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
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
  • [21] Dalko P.I., 2007, ENANTIOSELECTIVE ORG
  • [22] In the golden age of organocatalysis
    Dalko, PI
    Moisan, L
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) : 5138 - 5175
  • [23] DALKO PI, 2007, CHEM REV, V107
  • [24] de Figueiredo R. M., 2008, ANGEW CHEM, V120, P1472
  • [25] Amine-catalyzed cyclizations of tethered α,β-unsaturated carbonyl compounds
    de Figueiredo, Renata Marcia
    Froehlich, Roland
    Christmann, Mathias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (08) : 1450 - 1453
  • [26] Donnelly D.M.X., 1984, COMPREHENSIVE HETERO, P705
  • [27] Enders D., 2008, ANGEW CHEM, V120, P7649, DOI DOI 10.1002/ANGE.200802532
  • [28] Enders D., 2007, Angew. Chem, V119, P1590, DOI DOI 10.1002/ange.200603129
  • [29] Organocatalytic asymmetric domino reactions:: A cascade consisting of a Michael addition and an aldehyde α-alkylation
    Enders, Dieter
    Wang, Chuan
    Bats, Jan W.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (39) : 7539 - 7542
  • [30] Asymmetric organocatalytic domino reactions
    Enders, Dieter
    Grondal, Christoph
    Huettl, Matthias R. M.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) : 1570 - 1581