CuBr-catalyzed efficient alkynylation of sp3 C-H bonds adjacent to a nitrogen atom

被引:615
作者
Li, ZP [1 ]
Li, CJ [1 ]
机构
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
关键词
D O I
10.1021/ja0460763
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple and effective catalytic method to construct propargylamine was developed by using copper bromide and tert-BuOOH via a combination of sp3 C-H bond and sp C-H bond activations followed by C-C bond formation. Copyright © 2004 American Chemical Society.
引用
收藏
页码:11810 / 11811
页数:2
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共 37 条
  • [1] A new method of synthesis for propargylic amines and ethers via benzotriazole derivatives using sodium dialkynyldiethylaluminates
    Ahn, JH
    Joung, MJ
    Yoon, NM
    Oniciu, DC
    Katritzky, AR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (02) : 488 - 492
  • [2] SELECTIVE INTERMOLECULAR CARBON-HYDROGEN BOND ACTIVATION BY SYNTHETIC METAL-COMPLEXES IN HOMOGENEOUS SOLUTION
    ARNDTSEN, BA
    BERGMAN, RG
    MOBLEY, TA
    PETERSON, TH
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (03) : 154 - 162
  • [3] Copper-catalyzed coupling of imines, acid chlorides, and alkynes: A multicomponent route to propargylamides
    Black, DA
    Arndtsen, BA
    [J]. ORGANIC LETTERS, 2004, 6 (07) : 1107 - 1110
  • [4] Ru3(CO)12-catalyzed coupling reaction of sp3 C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes
    Chatani, N
    Asaumi, T
    Yorimitsu, S
    Ikeda, T
    Kakiuchi, F
    Murai, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) : 10935 - 10941
  • [5] Thermal, catalytic, regiospecific functionalization of alkanes
    Chen, HY
    Schlecht, S
    Semple, TC
    Hartwig, JF
    [J]. SCIENCE, 2000, 287 (5460) : 1995 - 1997
  • [6] Selective functionalization of amino acids in water: A synthetic method via catalytic C-H bond activation
    Dangel, BD
    Johnson, JA
    Sames, D
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (33) : 8149 - 8150
  • [7] Double C-H activation strategy for the asymmetric synthesis of C2-Symmetric anilines
    Davies, HML
    Jin, QH
    [J]. ORGANIC LETTERS, 2004, 6 (11) : 1769 - 1772
  • [8] Cross-coupling of sp3 C-H bonds and alkenes:: Catalytic cyclization of alkene-amide substrates
    DeBoef, B
    Pastine, SJ
    Sames, D
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (21) : 6556 - 6557
  • [9] A ONE-STEP ROUTE TO 4-HYDROXY-2,3-DIARYL-3,4-DIHYDRO-1 (2H)-ISOQUINOLONES
    DODSWORTH, DJ
    CALIAGNO, MP
    EHRMANN, UE
    SAMMES, PG
    [J]. TETRAHEDRON LETTERS, 1980, 21 (52) : 5075 - 5078
  • [10] Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO