Investigating N-methoxy-N′-aryl ureas in oxidative C-H olefination reactions: an unexpected oxidation behaviour

被引：62
作者：
Willwacher, Jens [1 ]
Rakshit, Souvik [2 ]
Glorius, Frank [1 ]
机构：
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
[2] Columbia Univ, Dept Chem, New York, NY 10027 USA
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 13期
关键词：
BOND FORMATION; PD(II)-CATALYZED OLEFINATION; BENZOIC-ACIDS; ACTIVATION; MECHANISM; DERIVATIVES; ALKYNES; ARENES; FUNCTIONALIZATION; REACTIVITY;
D O I：
10.1039/c1ob05636k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report a urea derived directing group for mild and highly selective oxidative C-H bond olefination. Subsequent intramolecular Michael addition affords dihydroquinazolinones in good yields. The N-O bond of the urea substrate exhibits superior oxidative behaviour compared to a variety of other external oxidants.
引用
收藏
页码：4736 / 4740
页数：5
相关论文
共 69 条
[1]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[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]   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
[4]  
[Anonymous], METAL CATALYZED CROS
[5]  
[Anonymous], MIZOROKIHECK REACTIO
[6]   Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].
Boele, MDK ;
van Strijdonck, GPF ;
de Vries, AHM ;
Kamer, PCJ ;
de Vries, JG ;
van Leeuwen, PWNM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1586-1587
[7]   Indirect ortho functionalization of substituted toluenes through ortho olefination of N,N-dimethylbenzylamines tuned by the acidity of reaction conditions [J].
Cai, Guixin ;
Fu, Ye ;
Li, Yizhou ;
Wan, Xiaobing ;
Shi, Zhangjie .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) :7666-7673
[8]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[9]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655
[10]   Computational study of the mechanism of cyclometalation by palladium acetate [J].
Davies, DL ;
Donald, SMA ;
Macgregor, SA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (40) :13754-13755
1234567