Homogeneous gold-catalyzed efficient oxidative dimerization of propargylic acetates

被引:66
作者
Cui, Li [1 ]
Zhang, Guozhu [1 ]
Zhang, Liming [1 ]
机构
[1] Univ Nevada, Dept Chem, Reno, NV 89557 USA
基金
美国国家科学基金会;
关键词
Catalysis; Oxidation; Dimerization; Homogeneity; Gold; HIGHLY EFFICIENT; GOLD(III); CYCLIZATION; KETONES; ENYNES; CYCLOISOMERIZATION; REARRANGEMENTS; HYDROGENATION; PHOSPHATYLOXY; COMPLEXES;
D O I
10.1016/j.bmcl.2009.03.127
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A highly efficient gold-catalyzed oxidative dimerization of propargylic acetates is developed. In this chemistry, Selectfluor oxidation of Au(I) to Au(III) is readily incorporated into Au-catalyzed tandem reactions of propargylic acetates, and transmetallation and reductive elimination on Au(III) intermediates are likely involved. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3884 / 3887
页数:4
相关论文
共 37 条
  • [1] Alternative synthetic methods through new developments in catalysis by gold
    Arcadi, Antonio
    [J]. CHEMICAL REVIEWS, 2008, 108 (08) : 3266 - 3325
  • [2] Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones
    Buzas, Andrea
    Gagosz, Fabien
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12614 - 12615
  • [3] Tandem PtCl2 catalyzed-thermal [3,3] rearrangements of enyne acetates
    Cariou, K
    Mainetti, E
    Fensterbank, L
    Malacria, M
    [J]. TETRAHEDRON, 2004, 60 (43) : 9745 - 9755
  • [4] Supported gold catalyzes the homocoupling of phenylboronic acid with high conversion and selectivity
    Carrettin, S
    Guzman, J
    Corma, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (15) : 2242 - 2245
  • [5] Reactions of gold(III) oxo complexes with cyclic alkenes
    Cinellu, MA
    Minghetti, G
    Cocco, T
    Stoccoro, S
    Zucca, A
    Manassero, M
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (42) : 6892 - 6895
  • [6] Single-site homogeneous and heterogenized gold(III) hydrogenation catalysts:: Mechanistic implications
    Comas-Vives, A
    González-Arellano, C
    Corma, A
    Iglesias, M
    Sánchez, F
    Ujaque, G
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (14) : 4756 - 4765
  • [7] Catalytic carbophilic activation:: Catalysis by platinum and gold π acids
    Fuerstner, Alois
    Davies, Paul W.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (19) : 3410 - 3449
  • [8] Gold (I) and (III) catalyze Suzuki cross-coupling and homocoupling, respectively
    González-Arellano, C
    Corma, A
    Iglesias, M
    Sánchez, F
    [J]. JOURNAL OF CATALYSIS, 2006, 238 (02) : 497 - 501
  • [9] Enantioselective hydrogenation of alkenes and imines by a gold catalyst
    González-Arellano, C
    Corma, A
    Iglesias, M
    Sánchez, F
    [J]. CHEMICAL COMMUNICATIONS, 2005, (27) : 3451 - 3453
  • [10] Ligand effects in homogeneous Au catalysis
    Gorin, David J.
    Sherry, Benjamin D.
    Toste, F. Dean
    [J]. CHEMICAL REVIEWS, 2008, 108 (08) : 3351 - 3378