Microwave-Assisted Decarboxylative Three-Component Coupling of a 2-Oxoacetic Acid, an Amine, and an Alkyne

被引:51
作者
Feng, Huangdi [1 ,2 ]
Ermolat'ev, Denis S. [1 ]
Song, Gonghua [2 ]
Van der Eycken, Erik V. [1 ]
机构
[1] Katholieke Univ Leuven, Dept Chem, LOMAC, B-3001 Heverlee, Belgium
[2] E China Univ Sci & Technol, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China
关键词
TERMINAL ALKYNES; DIASTEREOSELECTIVE SYNTHESIS; CARBOXYLIC-ACIDS; DIRECT ADDITION; PROPARGYLAMINES; ALDEHYDE; GOLD; ACCESS; ACYLATION; CATALYSTS;
D O I
10.1021/jo2013725
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and efficient microwave-assisted decarboxylative three-component coupling of a 2-oxoacetic acid, an amine, and an alkyne (OA(2)-coulpling) has been developed. This new multicomponent coupling constitutes an efficient approach for the synthesis of polysubstituted propargylamines in the presence of a catalytic amount of copper(I) catalyst.
引用
收藏
页码:7608 / 7613
页数:6
相关论文
共 59 条
[1]   Gold-Nanoparticle-Catalyzed Synthesis of Propargylamines: The Traditional A3-Multicomponent Reaction Performed as a Two-Step Flow Process [J].
Abahmane, Lahbib ;
Koehler, J. Michael ;
Gross, G. Alexander .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (10) :3005-3010
[2]   Mechanistic Insights into the One-Pot Synthesis of Propargylamines from Terminal Alkynes and Amines in Chlorinated Solvents Catalyzed by Gold Compounds and Nanoparticles [J].
Aguilar, David ;
Contel, Maria ;
Urriolabeitia, Esteban P. .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (30) :9287-9296
[3]  
[Anonymous], 2009, ANGEW CHEM
[4]  
[Anonymous], ORGANOMAGNESIUM METH
[5]  
[Anonymous], 2009, ANGEW CHEM-GER EDIT
[6]   Highly enantioselective access to primary propargylamines: 4-piperidinone as a convenient protecting group [J].
Aschwanden, Patrick ;
Stephenson, Corey R. J. ;
Carreira, Erick M. .
ORGANIC LETTERS, 2006, 8 (11) :2437-2440
[7]   Efficient Microwave-Assisted Synthesis of Secondary Alkylpropargylamines by Using A3-Coupling with Primary Aliphatic Amines [J].
Bariwal, Jitender B. ;
Ermolat'ev, Denis S. ;
Van der Eyeken, Erik V. .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (11) :3281-3284
[8]   Synthesis of biaryls via decarboxylative Pd-catalyzed cross-coupling reaction [J].
Becht, Jean-Michel ;
Catala, Cedric ;
Le Drian, Claude ;
Wagner, Alain .
ORGANIC LETTERS, 2007, 9 (09) :1781-1783
[9]   The Copper-Catalyzed Decarboxylative Coupling of the sp3-Hybridized Carbon Atoms of α-Amino Acids [J].
Bi, Hai-Peng ;
Zhao, Liang ;
Liang, Yong-Min ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (04) :792-795
[10]   Palladium-Catalyzed Decarboxylative Cross-Coupling Reaction Between Heteroaromatic Carboxylic Acids and Aryl Halides [J].
Bilodeau, Francois ;
Brochu, Marie-Christine ;
Guimond, Nicolas ;
Thesen, Kris H. ;
Forgione, Pat .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05) :1550-1560