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

Synthesis ◽  
2021 ◽  
Author(s):  
Aleksandr E. Rubtsov ◽  
Andrei V. Malkov

AbstractThe 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 Introduction2 Ullmann-Type Homocoupling Reactions3 Cross-Coupling Reactions in the Synthesis of Bipyridines4 Coupling Reactions Employing Pyridine N-Oxides5 Other Methods for the Synthesis of 2,2′-Bipyridines6 Conclusions and Outlook

2018 ◽  
Vol 16 (33) ◽  
pp. 6017-6024 ◽  
Author(s):  
Bin Sun ◽  
Shi Yin ◽  
Xiaohui Zhuang ◽  
Can Jin ◽  
Weike Su

We developed a novel metal-free method for the construction of C(sp2)–O bonds via oxidative cross-coupling reactions between various N-substituted anilines and hydroxylamine derivatives just using commercially available Selectfluor as an oxidant.


2018 ◽  
Vol 7 (6) ◽  
pp. 1118-1123 ◽  
Author(s):  
Miao Lai ◽  
Yuan Li ◽  
Zhiyong Wu ◽  
Mingqin Zhao ◽  
Xiaoming Ji ◽  
...  

Synthesis ◽  
2017 ◽  
Vol 49 (15) ◽  
pp. 3269-3280 ◽  
Author(s):  
Tobias Parchomyk ◽  
Konrad Koszinowski

Iron-catalyzed cross-coupling reactions provide a promising way to form new carbon–carbon bonds and build up molecular complexity. This short review presents recent advances in the synthetic application of these reactions as well as in the elucidation of their mechanism. It also highlights remaining problems and aims at pointing out ways toward possible remedies.1 Introduction2 Synthesis: Recent Accomplishments and Unsolved Problems2.1 Substrate Scope: Electrophiles2.2 Substrate Scope: Nucleophiles2.3 Catalyst Activity and Chemoselectivity2.4 Stereoselectivity2.5 Practical Aspects3 Mechanism: Recent Insights and Open Questions3.1 Transmetallation and Activation of the Iron Precatalyst3.2 Coupling via Oxidative Addition and Reductive Elimination3.3 Coupling via C–X Bond Homolysis and Radical Rebound3.4 Coupling via Bimolecular C–X Bond Homolysis3.5 Other Reactions of Organoiron Species with Electrophiles4 Toward Rational Reaction Improvement5 Conclusion


2019 ◽  
Vol 6 (2) ◽  
pp. 152-161 ◽  
Author(s):  
Enrique Barragan ◽  
Anurag Noonikara Poyil ◽  
Chou-Hsun Yang ◽  
Haobin Wang ◽  
Alejandro Bugarin

A metal-free synthesis of biaryl compounds was achieved under photo-irradiation, which represents a milder alternative for cross-coupling reactions.


2014 ◽  
Vol 126 (52) ◽  
pp. 14766-14769 ◽  
Author(s):  
Veronica V. Angeles-Dunham ◽  
David M. Nickerson ◽  
Devin M. Ray ◽  
Anita E. Mattson

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