Nickel-catalysed sequential amination of aryl- and heteroaryl di- and trichlorides

被引:30
作者
Desmarets, C [1 ]
Schneider, R [1 ]
Fort, Y [1 ]
机构
[1] Univ Nancy 1, Fac Sci Synth Organ & React, UMR CNRS UHP 7565, F-54506 Vandoeuvre Les Nancy, France
关键词
nickel-catalysed amination; aryl trichlorides; diamino-benzenes; diamino-pyridines; triamino-pyridines;
D O I
10.1016/S0040-4020(01)00730-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Unsymmetrical 1,3-diaminobenzenes and diaminopyridines, were efficiently prepared by reaction of 3-chloroanilines and chloro-aminopyridines with amines via a nickel-catalysed amination. The Ni/2,2'-bipyridine catalyst is also effective for the sequential amination of aryl trichlorides. After a first selective monoamination of 1,3,5-trichlorobenzene, the obtained 3,5-dichloroanilines were subsequently transformed into novel and unsymmetrical 1,3,5-triaminobenzenes. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7657 / 7664
页数:8
相关论文
共 46 条
  • [1] Light-harvesting dendrimers
    Adronov, A
    Fréchet, JMJ
    [J]. CHEMICAL COMMUNICATIONS, 2000, (18) : 1701 - 1710
  • [2] An improved method for the palladium-catalyzed amination of aryl iodides
    Ali, MH
    Buchwald, SL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) : 2560 - 2565
  • [3] Catalytic asymmetric borane reduction of prochiral ketones by the use of chiral β-diamines
    Asami, M
    Sato, S
    Watanabe, H
    [J]. CHEMISTRY LETTERS, 2000, (09) : 990 - 991
  • [4] Palladium-catalyzed amination of aryl dibromides with secondary amines: synthetic and mechanistic aspects
    Beletskaya, IP
    Bessmertnykh, AG
    Guilard, R
    [J]. TETRAHEDRON LETTERS, 1999, 40 (35) : 6393 - 6397
  • [5] Recent synthetic advances in the nucleophilic amination of benzenes
    Belfield, AJ
    Brown, GR
    Foubister, AJ
    [J]. TETRAHEDRON, 1999, 55 (38) : 11399 - 11428
  • [6] Palladium-catalyzed N-arylation of sulfoximines with aryl bromides and aryl iodides
    Bolm, C
    Hildebrand, JP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (01) : 169 - 175
  • [7] Synthesis of biologically active N2-amine adducts of 2′-deoxyguanosine
    Bonala, RR
    Shishkina, IG
    Johnson, F
    [J]. TETRAHEDRON LETTERS, 2000, 41 (38) : 7281 - 7284
  • [8] Nickel-mediated amination chemistry.: Part 2:: Selective N-arylation or N,N′-diarylation of piperazine
    Brenner, E
    Schneider, R
    Fort, Y
    [J]. TETRAHEDRON LETTERS, 2000, 41 (16) : 2881 - 2884
  • [9] Nickel-catalysed couplings of aryl chlorides with secondary amines and piperazines
    Brenner, E
    Schneider, R
    Fort, Y
    [J]. TETRAHEDRON, 1999, 55 (44) : 12829 - 12842
  • [10] New efficient nickey(0) catalysed amination of aryl chlorides
    Brenner, E
    Fort, Y
    [J]. TETRAHEDRON LETTERS, 1998, 39 (30) : 5359 - 5362