Palladium catalyzed alkylation of indole via aliphatic C-H bond activation of tertiary amine

被引：36
作者：
Ramachandiran, K. [1 ]
Muralidharan, D. [1 ]
Perumal, P. T. [1 ]
机构：
[1] Cent Leather Res Inst CSIR, Div Organ Chem, Madras 600020, Tamil Nadu, India
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 28期
关键词：
Palladium; C-H activation; 1,1-Bis-indolymethane; C-C coupling; Alkylation of indole; DIRECT ARYLATION; NITROGEN ATOM; DIRECT FUNCTIONALIZATION; MECHANISTIC ASPECTS; EFFICIENT SYNTHESIS; COPPER; DERIVATIVES; COMPLEXES; ALDEHYDES; ALKENYLATION;
D O I：
10.1016/j.tetlet.2011.04.110
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Alkylation of indoles has been achieved via Pd-catalyzed aliphatic C-H bond activation of tertiary amine coupling with indole followed by C-N bond cleavage and subsequent addition of indole. This method involves the migration of alkane chain from tertiary amine to indole. (C) 2011 Elsevier Ltd. All rights reserved.
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收藏
页码：3579 / 3583
页数：5
相关论文
共 55 条
  • [11] Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds
    Daugulis, Olafs
    Do, Hien-Quang
    Shabashov, Dmitry
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) : 1074 - 1086
  • [12] Copper-catalyzed arylation of heterocycle C-H bonds
    Do, Hien-Quang
    Daugulis, Olafs
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (41) : 12404 - +
  • [13] Doye S, 2001, ANGEW CHEM INT EDIT, V40, P3351, DOI 10.1002/1521-3773(20010917)40:18<3351::AID-ANIE3351>3.0.CO
  • [14] 2-B
  • [15] Dyker G, 2005, HANDBOOK OF C-H TRANSFORMATIONS: APPLICATIONS IN ORGANIC SYNTHESIS, VOL 1, pV
  • [16] 6-BROMOTRYPTAMINE DERIVATIVES FROM THE GULF OF CALIFORNIA TUNICATE DIDEMNUM-CANDIDUM
    FAHY, E
    POTTS, BCM
    FAULKNER, DJ
    SMITH, K
    [J]. JOURNAL OF NATURAL PRODUCTS, 1991, 54 (02): : 564 - 569
  • [17] Indolyl carboxylic acids by condensation of indoles with α-keto acids
    Garbe, TR
    Kobayashi, M
    Shimizu, N
    Takesue, N
    Ozawa, M
    Yukawa, H
    [J]. JOURNAL OF NATURAL PRODUCTS, 2000, 63 (05): : 596 - 598
  • [18] One-Pot Synthesis of Symmetric and Unsymmetric 1,1-Bis-indolylmethanes via Tandem Iron-Catalyzed C-H Bond Oxidation and C-O Bond Cleavage
    Guo, Xingwei
    Pan, Shiguang
    Liu, Jinhua
    Li, Zhiping
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22) : 8848 - 8851
  • [19] Catalytic and highly regioselective cross-coupling of aromatic C-H substrates
    Hull, Karni L.
    Sanford, Melanie S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) : 11904 - +
  • [20] Catalytic C-H/olefin coupling
    Kakiuchi, F
    Murai, S
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (10) : 826 - 834
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