Nickel (0)/dihydroimidazol-2-ylidene complex catalyzed coupling of aryl chlorides and amines

被引:202
作者
Desmarets, C [1 ]
Schneider, R [1 ]
Fort, Y [1 ]
机构
[1] Univ Nancy 1, UMR 7565, Fac Sci, F-54506 Vandoeuvre Les Nancy, France
关键词
D O I
10.1021/jo016352l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general and simple nickel-catalyzed coupling of aryl chlorides and amines is reported. The scope and limitations of the coupling process using Ni(0), 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene, and NaO-t-Bu as base were investigated. Secondary cyclic and acyclic amines and anilines provided the arylamine coupling products in good to excellent yields. Compared to palladium-catalyzed aminations, this procedure offers an alternative route to N-substituted anilines starting from readily available aryl chlorides.
引用
收藏
页码:3029 / 3036
页数:8
相关论文
共 83 条
  • [51] 2-C
  • [52] Lipshutz BH, 2000, ANGEW CHEM INT EDIT, V39, P4492, DOI 10.1002/1521-3773(20001215)39:24<4492::AID-ANIE4492>3.3.CO
  • [53] 2-#
  • [54] Synthesis of N-arylated oxazolidinones via a palladium catalyzed cross coupling reaction.: Application to the synthesis of the antibacterial agent Dup-721
    Madar, DJ
    Kopecka, H
    Pireh, D
    Pease, J
    Pliushchev, M
    Sciotti, RJ
    Wiedeman, PE
    Djuric, SW
    [J]. TETRAHEDRON LETTERS, 2001, 42 (22) : 3681 - 3684
  • [55] Palladium(II) complexes containing mono-, bi- and tridentate carbene ligands. Synthesis, characterisation and application as catalysts in C-C coupling reactions
    Magill, AM
    McGuinness, DS
    Cavell, KJ
    Britovsek, GJP
    Gibson, VC
    White, AJP
    Williams, DJ
    White, AH
    Skelton, BW
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) : 546 - 560
  • [56] C-C bond activation with selective functionalization: preparation of unsymmetrical biaryls from benzonitriles
    Miller, JA
    [J]. TETRAHEDRON LETTERS, 2001, 42 (40) : 6991 - 6993
  • [57] NEGWER M, 1994, ORGANIC DRUGS THEIR
  • [58] A highly active catalyst for palladium-catalyzed cross-coupling reactions: Room-temperature Suzuki couplings and amination of unactivated aryl chlorides
    Old, DW
    Wolfe, JP
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (37) : 9722 - 9723
  • [59] Ortner B, 2001, ANGEW CHEM INT EDIT, V40, P1283, DOI 10.1002/1521-3773(20010401)40:7<1283::AID-ANIE1283>3.0.CO
  • [60] 2-#