Palladium- Catalyzed Intermolecular C-2 Alkenylation of Indoles Using Oxygen as the Oxidant

被引:44
作者
Yan, Zhao-Lei [1 ]
Chen, Wen-Liang [1 ]
Gao, Ya-Ru [1 ]
Mao, Shuai [1 ]
Zhang, Yan-Lei [1 ]
Wang, Yong-Qiang [1 ]
机构
[1] NW Univ Xian, Minist Educ, Dept Chem & Mat Sci, Key Lab Synthet & Nat Funct Mol Chem, Xian 710069, Peoples R China
基金
中国国家自然科学基金;
关键词
C-2; alkenylation; CH activation; indoles; oxygen oxidation; palladium-catalyzed reaction; H BOND FUNCTIONALIZATION; BIOLOGICAL EVALUATION; OLEFINATION; C2-ALKENYLATION; ALKALOIDS; HETEROCYCLES; ARENES; MILD;
D O I
10.1002/adsc.201300811
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A general and efficient palladium-catalyzed intermolecular direct C-2 alkenylation of indoles using oxygen as the oxidant has been developed. The reaction is of complete regio- and stereoselectivity. All products are E-isomers at the C-2-position with no Z-isomers and 3-substituted products were detected.
引用
收藏
页码:1085 / 1092
页数:8
相关论文
共 43 条
[1]   Ruthenium-Catalyzed Oxidative C-H Alkenylations of Anilides and Benzamides in Water [J].
Ackermann, Lutz ;
Wang, Lianhui ;
Wolfram, Ratnakancana ;
Lygin, Alexander V. .
ORGANIC LETTERS, 2012, 14 (03) :728-731
[2]  
Bandini M., 2009, ANGEW CHEM, V121, P9786, DOI DOI 10.1002/ange.200901843
[3]   Catalytic Functionalization of Indoles in a New Dimension [J].
Bandini, Marco ;
Eichholzer, Astrid .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644
[4]   Synthesis and biological evaluation of a class of 5-benzylidene-2-phenyl-thiazolinones as potent 5-lipoxygenase inhibitors [J].
Barzen, Sebastian ;
Roedl, Carmen B. ;
Lill, Andreas ;
Steinhilber, Dieter ;
Stark, Holger ;
Hofmann, Bettina .
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (11) :3575-3583
[5]  
Beck E.M., 2008, ANGEW CHEM INT EDIT, V120, P3046
[6]   Synthesis of rhazinicine by a metal-catalyzed C-H bond functionalization strategy [J].
Beck, Elizabeth M. ;
Hatley, Richard ;
Gaunt, Matthew J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (16) :3004-3007
[7]   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
[8]   Overcoming the "Oxidant Problem": Strategies to Use O2 as the Oxidant in Organometallic C-H Oxidation Reactions Catalyzed by Pd (and Cu) [J].
Campbell, Alison N. ;
Stahl, Shannon S. .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :851-863
[9]   Directed palladation: fine tuning permits the catalytic 2-alkenylation of indoles [J].
Capito, E ;
Brown, JM ;
Ricci, A .
CHEMICAL COMMUNICATIONS, 2005, (14) :1854-1856
[10]   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