Rapid Access to Chroman-3-ones through Gold-Catalyzed Oxidation of Propargyl Aryl Ethers

被引:130
作者
Wang, Yanzhao [1 ]
Ji, Kegong [1 ]
Lan, Sylvester [1 ]
Zhang, Liming [1 ]
机构
[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
关键词
carbenes; gold; heterocycles; homogeneous catalysis; oxidation; ALPHA-DIAZO KETONES; EFFICIENT SYNTHESIS; PHOSPHINE; 1,5-ENYNES; COMPLEXES; ALKYNES;
D O I
10.1002/anie.201107561
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The two-step: Chroman-3-ones are important intermediates for organic synthesis and medicinal chemistry. However, their syntheses require multiple steps and are not efficient. By using gold-catalyzed alkyne oxidation, this versatile heterocycle can be prepared in only two steps from readily available phenols and with mostly high efficiencies (see scheme). © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:1915 / 1918
页数:4
相关论文
共 47 条
  • [1] Gold(I)-catalyzed intermolecular addition of carbon nucleophiles to 1,5- and 1,6-enynes
    Amijs, Catelijne H. M.
    Lopez-Carrillo, Veronica
    Raducan, Mihai
    Perez-Galan, Patricia
    Ferrer, Catalina
    Echavarren, Antonio M.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19) : 7721 - 7730
  • [2] [Anonymous], 2011, ANGEW CHE
  • [3] Synthesis of Fused Carbocycles via a Selective 6-Endo Dig Gold(I)-Catalyzed Carbocyclization
    Barabe, Francis
    Levesque, Patrick
    Korobkov, Ilia
    Barriault, Louis
    [J]. ORGANIC LETTERS, 2011, 13 (20) : 5580 - 5583
  • [4] Burgos C. H., 2006, ANGEW CHEM, V118, P4427
  • [5] Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects
    Burgos, Carlos H.
    Barder, Timothy E.
    Huang, Xiaohua
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) : 4321 - 4326
  • [6] Percent buried volume for phosphine and N-heterocyclic carbene ligands: steric properties in organometallic chemistry
    Clavier, Herve
    Nolan, Steven P.
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (06) : 841 - 861
  • [7] ENANTIOSELECTIVE TOTAL SYNTHESIS OF MIROESTROL
    COREY, EJ
    WU, LI
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (20) : 9327 - 9328
  • [8] DANAN A, 1991, B SOC CHIM FR, P189
  • [9] Site-specific introduction of gold-carbenoids by intermolecular oxidation of ynamides or ynol ethers
    Davies, Paul W.
    Cremonesi, Alex
    Martin, Nicolas
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (01) : 379 - 381
  • [10] Dorwald F.Z., 1999, METAL CARBENES ORGAN