Ligand promoted Pd-catalyzed dehydrogenative alkenylation of hetereoarenes

被引:38
作者
Lee, Wei-Chih [1 ]
Wang, Ting-Hsuan [1 ,2 ,3 ]
Ong, Tiow-Gan [1 ]
机构
[1] Acad Sinica, Inst Chem, Taipei, Taiwan
[2] Natl Tsing Hua Univ, Dept Engn & Syst Sci, Hshichu, Taiwan
[3] Acad Sinica, Taiwan Int Grad Program, Nano Sci & Technol Program, Taipei 115, Taiwan
关键词
H BOND ACTIVATION; CARBON-HYDROGEN BONDS; DIRECT ARYLATION; AROMATIC SUBSTITUTION; C3; ALKENYLATION; N-OXIDES; PALLADIUM; FUNCTIONALIZATION; METAL; BENZOXAZOLES;
D O I
10.1039/c3cc48750d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient Pd-catalyzed cross-dehydrogenative coupling of heteroarenes with styrenes and other olefinic substrates has been developed. This alkenylation paradigm encompasses a wide range of substrates and provides a straightforward approach toward C2-E-alkenylated azole motifs.
引用
收藏
页码:3671 / 3673
页数:3
相关论文
共 62 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]   A domino copper-catalyzed C-N and C-O cross-coupling for the conversion of primary amides into benzoxazoles [J].
Altenhoff, G ;
Glorius, F .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1661-1664
[4]   Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: Regioselective and switchable C-H alkenylation and annulation of pyrroles [J].
Beck, EM ;
Grimster, NP ;
Hatley, R ;
Gaunt, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2528-2529
[5]   Stereoselective direct copper-catalyzed alkenylation of oxazoles with bromoalkenes [J].
Besselievre, Francois ;
Piguel, Sandrine ;
Mahuteau-Betzer, Florence ;
Grierson, David S. .
ORGANIC LETTERS, 2008, 10 (18) :4029-4032
[6]   C-H Bond Activation: A Versatile Protocol for the Direct Arylation and Alkenylation of Oxazoles [J].
Besselievre, Francois ;
Lebrequier, Sabrina ;
Mahuteau-Betzer, Florence ;
Piguel, Sandrine .
SYNTHESIS-STUTTGART, 2009, (20) :3511-3518
[7]   Directed palladation: fine tuning permits the catalytic 2-alkenylation of indoles [J].
Capito, E ;
Brown, JM ;
Ricci, A .
CHEMICAL COMMUNICATIONS, 2005, (14) :1854-1856
[8]   Palladium-Catalyzed Intermolecular C3 Alkenylation of Indoles Using Oxygen as the Oxidant [J].
Chen, Wen-Liang ;
Gao, Ya-Ru ;
Mao, Shuai ;
Zhang, Yan-Lei ;
Wang, Yu-Fei ;
Wang, Yong-Qiang .
ORGANIC LETTERS, 2012, 14 (23) :5920-5923
[9]   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
[10]   Efficient Aerobic Oxidative Synthesis of 2-Substituted Benzoxazoles, Benzothiazoles, and Benzimidazoles Catalyzed by 4-Methoxy-TEMPO [J].
Chen, Yong-Xing ;
Qian, Ling-Feng ;
Zhang, Wei ;
Han, Bing .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (48) :9330-9333