Anodic Oxidation of 4-Allyl-2-Methoxyphenol Syntheses of Demethoxyasatone and Demethoxyisoasatone

Iguchi, Masanobu; Nishiyama, Atsuko; Terada, Yukimasa; Yamamura, Shosuke

doi:10.1246/cl.1978.451

Cited by 26 publications

(12 citation statements)

References 5 publications

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“…The electrooxidation of vanillin and eugenol on platinum in basic media into the corresponding natural occurring biphenols has been reported. [13,14] Owing to the high costs of platinum, carbon electrode materials are definitely more attractive for technical applications. Unfortunately, the conversion of simple methylated phenols like para-cresol or 2,4-dimethylphenol (1) lead to the formation of the corresponding Pummerers ketone derivative 3 and not to the biphenol.…”

Section: Introductionmentioning

confidence: 99%

Highly Selective Electrosynthesis of Biphenols on Graphite Electrodes in Fluorinated Media

Kirste

Hayashi

Schnakenburg

et al. 2011

Chemistry A European J

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The direct and selective phenol coupling reaction that provides biphenols still represents a challenge in organic synthesis. The recently developed electrosynthesis on boron-doped diamond anodes with fluorinated additives was developed further to allow the application to less-expensive electrodes and fluorinated media. This advanced protocol allows the highly selective anodic phenol coupling reaction on graphite with a broad scope.

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Section: Introductionmentioning

confidence: 99%

Highly Selective Electrosynthesis of Biphenols on Graphite Electrodes in Fluorinated Media

Kirste

Hayashi

Schnakenburg

et al. 2011

Chemistry A European J

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“…637 Some of these dihydrobenzofuran derivatives display fluorescent properties, 638,639 a feature which has been exploited for fluorescent labeling of amino acid derivatives 640 as well as homonucleosides. 641 In addition, the electrochemically produced cyclohexadienone derivatives have also been reported to engage in [4+2] [642][643][644][645][646][647][648] and [5+2] [649][650][651][652] cycloadditions. 653 Alternatively, incorporation of a pending nucleophile into the phenol unit allows the design of various types of intramolecular reaction manifolds for construction of spirodienone derivatives.…”

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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“…Neutral conditions appear to favor the formation of cationic intermediates such as 6 through two-electron oxidation ( Figure 3). These phenoxenium ions can be rapidly quenched in MeOH to furnish ortho-quinone monoketals such as 1c ( Figure 3, R ¼ Nu ¼ OMe), but electrolysis of the same starting phenols in a basic medium at a lower oxidation potential predominantly gives dimers resulting from phenoxy radical coupling [35,36,[62][63][64]. Such divergent behavior of arenols has been clearly delineated by Yamamura and co-workers, who showed, inter alia, that eugenol (29) is converted to the ortho-quinone monoketal 30 in 68 % yield when electrolyzed in MeOH at a constant current (90 mA, 0.56 mA cm À2 , þ750-780 mV vs. SCE) using a platinum anode and LiClO 4 as the supporting electrolyte ( Figure 10) [36].…”

Section: Anodic Oxidationmentioning

confidence: 99%

Oxidative Conversion of Arenols into ortho ‐Quinols and ortho ‐Quinone Monoketals – A Useful Tactic in Organic Synthesis

Quideau

2002

Modern Arene Chemistry

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The oxidative activation of arenes is a powerful and versatile synthetic tactic that enables dearomatization to give useful synthons. Central to this chemistry are hydroxylated arenes or arenols, the phenolic functions of which can be exploited to facilitate the dearomatizing process by two-electron oxidation. Suitably substituted arenols can hence be converted, with the help of oxygen-or carbon-based nucleophiles, into ortho-quinone monoketals and ortho-quinols. These 6-oxocyclohexa-2,4-dienones are ideally functionalized for the construction of many complex and polyoxygenated natural product architectures. Today, the inherent and multiple reactivity of arenol-derived ortho-quinone monoketals and orthoquinols species is finding numerous and, in many cases, biomimetic applications in modern organic synthesis. 15.1

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Anodic Oxidation of 4-Allyl-2-Methoxyphenol Syntheses of Demethoxyasatone and Demethoxyisoasatone

Cited by 26 publications

References 5 publications

Highly Selective Electrosynthesis of Biphenols on Graphite Electrodes in Fluorinated Media

Highly Selective Electrosynthesis of Biphenols on Graphite Electrodes in Fluorinated Media

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

Oxidative Conversion of Arenols into ortho ‐Quinols and ortho ‐Quinone Monoketals – A Useful Tactic in Organic Synthesis

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