Anodic Oxidation and Organocatalysis: Direct Regio- and Stereoselective Access to meta-Substituted Anilines by α-Arylation of Aldehydes

被引：156
作者：
Jensen, Kim L. [1 ]
Franke, Patrick T. [1 ]
Nielsen, Lasse T. [1 ]
Daasbjerg, Kim [1 ]
Jorgensen, Karl Anker [1 ]
机构：
[1] Aarhus Univ, Ctr Catalysis, Dept Chem, DK-8000 Aarhus C, Denmark
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 01期
基金：
新加坡国家研究基金会;
关键词：
aldehydes; aromatic compounds; dihydrobenzofurans; electrochemistry; organocatalysis; ELECTROCHEMICAL SYNTHESIS; ASYMMETRIC-SYNTHESIS; ALPHA; BETA-UNSATURATED ALDEHYDES; ENANTIOSELECTIVE SYNTHESIS; MICHAEL REACTIONS; CATALYSIS; CASCADE; DERIVATIVES; ALKYLATION; CHEMISTRY;
D O I：
10.1002/anie.200904754
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Figure presented) What's the potential? An anodic oxidation/ organocatalytic α-arylation of aldehydes using substituted electron-rich aromatic compounds has been developed. The method gives access to meta-substituted anilines and dihydrobenzofurans in good yields and excellent enantioselectivity (see scheme; Pg=protecting group). This method is an example of a new concept combining organocatalysis with electrochemistry. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：129 / 133
页数：5
相关论文
共 80 条
  • [71] Synthesis of the hamigeran skeleton through an electro-oxidative coupling reaction
    Sperry, JB
    Wright, DL
    [J]. TETRAHEDRON LETTERS, 2005, 46 (03) : 411 - 414
  • [72] Sundén H, 2007, CHEM-EUR J, V13, P574, DOI 10.1002/chem.200600572
  • [73] Recent advances in asymmetric organocatalytic 1,4-conjugate additions
    Tsogoeva, Svetlana B.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (11) : 1701 - 1716
  • [74] Vo G. D., 2008, ANGEW CHEM, V120, P2157
  • [75] Palladium-catalyzed α-arylation of aldehydes with bromo- and chloroarenes catalyzed by [{Pd(allyl)Cl}2] and dppf or Q-phos
    Vo, Giang D.
    Hartwig, John E.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (11) : 2127 - 2130
  • [76] An enantioselective organocatalytic oxidative dearomatization strategy
    Vo, Ngoc T.
    Pace, Robert D. M.
    O'Hara, Fionn
    Gaunt, Matthew J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) : 404 - +
  • [77] Catalytic asymmetric reductive Michael cyclization
    Yang, JW
    Fonseca, MTH
    List, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (43) : 15036 - 15037
  • [78] Modern strategies in electroorganic synthesis
    Yoshida, Jun-ichi
    Kataoka, Kazuhide
    Horcajada, Roberto
    Nagaki, Aiichiro
    [J]. CHEMICAL REVIEWS, 2008, 108 (07) : 2265 - 2299
  • [79] One-Pot Electrochemical Synthesis of Fused Indole Derivatives Containing Active Hydroxyl Groups in Aqueous Medium
    Zeng, Cheng-Chu
    Liu, Fu-Jian
    Ping, Da-Wei
    Hu, Li-Ming
    Cai, Yuan-Li
    Zhong, Ru-Gang
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) : 6386 - 6389
  • [80] Organocatalytic Enantioselective Aminosulfenylation of α,β-Unsaturated Aldehydes
    Zhao, Gui-Ling
    Rios, Ramon
    Vesely, Jan
    Eriksson, Lars
    Cordova, Armando
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (44) : 8468 - 8472
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