Efficient copper-catalyzed amination of aryl halides with amines and N-H heterocycles using rac-BINOL as ligand

被引:62
作者
Zhu, Di [1 ]
Wang, Rongliang [1 ]
Mao, Jincheng [1 ]
Xu, Lei [1 ]
Wu, Fan [1 ]
Wan, Boshun [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
关键词
Amination; copper; aryl halides; cross-coupling; rac-BINOL; ligand;
D O I
10.1016/j.molcata.2006.05.005
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A highly efficient copper-catalyzed system using commercially available racemic 1,1'-binaphthyl-2,2'-diol (rac-BINOL) as the ligand was developed for amination of aryl halides and heteroaryl halides with alkyl amines and N-H heterocycles. Good to high yields were obtained for aryl bromides and heteroaryl chlorides. The commercially available rac-BINOL ligand with excellent stability and high efficiency for aryl bromides and heteroaryl chlorides ultimately make this protocol of potentially practical utility. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:256 / 260
页数:5
相关论文
共 74 条
  • [1] The copper-catalyzed N-arylation of indoles
    Antilla, JC
    Klapars, A
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) : 11684 - 11688
  • [2] Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles
    Antilla, JC
    Baskin, JM
    Barder, TE
    Buchwald, SL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) : 5578 - 5587
  • [3] Palladium-catalyzed intramolecular α-arylation of sulfoximines
    Bolm, C
    Okamura, H
    Verrucci, M
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 687 (02) : 444 - 450
  • [4] Bolm C, 2002, SYNLETT, P832
  • [5] BINOL: A versatile chiral reagent
    Brunel, JM
    [J]. CHEMICAL REVIEWS, 2005, 105 (03) : 857 - 897
  • [6] Efficient Pd-catalyzed amination of heteroaryl halides
    Charles, MD
    Schultz, P
    Buchwald, SL
    [J]. ORGANIC LETTERS, 2005, 7 (18) : 3965 - 3968
  • [7] Palladium-catalyzed α-arylation of sulfoximines
    Cho, GY
    Bolm, C
    [J]. ORGANIC LETTERS, 2005, 7 (07) : 1351 - 1354
  • [8] Copper-mediated cross-coupling reactions of N-unsubstituted sulfoximines and aryl halides
    Cho, GY
    Rémy, P
    Jansson, J
    Moessner, C
    Bolm, C
    [J]. ORGANIC LETTERS, 2004, 6 (19) : 3293 - 3296
  • [9] Design and evolution of copper apatite catalysts for N-arylation of heterocycles with chloro- and fluoroarenes
    Choudary, BM
    Sridhar, C
    Kantam, ML
    Venkanna, GT
    Sreedhar, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) : 9948 - 9949
  • [10] Clement JB, 2001, SYNLETT, P1423