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
相关论文
共 57 条
[51]   Gold-catalyzed multicomponent synthesis of aminoindolizines from aldehydes, amines, and Alkynes under solvent-free conditions or in water [J].
Yan, Bin ;
Liu, Yuanhong .
ORGANIC LETTERS, 2007, 9 (21) :4323-4326
[52]   A Flexible and Stereoselective Synthesis of Azetidin-3-ones through Gold-Catalyzed Intermolecular Oxidation of Alkynes [J].
Ye, Longwu ;
He, Weimin ;
Zhang, Liming .
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 [J].
Ye, Longwu ;
He, Weimin ;
Zhang, Liming .
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 [J].
Ye, Longwu ;
Cui, Li ;
Zhang, Guozhu ;
Zhang, Liming .
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 [J].
Yeom, Hyttn-Suk ;
Lee, Ji-Eun ;
Shin, Setinghoon .
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 [J].
Yeom, Hyun-Suk ;
Shin, Seunghoon .
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 [J].
Yeom, Hyun-Suk ;
Lee, Youngun ;
Jeong, Jaewon ;
So, Eunsoo ;
Hwang, Soojin ;
Lee, Ji-Eun ;
Lee, Shim Sung ;
Shin, Seunghoon .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (09) :1611-1614