Electrochemical Synthesis of 3‐Bromoimidazo[1,2‐a]pyridines Directly from 2‐Aminopyridines and <i>alpha</i>‐Bromoketones

Jian, Wen-Qian; Wang, Haibin; Du, Ke-Si; Zhong, Weiqiang; Huang, Jing‐Mei

doi:10.1002/celc.201900406

Cited by 19 publications

(9 citation statements)

References 60 publications

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“…In 2019 Huang and co‐workers [41] reported the facile electro‐oxidative synthesis of 3‐bromoimidazo[1,2‐ a ]pyridines (Scheme 30). This methodology directly utilizes α‐halo ketones with 2‐aminopyridines, unlike in Scheme 29, which involves in‐situ generation of α‐halo ketones.…”

Section: Non‐metallic Redox Mediator Merged With Electrosynthesismentioning

confidence: 99%

Electrifying Sustainability on Transition Metal‐Free Modes: An Eco‐Friendly Approach for the Formation of C−N Bonds

2021

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Embracing sustainable green methodologies and techniques in chemical transformations has always been in the limelight to the synthetic community. Electrosynthesis has emerged as a powerful, sustainable synthetic tool for molecular synthesis exploiting inexpensive electricity in place of sacrificial chemical oxidizing/reducing reagents. Herein, recent advances in the incorporation of transition metal‐free redox mediators in electrosynthesis for the construction of C−N bonds are outlined. Furthermore, conjugation of this strategy with flow catalysis allows easy scale up of the synthesis of molecular assembly. This comprehensive Review provides an overview of metal‐free mediated electro‐construction of C−N bonds, focusing on the reaction mechanisms involved and its synthetic applications.

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Section: Non‐metallic Redox Mediator Merged With Electrosynthesismentioning

confidence: 99%

Electrifying Sustainability on Transition Metal‐Free Modes: An Eco‐Friendly Approach for the Formation of C−N Bonds

2021

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“…In 2019 Jian and co‐workers reported an effective, facile electrochemical synthesis of 3‐bromoimidazo[1,2‐ a ]pyridines 84 (Scheme ). Starting directly from 2‐aminopyridines 82 and α‐bromoketones 83 , a variety of target compounds 74 were obtained in good yields.…”

Section: Non‐metal‐catalyzed Electrosynthesis Reactionsmentioning

confidence: 99%

Catalytic Electrosynthesis of N,O‐Heterocycles – Recent Advances

Listratova

Voskressensky

2020

Eur J Org Chem

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“…Electrosynthesis is an excellent way of minimizing energy consumption and can also be used successfully for the in situ production of hazardous and unstable reagents, in addition to maximizing energy efficiency. Different electrosynthetic methods have been used, such as by direct oxidation or reduction of substrates, indirect electrolysis (mediated or catalyzed), − or electrogenerated bases such as CH 3 CN, − DMSO, or DMF . The process of paired electrosynthesis has been known for a long time as a convenient and practical methodology, the appellation of which has been to describe electrochemical processes in which both the reaction at the anode and the reaction at the cathode contribute usefully to the formation of the product(s).…”

Section: Introductionmentioning

confidence: 99%

Green Chemistry: Electrochemical Organic Transformations via Paired Electrolysis

Sbei

Hardwick

Ahmed

2021

ACS Sustainable Chem. Eng.

118

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Paired electrolysis is highly valuable from the viewpoint of efficiency as well as atom and energy economies. In order to optimize the latter two for chemical reactions, the development of paired electrochemical processes is necessary. When both of the electrodes in an electrochemical cell (divided and undivided) are applied as working electrodes, and both sides of the processes (oxidation and reduction) yield valuable compounds, this ideal electrolysis phenomena is defined as paired electrosynthesis. This paired electrolysis offers the opportunity to reduce the spent energy and time, when compared with a single electrolysis system that is only used to achieve a product of interest, while ignoring the other side of the electrolysis (anodic or cathodic). In an ideal case, 200% current efficiency could be achieved during paired electrosynthesis using cathodic and anodic processes to provide the same product. Paired electrosynthesis is a highly efficient green process and, therefore, is beneficial for preserving resources and minimizing waste. However, while a paired electrosynthesis is beneficial, both oxidation and reduction processes must be compatible to counter the yield losses and equally ease separation and purification of both sides of the electrode products. Greater efforts are required to perform paired electrosynthesis with a more systematic and rational approach to achieve optimal products under paired conditions. Nevertheless, new computational tools could be applied for assistance in this matter. There is a considerable level of adventure in designing new paired electrosynthetic processes and accompanying opportunities to design innovative and powerful synthetic strategies. Herein, an overview of several examples of paired electrosyntheses and their advantages are summarized that will aid researchers to both develop a greater understanding of this subject and subsequently employ paired electrolysis for green and sustainable synthesis of organic molecules.

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Electrochemical Synthesis of 3‐Bromoimidazo[1,2‐a]pyridines Directly from 2‐Aminopyridines and alpha‐Bromoketones

Cited by 19 publications

References 60 publications

Electrifying Sustainability on Transition Metal‐Free Modes: An Eco‐Friendly Approach for the Formation of C−N Bonds

Electrifying Sustainability on Transition Metal‐Free Modes: An Eco‐Friendly Approach for the Formation of C−N Bonds

Catalytic Electrosynthesis of N,O‐Heterocycles – Recent Advances

Green Chemistry: Electrochemical Organic Transformations via Paired Electrolysis

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