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.
引用
收藏
页码：3579 / 3583
页数：5
相关论文
共 55 条
  • [1] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
    Ackermann, Lutz
    Vicente, Ruben
    Kapdi, Anant R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
  • [2] Ruthenium-Catalyzed Regioselective Direct Alkylation of Arenes with Unactivated Alkyl Halides through C-H Bond Cleavage
    Ackermann, Lutz
    Novak, Petr
    Vicente, Ruben
    Hofmann, Nora
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (33) : 6045 - 6048
  • [3] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
    Alberico, Dino
    Scott, Mark E.
    Lautens, Mark
    [J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
  • [4] Fluoroboric acid adsorbed on silica gel catalyzed synthesis of bisindolyl alkanes under mild and solvent-free conditions
    Bandgar, B. P.
    Patil, Abasaheb. V.
    Kamble, V. T.
    [J]. ARKIVOC, 2007, : 252 - 259
  • [5] Twofold C-H functionalization:: Palladium-catalyzed ortho arylation of anilides
    Brasche, Gordon
    Garcia-Fortanet, Jorge
    Buchwald, Stephen L.
    [J]. ORGANIC LETTERS, 2008, 10 (11) : 2207 - 2210
  • [6] Biaryl synthesis via direct arylation: Establishment of an efficient catalyst for intramolecular processes
    Campeau, LC
    Parisien, M
    Leblanc, M
    Fagnou, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) : 9186 - 9187
  • [7] The oxidative Mannich reaction catalyzed by dirhodium caprolactamate
    Catino, AJ
    Nichols, JM
    Nettles, BJ
    Doyle, MP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (17) : 5648 - 5649
  • [8] Rh(II)-Catalyzed intermolecular oxidative sulfamidation of aldehydes:: A mild efficient synthesis of N-sulfonylcarboxamides
    Chan, Johann
    Baucorn, Kyle D.
    Murry, Jerry A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (46) : 14106 - +
  • [9] Carbonylation at sp3 C-H bonds adjacent to a nitrogen atom in alkylamines catalyzed by rhodium complexes
    Chatani, N
    Asaumi, T
    Ikeda, T
    Yorimitsu, S
    Ishii, Y
    Kakiuchi, F
    Murai, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) : 12882 - 12883
  • [10] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality
    Chen, Xiao
    Engle, Keary M.
    Wang, Dong-Hui
    Yu, Jin-Quan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) : 5094 - 5115
123456