Gold-Catalyzed Intermolecular Oxidation of Terminal Alkynes: Simple and Efficient Synthesis of α-Mesyloxy Ketones

被引:28
作者
Xie, Longyong [1 ]
Liang, Zhiwu [1 ]
Yan, Dong [1 ,2 ]
He, Weimin [1 ]
Xiang, Jiannan [1 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Hunan, Peoples R China
[2] Hunan Chem Ind Vocat Technol Inst, Zhuzhou 412004, Peoples R China
基金
湖南省自然科学基金;
关键词
alkynes; homogenous catalysis; gold; alpha-oxo gold carbine; alpha-mesyloxy ketones; ONE-POT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; PHOTOCHEMICAL-SYNTHESIS; REARRANGEMENT; HETEROCYCLES; YLIDES; ACCESS; ROUTE; CYCLOPROPANATION; CYCLOADDITION;
D O I
10.1055/s-0033-1339337
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of terminal alkynes were efficiently converted into the corresponding alpha-mesyloxy ketones through gold-catalyzed intermolecular oxidation in the presence of 3,5-dichloropyridine N-oxide as the oxidant. The reaction is proposed to proceed via alpha-oxo gold carbene intermolecular O-H insertion.
引用
收藏
页码:1809 / 1812
页数:4
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    Liu, Yuanhong
    [J]. ORGANIC LETTERS, 2007, 9 (21) : 4323 - 4326
  • [52] A Flexible and Stereoselective Synthesis of Azetidin-3-ones through Gold-Catalyzed Intermolecular Oxidation of Alkynes
    Ye, Longwu
    He, Weimin
    Zhang, Liming
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (14) : 3236 - 3239
  • [53] Gold-Catalyzed One-Step Practical Synthesis of Oxetan-3-ones from Readily Available Propargylic Alcohols
    Ye, Longwu
    He, Weimin
    Zhang, Liming
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (25) : 8550 - +
  • [54] Alkynes as Equivalents of α-Diazo Ketones in Generating α-Oxo Metal Carbenes: A Gold-Catalyzed Expedient Synthesis of Dihydrofuran-3-ones
    Ye, Longwu
    Cui, Li
    Zhang, Guozhu
    Zhang, Liming
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (10) : 3258 - +
  • [55] Gold-catalyzed waste-free generation and reaction of azomethine ylides: Internal redox/dipolar cycloaddition cascade
    Yeom, Hyttn-Suk
    Lee, Ji-Eun
    Shin, Setinghoon
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (37) : 7040 - 7043
  • [56] Au(I)-catalyzed intramolecular oxidative cyclopropanation of 1,6-enynes derived from propiolamides with diphenyl sulfoxide
    Yeom, Hyun-Suk
    Shin, Seunghoon
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (07) : 1089 - 1092
  • [57] Stereoselective One-Pot Synthesis of 1-Aminoindanes and 5,6 Fused Azacycles Using a Gold-Catalyzed Redox-Pinacol-Mannich-Michael Cascade
    Yeom, Hyun-Suk
    Lee, Youngun
    Jeong, Jaewon
    So, Eunsoo
    Hwang, Soojin
    Lee, Ji-Eun
    Lee, Shim Sung
    Shin, Seunghoon
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (09) : 1611 - 1614