R [1 ]
Fort, Y [1 ]
机构
[1] Univ Nancy 1, UMR CNRS 7565, Fac Sci Synthese Organ & Reactivite, F-54506 Vandoeuvre Les Nancy, France
关键词
N-arylation; N; '-diarylation; secondary diamines; nickel catalysis;
D O I
10.1016/S0040-4020(02)00750-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The selective synthesis of N-aryl or N,N'-diaryl piperazines and trimethylene(bis)piperidines from the corresponding diamines and aryl chlorides using a catalyst combination of Ni(0) associated to 2,2'-bipyridine is described. The Ni/2,2'-bipyridine catalyst is also effective for the sequential arylation of piperazine. The preparation of novel and unsymmetrical 1,4-diaryl piperazines is reported. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6913 / 6924
页数:12
相关论文
共 50 条
[1]  
AM CYANAMID, 1960, Patent No. 3173917
[2]   Recent synthetic advances in the nucleophilic amination of benzenes [J].
Belfield, AJ ;
Brown, GR ;
Foubister, AJ .
TETRAHEDRON, 1999, 55 (38) :11399-11428
[3]   Nickel-mediated amination chemistry.: Part 2:: Selective N-arylation or N,N′-diarylation of piperazine [J].
Brenner, E ;
Schneider, R ;
Fort, Y .
TETRAHEDRON LETTERS, 2000, 41 (16) :2881-2884
[4]   Nickel-catalysed couplings of aryl chlorides with secondary amines and piperazines [J].
Brenner, E ;
Schneider, R ;
Fort, Y .
TETRAHEDRON, 1999, 55 (44) :12829-12842
[5]   New efficient nickey(0) catalysed amination of aryl chlorides [J].
Brenner, E ;
Fort, Y .
TETRAHEDRON LETTERS, 1998, 39 (30) :5359-5362
[6]   1-(2-PYRIDINYL)PIPERAZINE DERIVATIVES WITH ANTIANAPHYLACTIC, ANTIBRONCHOSPASTIC, AND MAST-CELL STABILIZING ACTIVITIES [J].
CATTO, A ;
MOTTA, G ;
TAJANA, A ;
CAZZULANI, P ;
NARDI, D ;
LEONARDI, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (01) :13-19
[7]   Synthesis and antibacterial evaluation of certain quinolone derivatives [J].
Chen, YL ;
Fang, KC ;
Sheu, JY ;
Hsu, SL ;
Tzeng, CC .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (14) :2374-2377
[8]  
DANKWARDT SM, 1995, TETRAHEDRON LETT, V36, P4923, DOI 10.1016/0040-4039(95)00930-B
[9]   Nickel (0)/dihydroimidazol-2-ylidene complex catalyzed coupling of aryl chlorides and amines [J].
Desmarets, C ;
Schneider, R ;
Fort, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09) :3029-3036
[10]   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