Dearomatization of Indoles via Palladium-Catalyzed Allylic C-H Activation

被引：38
作者：
Zhang, Heng [1 ]
Hu, Rong-Bin [1 ]
Liu, Na [1 ]
Li, Shi-Xia [1 ]
Yang, Shang-Dong [1 ,2 ]
机构：
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 01期
关键词：
AEROBIC OXIDATIVE AMINATION; CARBON BOND FORMATION; ASYMMETRIC DEAROMATIZATION; ENANTIOSELECTIVE SYNTHESIS; TERMINAL ALKENES; SELECTIVE FUNCTIONALIZATION; ARYLATIVE DEAROMATIZATION; EFFICIENT SYNTHESIS; N-ALLOC; CONSTRUCTION;
D O I：
10.1021/acs.orglett.5b03053
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first Pd-catalyzed allylic dearomatization of substituted indoles triggered by C-H bond activation is reported. The presence of a catalytic amount of 2,5-DMBQ is proven to be a key factor for the high yield. This one-pot tandem allylic C-H activation/dearomatization sequence provides a straightforward access to 3,3-disubstituted indolines.
引用
收藏
页码：28 / 31
页数：4
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  • [1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations
    Ackermann, Lutz
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) : 281 - 295
  • [2] 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
  • [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] Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: Synthesis of (-)-flustramine B
    Austin, JF
    Kim, SG
    Sinz, CJ
    Xiao, WJ
    MacMillan, DWC
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5482 - 5487
  • [5] EVIDENCE FOR (PI-ALLYL)PALLADIUM(II)(QUINONE) COMPLEXES IN THE PALLADIUM-CATALYZED 1,4-DIACETOXYLATION OF CONJUGATED DIENES
    BACKVALL, JE
    GOGOLL, A
    [J]. TETRAHEDRON LETTERS, 1988, 29 (18) : 2243 - 2246
  • [6] FeCl3-Mediated Friedel-Crafts Hydroarylation with Electrophilic N-Acetyl Indoles for the Synthesis of Benzofuroindolines
    Beaud, Rodolphe
    Guillot, Regis
    Kouklovsky, Cyrille
    Vincent, Guillaume
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (50) : 12546 - 12550
  • [7] Terminal Olefins to Linear α,β-Unsaturated Ketones: Pd(II)/Hypervalent Iodine Co-catalyzed Wacker Oxidation-Dehydrogenation
    Bigi, Marinus A.
    White, M. Christina
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (21) : 7831 - 7834
  • [8] Palladium-Catalyzed Allylic C-H Fluorination
    Braun, Marie-Gabrielle
    Doyle, Abigail G.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (35) : 12990 - 12993
  • [9] A concise and flexible total synthesis of (-)-diazonamide A
    Burgett, AWG
    Li, QY
    Wei, Q
    Harran, PG
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (40) : 4961 - 4966
  • [10] Palladium-catalyzed regioselective azidation of allylic C-H bonds under atmospheric pressure of dioxygen
    Chen, Huoji
    Yang, Wanfei
    Wu, Wanqing
    Jiang, Huanfeng
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (21) : 3340 - 3343
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