Palladium-Catalyzed Cross-Coupling of Internal Alkenes with Terminal Alkenes to Functionalized 1,3-Butadienes Using C-H Bond Activation: Efficient Synthesis of Bicyclic Pyridones

被引:168
作者
Yu, Haifeng [1 ,2 ]
Jin, Weiwei [1 ]
Sun, Chenglin [1 ]
Chen, Jiping [1 ]
Du, Wangmin [1 ]
He, Songbo [1 ]
Yu, Zhengkun [1 ,3 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[2] Anshan Normal Univ, Dept Chem, Anshan 114007, Liaoning, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国博士后科学基金;
关键词
alkenes; alkenylation; C-H activation; heterocycles; palladium; PD(II)-CATALYZED OLEFINATION; DIRECT ALKENYLATION; DIRECT ARYLATION; REACTIVITY; ACRYLATES; INDOLES;
D O I
10.1002/anie.201002737
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
chemical equation presented A highly regioselective direct cross-coupling of internal alkenes of a-oxoketene dithioacetals with terminal alkenes has been successfully realized by palladiumcatalyzed C-H bond activation, affording functionalized 1,3-butadienes. Condensation of the resultant 1,3-butadienes by diamines efficiently produced potentially bioactive bicyclic pyridone derivatives (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:5792 / 5797
页数:6
相关论文
共 44 条
[1]  
Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996
[2]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[3]  
[Anonymous], 2009, ANGEW
[4]  
[Anonymous], 2010, Angew. Chem. Int. Ed
[5]  
[Anonymous], 2009, ANGEW CHEM
[6]  
[Anonymous], 2010, ANGEW CHEM
[7]  
[Anonymous], 2009, ANGEW CHEM
[8]   Silver-catalyzed direct couplings of 2-substituted furans with cyclic 1,3-dicarbonyls [J].
Arcadi, Antonio ;
Alfonsi, Maria ;
Marinelli, Fabio .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (23) :5322-5326
[9]   Ruthenium-Catalyzed Synthesis of Functionalized Dienes from Propargylic Esters: Formal Cross-Coupling of Two Carbenes [J].
Bray, Chloe Vovard-Le ;
Derien, Sylvie ;
Dixneuf, Pierre H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (08) :1439-1442
[10]  
Chen X., 2009, ANGEW CHEM, V121, P5196