Electrolysis in Non-nucleophilic Media. Part III. Anodic Coupling of Some 5-Alkyl-substituted m-Xylenes.

Nyberg, Klas; Kimmel, Ella C.; Holm, Beryl; Widmark, Gunnar; Koskikallio, Jouko; Kachi, Sukeji

doi:10.3891/acta.chem.scand.25-2983

Cited by 14 publications

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“…Therefore, modern C,H activating electrochemical coupling reactions are high standard to develop green synthetic processes. , One strategy to accomplish that is the 2-fold C,H activation for biaryl formation by anodic treatment of starting materials. The research of such transformations started in the late 20th century. − …”

Section: Aryl–aryl Bond Formationmentioning

confidence: 99%

Electrochemical Arylation Reaction

et al. 2018

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Arylated products are found in various fields of chemistry and represent essential entities for many applications. Therefore, the formation of this structural feature represents a central issue of contemporary organic synthesis. By the action of electricity the necessity of leaving groups, metal catalysts, stoichiometric oxidizers, or reducing agents can be omitted in part or even completely. The replacement of conventional reagents by sustainable electricity not only will be environmentally benign but also allows significant short cuts in electrochemical synthesis. In addition, this methodology can be considered as inherently safe. The current survey is organized in cathodic and anodic conversions as well as by the number of leaving groups being involved. In some electroconversions the reagents used are regenerated at the electrode, whereas in other electrotransformations free radical sequences are exploited to afford a highly sustainable process. The electrochemical formation of the aryl-substrate bond is discussed for aromatic substrates, heterocycles, other multiple bond systems, and even at saturated carbon substrates. This survey covers most of the seminal work and the advances of the past two decades in this area.

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Section: Aryl–aryl Bond Formationmentioning

confidence: 99%

Electrochemical Arylation Reaction

et al. 2018

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“…The electrochemical approach for the aromatic C,C cross-coupling is economically and environmentally attractive because only electrons serve as reagents and the reaction proceeds under a mild condition [ 11 , 12 ]. Although a number of aromatic C,C cross-coupling reactions by electrochemical method have been developed so far, most of these studies were based on the anodic oxidation process [ 13 , 14 , 15 , 16 , 17 , 18 , 19 ]. Anodic oxidation in the mixture of two aromatic compounds can provide cross-coupling products, but their selectivities are usually low [ 16 , 17 , 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

Cathodic Aromatic C,C Cross-Coupling Reaction via Single Electron Transfer Pathway

et al. 2017

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We have successfully developed a novel cathodic cross-coupling reaction of aryl halides with arenes. Utilization of the cathodic single electron transfer (SET) mechanism for activation of aryl halides enables the cross-coupling reaction to proceed without the need for any transition metal catalysts or single electron donors in a mild condition. The SET from a cathode to an aryl halide initiates a radical chain by giving an anion radical of the aryl halide. The following propagation cycle also consists entirely of anion radical intermediates.

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Electrochemically Initiated Radical Reactions

Bohn

Paul

Hilt

2012

Encyclopedia of Radicals in Chemistry, Biology and Materials

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This article reports on the applications of electrochemistry for the generation of radicals as neutral, cationic, and anionic intermediates and their use in preparative reactions for the formation of carbon–carbon and carbon–heteroatom bonds. The focus of this article is on electrochemical oxidation reactions of enol ethers, ketene acetals, and electron‐rich aromatic compounds. Furthermore, recent advances in the electrochemically induced synthesis of four‐membered ring systems and biaryl compounds are covered. The oxidative carbon–carbon bond formation by Kolbe electrolysis concludes the section dealing with oxidative transformations. The section describing reductive processes consists of indirect electrochemical reduction of alkylhalides and thioesters, as well as the reductive interconversion of functional groups described recently.

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Electrolysis in Non-nucleophilic Media. Part III. Anodic Coupling of Some 5-Alkyl-substituted m-Xylenes.

Cited by 14 publications

References 0 publications

Electrochemical Arylation Reaction

Electrochemical Arylation Reaction

Cathodic Aromatic C,C Cross-Coupling Reaction via Single Electron Transfer Pathway

Electrochemically Initiated Radical Reactions

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