Synthesis of Enol Ethers and Enamines by Pd-Catalyzed Tosylhydrazide-Promoted Cross-Coupling Reactions

被引:91
作者
Barluenga, Jose [1 ]
Escribano, Maria [1 ]
Moriel, Patricia [1 ]
Aznar, Fernando [1 ]
Valdes, Carlos [1 ]
机构
[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, E-33006 Oviedo, Spain
关键词
cross-coupling; enamines; enol ethers; hydrazones; palladium; CARBENE INSERTION; ALPHA-ARYLATION; BOND FORMATION; ARYL BROMIDES; VINYL HALIDES; PALLADIUM; ALDEHYDES; CLEAVAGE;
D O I
10.1002/chem.200902718
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
"Chemical Equation Presented" α-Substitution is fine: α-Alkoxycarbonyl and α-aminocarbonyl compounds are good substrates for the recently developed tosylhydrazide-promoted Pd-catalyzed cross-coupling of carbonyls with aryl halides. The reac-tion gives rise to enol ethers and enamines, respectively, which are useful synthetic intermediates in heterocyclic synthesis. Otherwise, they can be hydrolyzed to give α,α- disubstituted aldehydes. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:13291 / 13294
页数:4
相关论文
共 31 条
[1]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[2]  
AZNAR F, 2007, ANGEW CHEM, V119, P5683
[3]  
Barluenga J., 2007, Angew. Chem, V119, P5683
[4]   Pd-catalyzed cross-coupling reactions with carbonyls:: Application in a very efficient synthesis of 4-aryltetrahydropyridines [J].
Barluenga, Jose ;
Tomas-Gamasa, Maria ;
Moriel, Patricia ;
Amar, Fernando ;
Valdes, Carlos .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (16) :4792-4795
[5]   N-tosylhydrazones as reagents for cross-coupling reactions:: A route to polysubstituted olefins [J].
Barluenga, José ;
Moriel, Patricia ;
Valdes, Carlos ;
Aznar, Fernando .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5587-5590
[6]  
de Meijere A., 2004, METAL CATALYZED CROS
[7]   Palladium-catalyzed carbene insertion into vinyl halides and trapping with amines [J].
Devine, Sean K. J. ;
Van Vranken, David L. .
ORGANIC LETTERS, 2007, 9 (10) :2047-2049
[8]   Highly active and selective catalysts for the formation of α-aryl ketones [J].
Fox, JM ;
Huang, XH ;
Chieffi, A ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (07) :1360-1370
[9]   Biaryl synthesis via Pd-catalyzed decarboxylative coupling of aromatic carboxylates with aryl halides [J].
Goossen, Lukas J. ;
Rodriguez, Nuria ;
Melzer, Bettina ;
Linder, Christophe ;
Deng, Guojun ;
Levy, Laura M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (15) :4824-4833
[10]   Palladium-catalyzed carbene insertion into benzyl bromides [J].
Greenman, KL ;
Van Vranken, DL .
TETRAHEDRON, 2005, 61 (26) :6438-6441