Carbon-Carbon Bond Formation: Palladium-Catalyzed Oxidative Cross-Coupling of N-Tosylhydrazones with Allylic Alcohols

被引:44
作者
Chen, Huoji [1 ]
Huang, Li [1 ]
Fu, Wei [1 ]
Liu, Xiaohang [1 ]
Jiang, Huanfeng [1 ]
机构
[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
allylic compounds; C?C coupling; cross-coupling; N-tosylhydrazones; palladium; ALPHA-DIAZOCARBONYL COMPOUNDS; MIGRATORY INSERTION; ARYL HALIDES; CARBENE COMPLEXES; BENZYL BROMIDES; DIAZOESTERS; ARYLATION; REAGENTS; OLEFINS; ESTERS;
D O I
10.1002/chem.201200949
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the zone: Pd-catalyzed oxidative cross-coupling of N-tosylhydrazones with allylic alcohols leads to C-C bond formation. A palladium-carbene migratory insertion is proposed to play the key role in this transformation. The reaction proceeds with readily available starting materials to afford substituted alkenes in a highly stereoselective manner (see scheme). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:10497 / 10500
页数:4
相关论文
共 54 条
[1]   Formation of a vinyliminium palladium complex by C-C coupling in vinylcarbene palladium aryl complexes [J].
Albéniz, AC ;
Espinet, P ;
Pérez-Mateo, A ;
Nova, A ;
Ujaque, G .
ORGANOMETALLICS, 2006, 25 (05) :1293-1297
[2]   Aryl palladium carbene complexes and carbene-aryl coupling reactions [J].
Albéniz, AC ;
Espinet, P ;
Manrique, R ;
Pérez-Mateo, A .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (05) :1565-1573
[3]  
Albéniz AC, 2002, ANGEW CHEM INT EDIT, V41, P2363, DOI 10.1002/1521-3773(20020703)41:13<2363::AID-ANIE2363>3.0.CO
[4]  
2-9
[5]  
ALBENIZ AC, 2002, ANGEW CHEM, V114, P2469
[6]  
[Anonymous], 2011, ANGEW CHEM
[7]  
[Anonymous], 2012, Angew. Chem. Int. Ed, DOI DOI 10.1002/ANGE.201106619
[8]  
[Anonymous], 2009, ANGEW CHE
[9]  
Barluenga J, 2010, ANGEW CHEM, V122, P7008
[10]  
Barluenga J., 2007, Angew. Chem, V119, P5683