Electrochemical oxidation synergizing with Brønsted-acid catalysis leads to [4 + 2] annulation for the synthesis of pyrazines

Liu, Kun; Song, Chunlan; Wu, Jiarong; Deng, Yuqi; Tang, Shan; Lei, Aiwen

doi:10.1039/c8gc03786h

Cited by 33 publications

(17 citation statements)

References 74 publications

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“…Using the iodide/iodine redox mediator, Lei et al. developed, using a graphite rod as anode and a platinum plate as a cathode in an undivided cell, a synthetic protocol for pyrazines ( 35 ) (Scheme 4); the indirect electrochemical oxidation of alkyl arylketones ( 33 ) allowed obtaining moderate to good yields of the dinitrogenated heterocycles (41–83 %) [40] . The electrochemically formed α‐iodo‐ketone ( 36 ) undergoes condensation and a consecutive nucleophilic substitution with 1,2‐diamines ( 34 ), in two steps promoted by an acid catalyst (TsOH).…”

Section: C‐centered Radicalsmentioning

confidence: 99%

Electrochemical Generation and Use in Organic Synthesis of C‐, O‐, and N‐Centered Radicals

Chicas-Baños

Frontana‐Uribe

2021

The Chemical Record

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During the last decade several research groups have been developing electrochemical procedures to access highly functionalized organic molecules. Among the most exciting advances, the possibility of using free radical chemistry has attracted the attention of the most important synthetic groups. Nowadays, electrochemical strategies based on these species with a synthetic purpose are published continuously in scientific journals, increasing the alternatives for the synthetic organic chemistry laboratories. Free radicals can be obtained in organic electrochemical reactions; thus, this review reassembles the last decade's (2010–2020) efforts of the electrosynthetic community to generate and take advantage of the C‐, O‐, and N‐centered radicals’ reactivity. The electrochemical reactions that occur, as well as the proposed mechanism, are discussed, trying to give clear information about the used conditions and reactivity of these reactive intermediate species.

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Section: C‐centered Radicalsmentioning

confidence: 99%

Electrochemical Generation and Use in Organic Synthesis of C‐, O‐, and N‐Centered Radicals

Chicas-Baños

Frontana‐Uribe

2021

The Chemical Record

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“…Previous reports for the synthesis of pyrazines often require the use of transition metal catalysts along with the stoichiometric amount of oxidants, which is not suitable for oxidatively labile groups with a reasonable amount of waste. Lei and co‐workers [42] employed an iodide mediator in combination with electro‐oxidative cyclization for the construction of pyrazine derivatives (Scheme 31). The reaction failed in the absence of an iodide mediator, presumably due to problems associated with over‐oxidation of ethylenediamine and reactive intermediates.…”

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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“…Lei's group reported on electrooxidative [4+2] annulation of aryl ketones 54 and diamines 55 which they applied to the synthesis of pyrazines 56 (Scheme ). The transformation proceeded in an undivided electrolytic condition with KI as the mediator of the process.…”

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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Electrochemical oxidation synergizing with Brønsted-acid catalysis leads to [4 + 2] annulation for the synthesis of pyrazines

Abstract: Electrochemical oxidative [4 + 2] annulation for the synthesis of pyrazines.

Cited by 33 publications

References 74 publications

Electrochemical Generation and Use in Organic Synthesis of C‐, O‐, and N‐Centered Radicals

Electrochemical Generation and Use in Organic Synthesis of C‐, O‐, and N‐Centered Radicals

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

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