Electrolytic Partial Fluorination of Organic Compounds. 14. The First Electrosynthesis of Hypervalent Iodobenzene Difluoride Derivatives and Its Application to Indirect Anodic gem-Difluorination

Fuchigami, Toshio; Fujita, Toshio

doi:10.1021/jo00103a003

Cited by 167 publications

(94 citation statements)

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“…Previously, Yoneda et al and we found that anodic fluorination of p-methyl-, p-nitro-, p-methoxyiodobenzenes afforded the corresponding iodobenzene difluoride derivatives in moderate to good yields, as shown in Scheme 3 [11,12].…”

Section: Anodic Fluorination Of Benzylphosphonate Derivativesmentioning

confidence: 61%

Electrolytic partial fluorination of organic compounds 84

Zagipa¹,

Hidaka²,

Cao³

2006

Journal of Fluorine Chemistry

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Section: Anodic Fluorination Of Benzylphosphonate Derivativesmentioning

confidence: 61%

Electrolytic partial fluorination of organic compounds 84

Zagipa¹,

Hidaka²,

Cao³

2006

Journal of Fluorine Chemistry

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“…Interestingly,a nisole-derived iodoarenes performed best (Scheme 3). [25,26] Task-specific iodoarenes,carrying,for example,animidazolium moiety, [27] and polymer-supported iodoarenes [28] have also been developed. These are stable during the electrochemical reaction and product extraction, and can be reused in subsequent runs.T hese developments culminated in ahighly selective method for the electrochemical fluorination of (hetero)aromatic compounds under mild reaction conditions.…”

Section: Electrochemical Fluorinationmentioning

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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“…27) The fluorination reactions that use catalytic amounts of trivalent reagents were reported under electrolytic conditions in 1994, 28) but this did not become a general method because the oxidation potential of iodobenzene is comparatively high and thus many organic compounds potentially cause undesired noncatalyst-participating background reactions under electrolytic conditions required for regeneration of the catalyst. Therefore the reaction, which makes the reagents catalytic, was not reported in the literature until 2005.…”

Section: Application Of the Regeneration Process Of The Recyclable Rementioning

confidence: 99%

Recycling and Catalytic Approaches for the Development of a Rare-Metal-Free Synthetic Method Using Hypervalent Iodine Reagent

Dohi

2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Oxidation reactions consist of a number of important transformations in organic synthesis. However, in spite of their utility in both laboratory-and industrial-scale production, oxidations are among the most problematic processes regarding the factors of safety, environmental friendliness, operational simplicity, etc. As oxidants, hypervalent iodines, such as phenyliodine(III) diacetate (PIDA) and phenyliodine(III) bis(trifluoroacetate) (PIFA), are among promising reagents for developing environmentally benign oxidation reactions due to their low toxicities, mild reactivity, ready availability, high stability, and easy handling. Our research objective is, largely in consideration of economic and environmental viewpoints, to enhance the synthetic values of these reagents as useful alternatives to highly toxic heavy-metal oxidants and even rare transition metals by pioneering their efficient utilization methods and unique reactivities. During this study, we have succeeded in the development of new recyclable reagents 1 and their catalytic utilization, and the design of a new chiral reagent 2 and its application to perform asymmetric oxidations. Accordingly, the recycling and catalytic use of a hypervalent iodine reagent became possible in many representative types of oxidative bond-forming reactions, some of which even include key transformations for natural product synthesis. A summary of these important achievements in hypervalent iodine chemistry are described in this review.

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Electrolytic Partial Fluorination of Organic Compounds. 14. The First Electrosynthesis of Hypervalent Iodobenzene Difluoride Derivatives and Its Application to Indirect Anodic gem-Difluorination

Cited by 167 publications

References 0 publications

Electrolytic partial fluorination of organic compounds 84

Electrolytic partial fluorination of organic compounds 84

Elektrifizierung der organischen Synthese

Recycling and Catalytic Approaches for the Development of a Rare-Metal-Free Synthetic Method Using Hypervalent Iodine Reagent

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