Palladium-catalyzed alkenation of thiophenes and furans by regioselective C-H bond functionalization

被引:42
作者
Zhao, Jinlong [1 ]
Huang, Lehao [1 ]
Cheng, Kai [1 ]
Zhang, Yuhong [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
关键词
Palladium; Heterocycles; Thiophene; Alkenation; C-H activation; HECK REACTION; ARYL CHLORIDES; OLEFINATION; ARYLATION; ALKENYLATION; ACTIVATION; VINYLATION; ALDEHYDES; BENZENES; LIGANDS;
D O I
10.1016/j.tetlet.2009.03.124
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed direct alkenation of thiophenes and furans has been developed in the presence of AgOAc and pyridine. A variety of olefinic substrates such as acrylates, acrylamides, and acrylonitrile can perform the direct oxidative coupling reactions with various thiophenes and furans to give the mono-alkenylated products in good yields. In most cases, the (E)-isomers were isolated as the major products. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2758 / 2761
页数:4
相关论文
共 45 条
[1]   ARYLATION AND ALKYLATION OF OLEFINS BY ARYLAMINES OR HYDRAZINES VIA CARBON-NITROGEN BOND-CLEAVAGE IN THE PRESENCE OF PALLADIUM(II) SALTS [J].
AKIYAMA, F ;
MIYAZAKI, H ;
KANEDA, K ;
TERANISHI, S ;
FUJIWARA, Y ;
ABE, M ;
TANIGUCHI, H .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (12) :2359-2361
[2]   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
[3]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[4]   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
[5]   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
[6]   Toward waste-free production of Heck products with a catalytic palladium system under oxygen [J].
Dams, M ;
De Vos, DE ;
Celen, S ;
Jacobs, PA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (30) :3512-3515
[7]   The asymmetric intramolecular Heck reaction in natural product total synthesis [J].
Dounay, AB ;
Overman, LE .
CHEMICAL REVIEWS, 2003, 103 (08) :2945-2963
[8]  
Ehrentraut A, 2000, SYNLETT, P1589
[9]   Wittig reactions in water media employing stabilized ylides with aldehydes.: Synthesis of α,β-unsaturated esters from mixing aldehydes, α-bromoesters, and Ph3P in aqueous NaHCO3 [J].
El-Batta, Amer ;
Jiang, Changchun ;
Zhao, Wen ;
Anness, Robert ;
Cooksy, Andrew L. ;
Bergdahl, Mikael .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) :5244-5259
[10]  
FUJIWARA Y, 1976, J ORG CHEM, V41, P1680