Recent Advances in the Synthesis of 2,2′-Bipyridines and Their Derivatives

被引:13
作者
Rubtsov, Aleksandr E. [1 ]
Malkov, Andrei V. [2 ]
机构
[1] Perm State Univ, Dept Chem, Bukireva 15, Perm 614990, Russia
[2] Loughborough Univ, Dept Chem, Loughborough LE11 3TU, Leics, England
来源
SYNTHESIS-STUTTGART | 2021年 / 53卷 / 15期
基金
俄罗斯科学基金会;
关键词
bipyridines; cross-coupling; catalysis; oxidative dimerization; C-H activation; regioselectivity; chemoselectivity; ATROPOISOMERIC BIPYRIDINE N; N'-DIOXIDES; HETEROAROMATIC N-OXIDES; HIGH-YIELDING SYNTHESIS; ENANTIOSELECTIVE ALLYLATION; CHIRAL 2,2'-BIPYRIDINES; ALDOL ADDITION; LIGAND; ARYL; DIMERIZATION; COMPLEXES;
D O I
10.1055/s-0040-1706030
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The sustained interest in the synthesis of new analogues of 2,2'-bipyridines is supported by the importance of compounds featuring bipyridine core in diverse areas of chemical, biomedical and materials research, which is relayed into the development of new approaches and the expansion of existing synthetic methods. This short review covers advances in the synthesis of 2,2'-bipyridines, including both the synthesis of compounds with a given substitution pattern and the development of new methods for assembling the bipyridine core. Special attention is directed toward the use of pyridine N-oxides and metal-free protocols to facilitate the formation of bipyridines. This short review focuses primarily on reports published in the last 5-6 years. 1 Introduction 2 Ullmann-Type Homocoupling Reactions 3 Cross-Coupling Reactions in the Synthesis of Bipyridines 4 Coupling Reactions Employing Pyridine N-Oxides 5 Other Methods for the Synthesis of 2,2 '-Bipyridines 6 Conclusions and Outlook
引用
收藏
页码:2559 / 2569
页数:11
相关论文
共 97 条
[91]   Dehydrogenative Synthesis of 2,2′-Bipyridyls through Regioselective Pyridine Dimerization [J].
Yamada, Shuya ;
Kaneda, Takeshi ;
Steib, Philip ;
Murakami, Kei ;
Itami, Kenichiro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (25) :8341-8345
[92]  
YAMAMOTO Y, 1986, SYNTHESIS-STUTTGART, P564
[93]   Oxidative C-H/C-H Coupling Reactions between Two (Hetero)arenes [J].
Yang, Yudong ;
Lan, Jingbo ;
You, Jingsong .
CHEMICAL REVIEWS, 2017, 117 (13) :8787-8863
[94]   Synthesis of DMF-protected Au NPs with different size distributions and their catalytic performance in the Ullmann homocoupling of aryl iodides [J].
Yao, Wang ;
Gong, Wei-Jie ;
Li, Hong-Xi ;
Li, Fei-Long ;
Gao, Jun ;
Lang, Jian-Ping .
DALTON TRANSACTIONS, 2014, 43 (42) :15752-15759
[95]   Salt- Free Reduction of Nonprecious Transition- Metal Compounds: Generation of Amorphous Ni Nanoparticles for Catalytic C-C Bond Formation [J].
Yurino, Taiga ;
Ueda, Yohei ;
Shimizu, Yoshiki ;
Tanaka, Shinji ;
Nishiyama, Haruka ;
Tsurugi, Hayato ;
Sato, Kazuhiko ;
Mashima, Kazushi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (48) :14437-14441
[96]   Chiral bipyridine-annulated bicyclo[3.3.1]nonane N-oxide organocatalysts for stereoselective allylation and hydrosilylation reactions [J].
Zeimyte, Simona ;
Stoncius, Sigitas .
TETRAHEDRON, 2021, 78
[97]   Palladium-Catalyzed Directed Halogenation of Bipyridine N-Oxides [J].
Zucker, Sina P. ;
Wossidlo, Friedrich ;
Weber, Manuela ;
Lentz, Dieter ;
Tzschucke, C. Christoph .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (11) :5616-5635