One-Pot Synthesis of Symmetrical 2,6-Diarylpyridines via Palladium/Copper-Catalyzed Sequential Decarboxylative and Direct C-H Arylation

被引:16
作者
Ma, Zhiyong [1 ]
Liu, Hailong [1 ]
Zhang, Chunchun [2 ]
Zheng, Xueli [1 ]
Yuan, Maolian [1 ]
Fu, Haiyan [1 ]
Li, Ruixiang [1 ]
Chen, Hua [1 ]
机构
[1] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
[2] Sichuan Univ, Analyt & Testing Ctr, Chengdu 610064, Peoples R China
关键词
C-H functionalization; decarboxylation; 2,6-diarylpyridines; dimethyl sulfate; palladium; CROSS-COUPLING REACTIONS; BOND ARYLATION; PYRIDINES; HETEROCYCLES; COMPLEXES; PALLADATION; OLEFINATION; ALKYLATION; ACETATES; ACIDS;
D O I
10.1002/adsc.201400900
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A palladium(II)/copper oxide (Cu2O)-catalyzed one-pot decarboxylative and direct C-H arylation of 2-picolinic acid with aryl bromides has been developed. Various aryl bromides have been shown to be efficient coupling partners in the presence of dimethyl sulfate, furnishing symmetrical 2,6-diarylpyridines in moderate to good yields.
引用
收藏
页码:1143 / 1148
页数:6
相关论文
共 69 条
[1]   Air-stable PinP(O)H as preligand for palladium-catalyzed Kumada couplings of unactivated tosylates [J].
Ackermann, Lutz ;
Althammer, Andreas .
ORGANIC LETTERS, 2006, 8 (16) :3457-3460
[2]   Direct arylations of electron-deficient (hetero)arenes with aryl or alkenyl tosylates and mesylates [J].
Ackermann, Lutz ;
Fenner, Sabine .
CHEMICAL COMMUNICATIONS, 2011, 47 (01) :430-432
[3]  
[Anonymous], 2010, Angew. Chem. Int. Ed
[4]  
[Anonymous], 2010, ANGEW CHEM
[5]   Rh(I)-Catalyzed Direct Arylation of Pyridines and Quinolines [J].
Berman, Ashley M. ;
Lewis, Jared C. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :14926-+
[6]  
Bhadra S., 2013, ANGEW CHEM, V125, P3031
[7]   Synthesis of Aryl Ethers from Benzoates through Carboxylate-Directed C-H-Activating Alkoxylation with Concomitant Protodecarboxylation [J].
Bhadra, Sukalyan ;
Dzik, Wojciech I. ;
Goossen, Lukas J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (10) :2959-2962
[8]  
Billingsley K.L., 2008, Angew. Chem, V120, P4773
[9]   A general and efficient method for the Suzuki-Miyaura coupling of 2-pyridyl nucleophiles [J].
Billingsley, Kelvin L. ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) :4695-4698
[10]   [Pd(Cl)2{P(NC5H10)(C6H11)2}2]-A Highly Effective and Extremely Versatile Palladium-Based Negishi Catalyst that Efficiently and Reliably Operates at Low Catalyst Loadings [J].
Bolliger, Jeanne L. ;
Frech, Christian M. .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (36) :11072-11081