Flexible Gold-Catalyzed Regioselective Oxidative Difunctionalization of Unactivated Alkenes

被引:188
|
作者
de Haro, Teresa [1 ]
Nevado, Cristina [1 ]
机构
[1] Univ Zurich, Inst Organ Chem, CH-8006 Zurich, Switzerland
关键词
alkenes; amino alcohols; gold; homogeneous catalysis; oxidation; N-FLUOROBENZENESULFONIMIDE; REDUCTIVE ELIMINATION; BOND FORMATION; C-O; DIAMINATION; AMINOACETOXYLATION; AMINOHYDROXYLATION; NITRILES; AMINOOXYGENATION; DERIVATIVES;
D O I
10.1002/anie.201005763
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
AuI/AuIII catalytic cycles can trigger three highly regioselective alkene difunctionalization processes that involve the formation of C(sp3)iO, C(sp3)iN, and C(sp3)iC(sp 2) bonds. The reaction can proceed by reductive elimination on the oxidized gold center with complete retention of the configuration or through two subsequent nucleophilic substitution reactions via an aziridine intermediate. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:906 / 910
页数:5
相关论文
共 50 条
  • [1] Gold-catalyzed oxidative aminoesterification of unactivated alkenes
    Pascal Feige
    Teresa de Haro
    Giulia Rusconi
    Estibaliz Merino
    Cristina Nevado
    Monatshefte für Chemie - Chemical Monthly, 2018, 149 : 749 - 754
  • [2] Gold-catalyzed oxidative aminoesterification of unactivated alkenes
    Feige, Pascal
    de Haro, Teresa
    Rusconi, Giulia
    Merino, Estibaliz
    Nevado, Cristina
    MONATSHEFTE FUR CHEMIE, 2018, 149 (04): : 749 - 754
  • [3] Copper-Catalyzed Oxidative Difunctionalization of Terminal Unactivated Alkenes
    Hussain, Muhammad Ijaz
    Feng, Yangyang
    Hu, Liangzhen
    Deng, Qjngfu
    Zhang, Xiaohui
    Xiong, Yan
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (15): : 7852 - 7859
  • [4] Trinuclear Gold-Catalyzed 1,2-Difunctionalization of Alkenes
    Fang, Qing-Yun
    Han, Jie
    Qin, Mingzhe
    Li, Weipeng
    Zhu, Chengjian
    Xie, Jin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (34)
  • [5] Homogeneous Gold-Catalyzed Oxidative Carboheterofunctionalization of Alkenes
    Zhang, Guozhu
    Cui, Li
    Wang, Yanzhao
    Zhang, Liming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) : 1474 - +
  • [6] Gold-Catalyzed Anti-Markovnikov Selective Hydrothiolation of Unactivated Alkenes
    Tamai, Taichi
    Fujiwara, Keiko
    Higashimae, Shinya
    Nomoto, Akihiro
    Ogawa, Akiya
    ORGANIC LETTERS, 2016, 18 (09) : 2114 - 2117
  • [7] Regioselective palladium-catalyzed intramolecular oxidative aminofluorination of unactivated alkenes
    Wu, Tao
    Cheng, Jiashun
    Chen, Pinhong
    Liu, Guosheng
    CHEMICAL COMMUNICATIONS, 2013, 49 (77) : 8707 - 8709
  • [8] Metal-Free, n-Bu4NI-Catalyzed Regioselective Difunctionalization of Unactivated Alkenes
    Xue, Qicai
    Xie, Jin
    Xu, Pan
    Hu, Kaidong
    Cheng, Yixiang
    Zhu, Chengjian
    ACS CATALYSIS, 2013, 3 (06): : 1365 - 1368
  • [9] Oxidative Interception of the Hydroamination Pathway: A Gold-Catalyzed Diamination of Alkenes
    Iglesias, Alvaro
    Muniz, Kilian
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (40) : 10563 - 10569
  • [10] Oxidative 1,2-Difunctionalization of Ethylene via Gold-Catalyzed Oxyarylation
    Harper, Matthew J.
    Emmett, Edward J.
    Bower, John F.
    Russell, Christopher A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (36) : 12386 - 12389