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

Yang, Qu; Tateno, Hiroyuki; Matsumura, Yoshihito; Kashiwagi, Tsuneo; Atobe, Mahito

doi:10.3390/molecules22030413

Cited by 8 publications

(5 citation statements)

References 22 publications

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“…Mechanism for the electroreductive coupling of aryl halides with arenes, shown for the reaction of 4-iodotoluenewith benzonitrile. [97] CÀCb ond. Rearomatization is achieved by base-assisted proton abstraction and electron transfer from the radical anion to the starting material.…”

Section: Reductive Couplings By Càha Ctivationmentioning

confidence: 99%

“…Such electroreductive coupling reactions were recently investigated by Atobe and co‐workers, who achieved the C−C cross‐coupling of an aryl halide with a second arene. The mechanistic rationale is shown in Scheme , and was described to involve a single electron transfer to the aryl halide and subsequent dehalogenation to give an aryl radical.…”

Section: Electrochemical Arene Couplingsmentioning

confidence: 99%

“… Mechanism for the electroreductive coupling of aryl halides with arenes, shown for the reaction of 4‐iodotoluene with benzonitrile …”

Section: Electrochemical Arene Couplingsmentioning

confidence: 99%

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Electrifying Organic Synthesis

et al. 2018

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The direct synthetic organic use of electricity is currently experiencing a renaissance. More synthetically oriented laboratories working in this area are exploiting both novel and more traditional concepts, paving the way to broader applications of this niche technology. As only electrons serve as reagents, the generation of reagent waste is efficiently avoided. Moreover, stoichiometric reagents can be regenerated and allow a transformation to be conducted in an electrocatalytic fashion. However, the application of electroorganic transformations is more than minimizing the waste footprint, it rather gives rise to inherently safe processes, reduces the number of steps of many syntheses, allows for milder reaction conditions, provides alternative means to access desired structural entities, and creates intellectual property (IP) space. When the electricity originates from renewable resources, this surplus might be directly employed as a terminal oxidizing or reducing agent, providing an ultra‐sustainable and therefore highly attractive technique. This Review surveys recent developments in electrochemical synthesis that will influence the future of this area.

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Section: Reductive Couplings By Càha Ctivationmentioning

confidence: 99%

Section: Electrochemical Arene Couplingsmentioning

confidence: 99%

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Electrifying Organic Synthesis

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“…A similar protocol was reported by Atobe and co-workers describing the cross-coupling reaction of aryl halides with arenes in a divided cell (see Scheme 59). 118 The authors describe a mechanistic rationale where a radical anion from the iodo arene is generated by a SET. In the next step an aryl radical is formed upon elimintion of I − .…”

Section: Cathodic Conversionmentioning

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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“…Such electroreductive coupling reactions were recently investigated by Atobe and co-workers, [97] who achieved the CÀCcross-coupling of an aryl halide with asecond arene.The mechanistic rationale is shown in Scheme 27, and was described to involve as ingle electron transfer to the aryl halide and subsequent dehalogenation to give an aryl radical. This radical is attacked by the coupling partner to form the Scheme 25.…”

Section: Reductive Couplings By Càha Ctivationmentioning

confidence: 99%

Elektrifizierung der organischen Synthese

et al. 2018

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Die direkte Nutzung von Elektrizität für die organische Synthese erlebt derzeit eine Renaissance. Von den eher syntheseorientierten Laboratorien, die auf diesem Gebiet arbeiten, werden neuartige oder althergebrachte Konzepte genutzt, um den Weg von der Nischentechnologie zu breiteren Anwendungen zu ebnen. Da nur Elektronen als Reagens genutzt werden, wird die Bildung von Abfallreagentien effizient vermieden. Darüber hinaus können stöchiometrische Reagentien regeneriert werden und ermöglichen eine elektrokatalysierte Umsetzung. Die Anwendung von elektroorganischen Transformationen ist jedoch mehr als nur die Minimierung des Abfallaufkommens; sie führt vielmehr zu inhärent sicheren Prozessen, zur Abkürzung vieler Synthesestufen, zu milderen Reaktionsbedingungen, zu alternativen Zugängen zu gewünschten Struktureinheiten sowie zur Schaffung neuer Bereiche für geistiges Eigentum (Patente). Wenn die verwendete Elektrizität aus regenerativen Ressourcen stammt, kann dieser Stromüberschuss direkt als terminales Oxidations‐ oder Reduktionsmittel eingesetzt werden, was eine äußerst nachhaltige und damit hochattraktive Technologie darstellt. Dieser Aufsatz gibt einen Überblick über die jüngsten Entwicklungen auf dem Gebiet der elektrochemischen Synthese, welche die Zukunft dieses stark aufstrebenden Gebietes beeinflussen werden.

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

Cited by 8 publications

References 22 publications

Electrifying Organic Synthesis

Electrifying Organic Synthesis

Electrochemical Arylation Reaction

Elektrifizierung der organischen Synthese

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