Palladium-catalyzed oxidative C-H/C-H cross-coupling of benzothiazoles with thiophenes and thiazoles

被引:47
作者
Chen, Xuxing [1 ]
Huang, Xiaojing [1 ]
He, Qian [1 ]
Xie, Yuyuan [1 ]
Yang, Chunhao [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
关键词
SILVER CENTERS; PD CATALYSTS; HETEROARENES; ARYLATION; PYRIDINES; DERIVATIVES; ACTIVATION; AZOLES; BONDS; ALKYL;
D O I
10.1039/c4cc00362d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A concise palladium-catalyzed method for oxidative C-H/C-H cross-coupling between benzothiazoles and thiophenes/thiazoles has been developed. This CDC reaction is insensitive to air and moisture with high functional group tolerance.
引用
收藏
页码:3996 / 3999
页数:4
相关论文
共 42 条
[1]   Reactivity of [NBU4][(C6F5)2M(μ-PPh2)2M′(acac-O,O′)] (M, M′ = Pt, Pd) toward silver centers.: Synthesis of polynuclear complexes containing M-Ag bonds (M = PdPt) [J].
Alonso, E ;
Forniés, J ;
Fortuño, C ;
Martín, A ;
Orpen, AG .
ORGANOMETALLICS, 2003, 22 (24) :5011-5019
[2]   Two-Photon Fluorescence Vascular Bioimaging with New Bioconjugate Probes Selective toward the Vascular Endothelial Growth Factor Receptor 2 [J].
Andrade, Carolina D. ;
Yanez, Ciceron O. ;
Ahn, Hyo-Yang ;
Urakami, Takeo ;
Bondar, Mykhailo V. ;
Komatsu, Masanobu ;
Belfied, Kevin D. .
BIOCONJUGATE CHEMISTRY, 2011, 22 (10) :2060-2071
[3]   Copper-catalyzed arylation of heterocycle C-H bonds [J].
Do, Hien-Quang ;
Daugulis, Olafs .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (41) :12404-+
[4]   A General Method for Copper-Catalyzed Arene Cross-Dimerization [J].
Do, Hien-Quang ;
Daugulis, Olafs .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (34) :13577-13586
[5]   Palladium(II)-Catalyzed Oxidative C-H/C-H Cross-Coupling between Two Structurally Similar Azoles [J].
Dong, Jiaxing ;
Huang, Yumin ;
Qin, Xurong ;
Cheng, Yangyang ;
Hao, Jing ;
Wan, Danyang ;
Li, Wei ;
Liu, Xingyan ;
You, Jingsong .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (20) :6158-6162
[6]   C-C bond formation via double C-H functionalization: Aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls [J].
Dwight, Timothy A. ;
Rue, Nicholas R. ;
Charyk, Dagmara ;
Josselyn, Ryan ;
DeBoef, Brenton .
ORGANIC LETTERS, 2007, 9 (16) :3137-3139
[7]   Copper-Catalyzed Dehydrogenative Cross-Coupling of Benzothiazoles with Thiazoles and Polyfluoroarene [J].
Fan, Shilu ;
Chen, Zhao ;
Zhang, Xingang .
ORGANIC LETTERS, 2012, 14 (18) :4950-4953
[8]   Behavior of Neutral Phosphido Derivatives of Platinum and Palladium toward Silver Centers [J].
Fornies, Juan ;
Fortuno, Consuelo ;
Ibanez, Susana ;
Martin, Antonio ;
Mastrorilli, Piero ;
Gallo, Vito .
INORGANIC CHEMISTRY, 2011, 50 (21) :10798-10809
[9]   Dual C-H activations of electron-deficient heteroarenes: palladium-catalyzed oxidative cross coupling of thiazoles with azine N-oxides [J].
Fu, Xiao-Pu ;
Xuan, Qing-Qing ;
Liu, Li ;
Wang, Dong ;
Chen, Yong-Jun ;
Li, Chao-Jun .
TETRAHEDRON, 2013, 69 (22) :4436-4444
[10]   Design and Synthesis of 2-Acylbenzothiazoles via In Situ Cross-Trapping Strategy from Benzothiazoles with Aryl Ketones [J].
Gao, Qinghe ;
Wu, Xia ;
Jia, Fengcheng ;
Liu, Meicai ;
Zhu, Yanping ;
Cai, Qun ;
Wu, Anxin .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (06) :2792-2797