Palladium-catalyzed three-component synthesis of 3-(diarylmethylene)oxindoles through a domino Sonagashira/carbopalladation/C-H activation/C-C bond-forming sequence

被引:190
作者
Pinto, Artur [1 ]
Neuville, Luc [1 ]
Zhu, Jieping [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
C-H activation; domino reactions; multicomponent reactions; nitrogen heterocycles; palladium;
D O I
10.1002/anie.200605192
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) 3-3-1 Formation: [Pd(PPh3) 4]/Cul serves as an efficient catalyst for the reaction of three readily available starting materials to give 3-(diarylmethylene)indolin-2-ones 3 through a sequence of intermolecular Sonagashira reaction/intermolecular carbopalladation/C-H activation/C-C bond formation (see scheme). Three C-C bonds are thereby formed as a result of three distinct catalytic cycles with one catalyst. DMF = N,N-dimethylformamide. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3291 / 3295
页数:5
相关论文
共 78 条
[31]   Oxindole synthesis through intramolecular nucleophilic addition of vinylpalladiums to aryl isocyanates [J].
Kamijo, S ;
Sasaki, Y ;
Kanazawa, C ;
Schüsseler, T ;
Yamamoto, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (47) :7718-7721
[32]  
Kamijo S., 2005, ANGEW CHEM, V117, P7896
[33]  
Karpov A. S., 2005, ANGEW CHEM, V117, P7112
[34]   Concise syntheses of meridianins by carbonylative alkynylation and a four-component pyrimidine synthesis [J].
Karpov, AS ;
Merkul, E ;
Rominger, F ;
Müller, TJJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (42) :6951-6956
[35]  
Kressierer C. J., 2004, ANGEW CHEM, V116, P6123
[36]   Novel three-component reactions based on a Heck carbopalladation/cyclization domino reaction [J].
Kressierer, CJ ;
Müller, TJJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (44) :5997-6000
[37]   Heck, direct arylation, and hydrogenation:: Two or three sequential reactions from a single catalyst [J].
Leclerc, JP ;
André, M ;
Fagnou, K .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (04) :1711-1714
[38]   Cooperative multi-catalyst systems for one-pot organic transformations [J].
Lee, JM ;
Na, Y ;
Han, H ;
Chang, S .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (05) :302-312
[39]   Quasi-nature catalysis: Developing C-C bond formations catalyzed by late transition metals in air and water [J].
Li, CJ .
ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (07) :533-538
[40]  
Miura M, 2002, TOP CURR CHEM, V219, P211