An Environmentally Friendly Electrochemical Method for Synthesis of Benzofuranoquinone Derivatives

Davarani, Saied Saeed Hosseiny; Shamsipur, Mojtaba; Nematollahi, Davood; Ramyar, Somayyeh; Masoumi, Leila

doi:10.1248/cpb.55.1198

Cited by 6 publications

(2 citation statements)

References 22 publications

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“…24,25 In this cyclic voltammogram, the anodic and cathodic peaks ͑A 2 and C 2 ͒ correspond to the oxidation and reduction of 4a. 26 Furthermore, it is seen that, proportional to the augmentation of potential sweep rate, the height of the C 1 peaks increases ͑Fig. 2, curves a-e͒.…”

Section: Resultsmentioning

confidence: 92%

Electro-Organic Synthesis of Thioether and Benzofuran Derivatives

Davarani¹,

Ramyar²,

Masoumi³

et al. 2008

J. Electrochem. Soc.

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The electro-oxidation of 2,3-dimethylhydroquinone ͑1͒ has been studied in the presence of 2-hydroxy-1,4-naphthoquinone ͑4a͒, 2-mercaptobenzothiazole ͑3b͒, 2-mercaptobenzoxazole ͑3c͒, and thiazoline-2-thiol ͑3d͒ in aqueous solution, using cyclic voltammetry and controlled-potential coulometry. The results indicate that p-benzoquinone, generated by the electrochemical oxidation of 2,3-dimethylhydroquinone, is scavenged by 4a and 3b-3d to give the related products 7a, 5b-5d via various electrochemical mechanisms.

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Section: Resultsmentioning

confidence: 92%

Electro-Organic Synthesis of Thioether and Benzofuran Derivatives

Davarani¹,

Ramyar²,

Masoumi³

et al. 2008

J. Electrochem. Soc.

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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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