Copper Salts as Additives in Gold(I)-Catalyzed Reactions

被引:81
作者
Guerinot, Amandine [1 ]
Fang, Weizhen [1 ]
Sircoglou, Marie [1 ]
Bour, Christophe [1 ]
Bezzenine-Lafollee, Sophie [1 ]
Gandon, Vincent [1 ]
机构
[1] Univ Paris 11, LabEx CHARMMMAT, ICMMO, UMR CNRS 8182, F-91405 Orsay, France
关键词
catalysis; copper; cyclization; gold; hydroalkylation; HOMOGENEOUS GOLD CATALYSIS; UNACTIVATED ALKENES; MECHANISTIC INSIGHTS; CYCLOISOMERIZATION; COMPLEXES; HYDRATION; PLATINUM; ALCOHOLS; LIGANDS;
D O I
10.1002/anie.201300600
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The right combination: CuI and CuII salts can advantageously replace silver additives in AuI-catalyzed reactions. On the basis of reactivity studies and NMR experiments, it is believed that anion metathesis between CuYn (Y=OTf, BF4, PF6, SbF6) and [R3PAuCl] takes place to give [R 3PAu]Y. As this process is slow, there is no fast decay of the active species, thus allowing large-scale reactions, even at high temperatures, with low loadings of the gold complex. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:5848 / 5852
页数:5
相关论文
共 46 条
  • [1] [Anonymous], 2008, ANGEW CHEM, V120, P8010
  • [2] [Anonymous], 2004, ANGEW CHEM, DOI DOI 10.1002/ANGE.200460232
  • [3] Gold(I)/Zn(II) catalyzed tandem hydroamination/annulation reaction of 4-yne-nitriles
    Demir, Ayhan S.
    Emrullahoglu, Mustafa
    Buran, Kerem
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (42) : 8032 - 8034
  • [4] Copper/Silver-Cocatalyzed Conia-Ene Reactions of 2-Alkynic 1,3-Dicarbonyl Compounds
    Deng, Chen-Liang
    Zou, Tao
    Wang, Zhi-Qiang
    Song, Ren-Jie
    Li, Jin-Heng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (01) : 412 - 414
  • [5] N-Heterocyclic Carbenes in Late Transition Metal Catalysis
    Diez-Gonzalez, Silvia
    Marion, Nicolas
    Nolan, Steven P.
    [J]. CHEMICAL REVIEWS, 2009, 109 (08) : 3612 - 3676
  • [6] Mo-Au combo catalysis for rapid 1,3-rearrangement of propargyl alcohols into α,β-unsaturated carbonyl compounds
    Egi, Masahiro
    Yamaguchi, Yoshiko
    Fujiwara, Noboru
    Akai, Shuji
    [J]. ORGANIC LETTERS, 2008, 10 (09) : 1867 - 1870
  • [7] Synthesis of (-)-Cubebol by Face-Selective Platinum-, Gold-, or Copper-Catalyzed Cycloisomerization: Evidence of Chirality Transfer and Mechanistic Insights
    Fehr, Charles
    Winter, Beat
    Magpantay, Iris
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (38) : 9773 - 9784
  • [8] Gold and platinum catalysis-a convenient tool for generating molecular complexity
    Fuerstner, Alois
    [J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) : 3208 - 3221
  • [9] Relativistic effects in homogeneous gold catalysis
    Gorin, David J.
    Toste, F. Dean
    [J]. NATURE, 2007, 446 (7134) : 395 - 403
  • [10] Hashmi A.S. K., 2010, ANGEW CHEM, V122, P5360, DOI DOI 10.1002/ANGE.200907078