Aromatic Cations from Oxidative Carbon-Hydrogen Bond Cleavage in Bimolecular Carbon-Carbon Bond Forming Reactions

被引：59
|
作者：
Clausen, Dane J. [1 ]
Floreancig, Paul E. [1 ]
机构：
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 15期
基金：
美国国家卫生研究院;
关键词：
CROSS-COUPLING REACTIONS; STEREOSELECTIVE-SYNTHESIS; CHROMENE ACETALS; DDQ; ETHERS; CYCLIZATION; PRINS; ACTIVATION; CATALYSIS; ALDEHYDES;
D O I：
10.1021/jo301185h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chromenes and isochromenes react quickly with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to form persistent aromatic oxocarbenium ions through oxidative carbon-hydrogen cleavage. This process is tolerant of electron-donating and electron-withdrawing groups on the benzene ring and additional substitution on the pyran ring. A variety of nucleophiles can be added to these cations to generate a diverse set of structures.
引用
收藏
页码：6574 / 6582
页数：9
相关论文
共 50 条
  • [31] Acetylene Radical-Cations in Carbon-Carbon Bond Forming Reactio
    Vasilyev, Aleksander V.
    MINI-REVIEWS IN ORGANIC CHEMISTRY, 2017, 14 (03) : 204 - 216
  • [32] Carbon-Carbon Bond Forming Reactions via Photogenerated Intermediates
    Ravelli, Davide
    Protti, Stefano
    Fagnoni, Maurizio
    CHEMICAL REVIEWS, 2016, 116 (17) : 9850 - 9913
  • [33] CARBON-CARBON BOND FORMING REACTIONS VIA METAL HOMOENOLATES
    NAKAMURA, E
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1989, 47 (10) : 931 - 938
  • [34] Recent Developments on Carbon-Carbon Bond Forming Reactions in Water
    Chaturvedi, Devdutt
    Barua, Nabin C.
    CURRENT ORGANIC SYNTHESIS, 2012, 9 (01) : 17 - 30
  • [35] The development of carbon-carbon bond forming reactions of aminal radicals
    Schiedler, David A.
    Vellucci, Jessica K.
    Lu, Yi
    Beaudry, Christopher M.
    TETRAHEDRON, 2015, 71 (09) : 1448 - 1465
  • [36] Carbon-carbon bond forming solid-phase reactions
    Lorsbach, BA
    Kurth, MJ
    CHEMICAL REVIEWS, 1999, 99 (06) : 1549 - 1581
  • [37] Activation of a cyclobutanone carbon-carbon bond over an aldehyde carbon-hydrogen bond in the rhodium-catalyzed decarbonylation
    Matsuda, T
    Shigeno, M
    Murakami, M
    CHEMISTRY LETTERS, 2006, 35 (03) : 288 - 289
  • [38] CARBON-HYDROGEN VERSUS CARBON-CARBON BOND-CLEAVAGE OF 1,2-DIARYLETHANES IN ACETONITRILE-WATER
    CAMAIONI, DM
    FRANZ, JA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1983, 185 (MAR): : 61 - ORGN
  • [39] Oxidative Cleavage of the Carbon-Carbon σ-Bond Using Reusable Copper on Iron
    Song, Ren-Jie
    Liu, Yu
    Hu, Rui-Xiang
    Liu, Yan-Yun
    Wu, Ji-Cheng
    Yang, Xu-Heng
    Li, Jin-Heng
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (09) : 1467 - 1473
  • [40] OXIDATIVE SECO REARRANGEMENT - A NOVEL CARBON-CARBON BOND-CLEAVAGE
    TROST, BM
    HIROI, K
    JUNGHEIM, LN
    JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (10): : 1839 - 1847
12345