Electrochemical oxidation of catechols in the presence of ethyl‐2‐chloroacetoacetate. Synthesis and mechanistic study

Shamsipur, Mojtaba; Davarani, Saied Saeed Hosseiny; Nematollahi, Davood

doi:10.1002/jhet.5570430638

Cited by 7 publications

(3 citation statements)

References 19 publications

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“…In the course of the electrolysis, the enolate subunit of 4-hydrocoumarin undergoes subsequent inter- and intramolecular Michael addition reactions with in situ electrogenerated o -benzoquinone moiety, first leading to the C–C bond and then to the C–O bond formation, to finally afford the benzoxazole heterocycle. In this way, Tabaković and other scientists from Iran have employed a variety of enolates, such as 350 – 355 as the C,O-doubly nucleophiles to construct various benzoxazole derivatives. − …”

Section: Intermolecular Cyclizationmentioning

confidence: 99%

Use of Electrochemistry in the Synthesis of Heterocyclic Structures

2017

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The preparation and transformation of heterocyclic structures have always been of great interest in organic chemistry. Electrochemical technique provides a versatile and powerful approach to the assembly of various heterocyclic structures. In this review, we examine the advance in relation to the electrochemical construction of heterocyclic compounds published since 2000 via intra- and intermolecular cyclization reactions.

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Section: Intermolecular Cyclizationmentioning

confidence: 99%

Use of Electrochemistry in the Synthesis of Heterocyclic Structures

2017

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“…A variety of transformations for delivering annulated scaffolds have also been developed (Scheme 89). In the pursuit of this goal, a range of different benzofurans (291 and 293) have been accessed using 1,3-diketones, [745][746][747][748][749][750][751][752][753][754][755][756] a-cyanoketones 757 774 derivatives. Furthermore, the electrochemically generated benzoquinone derivatives can also engage in [4+2] cycloaddition in the presence of cyclopentadiene, 775,776 produce trimerization products [777][778][779] or engage in transfer hydrogenation catalysis.…”

Section: Electrochemical Oxidative Cross-couplingsmentioning

confidence: 99%

Electrochemical strategies for C–H functionalization and C–N bond formation

2018

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Conventional methods for carrying out carbon-hydrogen functionalization and carbon-nitrogen bond formation are typically conducted at elevated temperatures, and rely on expensive catalysts as well as the use of stoichiometric, and perhaps toxic, oxidants. In this regard, electrochemical synthesis has recently been recognized as a sustainable and scalable strategy for the construction of challenging carbon-carbon and carbon-heteroatom bonds. Here, electrosynthesis has proven to be an environmentally benign, highly effective and versatile platform for achieving a wide range of nonclassical bond disconnections via generation of radical intermediates under mild reaction conditions. This review provides an overview on the use of anodic electrochemical methods for expediting the development of carbon-hydrogen functionalization and carbon-nitrogen bond formation strategies. Emphasis is placed on methodology development and mechanistic insight and aims to provide inspiration for future synthetic applications in the field of electrosynthesis.

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“…By adding a chloro substituent at position 2 of the diketone, the former four-electron oxidation sequence is converted into a two-electron oxidation (Scheme ). − Even a 2-fold Michael-type addition is viable, whereby a pentacyclic system is formed (Scheme ). …”

Section: Arylation Of Specific Groupsmentioning

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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Electrochemical oxidation of catechols in the presence of ethyl‐2‐chloroacetoacetate. Synthesis and mechanistic study

Cited by 7 publications

References 19 publications

Use of Electrochemistry in the Synthesis of Heterocyclic Structures

Use of Electrochemistry in the Synthesis of Heterocyclic Structures

Electrochemical strategies for C–H functionalization and C–N bond formation

Electrochemical Arylation Reaction

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