Palladium-Catalyzed Oxidative Carbonylation of Benzylic C-H Bonds via Nondirected C(sp3)-H Activation

被引:246
作者
Xie, Pan [1 ]
Xie, Yinjun [1 ]
Qian, Bo [1 ]
Zhou, Han [1 ]
Xia, Chungu [1 ]
Huang, Hanmin [1 ]
机构
[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
CARBON-HYDROGEN BONDS; PHENYLACETIC ACIDS; AROMATIC-COMPOUNDS; COUPLING REACTIONS; ARYL; CARBOXYLATION; AMINATION; MONOXIDE; HALIDES; HYDROCARBONS;
D O I
10.1021/ja3036459
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new strategy for generating benzylpalladium reactive species from toluenes via nondirected C(sp(3))-H activation has been developed. This led to construction of an efficient Pd-catalyzed reaction protocol for the oxidative carboxylation of benzylic C-H bonds to form substituted 2-phenylacetic acid esters and derivatives from inexpensive, commercially available starting materials.
引用
收藏
页码:9902 / 9905
页数:4
相关论文
共 57 条
[31]   Palladium-catalyzed carbonylation of benzyl chlorides to phenylacetic acids - A new two-phase process [J].
Kohlpainter, CW ;
Beller, M .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 116 (1-2) :259-267
[32]  
Kollar L.A., 2008, Modern Carbonylation Methods
[33]  
Lednicer D., 1980, ORGANIC CHEM DRUG SY, V2, P62
[34]   Direct functionalization of nitrogen heterocycles via Rh-catalyzed C-H bond activation [J].
Lewis, Jared C. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (08) :1013-1025
[35]   Toward a synthetically useful stereoselective C-H amination of hydrocarbons [J].
Liang, Chungen ;
Collet, Florence ;
Robert-Peillard, Fabien ;
Mueller, Paul ;
Dodd, Robert H. ;
Dauban, Philippe .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (01) :343-350
[36]   Oxidative Carbonylation Reactions: Organometallic Compounds (R-M) or Hydrocarbons (R-H) as Nucleophiles [J].
Liu, Qiang ;
Zhang, Hua ;
Lei, Aiwen .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (46) :10788-10799
[37]   Palladium(II)-catalyzed carboxylation of benzene and other aromatic compounds with carbon monoxide under very mild conditions [J].
Lu, WJ ;
Yamaoka, Y ;
Taniguchi, Y ;
Kitamura, T ;
Takaki, K ;
Fujiwara, Y .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 580 (02) :290-294
[38]   Hydroxyl-directed C-H carbonylation enabled by mono-N-protected amino acid ligands: An expedient route to 1-isochromanones [J].
Lu, Yi ;
Leow, Dasheng ;
Wang, Xisheng ;
Engle, Keary M. ;
Yu, Jin-Quan .
CHEMICAL SCIENCE, 2011, 2 (05) :967-971
[39]   Palladium-Catalyzed Ligand-Directed C-H Functionalization Reactions [J].
Lyons, Thomas W. ;
Sanford, Melanie S. .
CHEMICAL REVIEWS, 2010, 110 (02) :1147-1169
[40]   Synthesis of Quinazolin-4(3H)-ones via Pd(II)-Catalyzed Intramolecular C(sp2)-H Carboxamidation of N-arylamidines [J].
Ma, Bin ;
Wang, Yong ;
Peng, Jiangling ;
Zhu, Qiang .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (15) :6362-6366