Ueber die Bildung von Alkoholen bei der Elektrolyse fettsaurer Salze

Hofer, Hans Werner; Moest, M.

doi:10.1002/jlac.19023230304

Cited by 113 publications

(71 citation statements)

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“…Finally, an excellent current efficiency ranging from 75 % to 80 % was observed when considering a theoretical consumption of 2 F/mol of substrate, a flow of 0.15 mL/min and a pathway of 2 mL within the cell. Such high current efficiency is unusual for Kolbe/Hoefer‐Moest reactions and might be explained by the facts that a potassium carboxylate was used and by the very small gap between the two electrodes …”

Section: Figurementioning

confidence: 99%

Supporting‐Electrolyte‐Free Electrochemical Methoxymethylation of Alcohols Using a 3D‐Printed Electrosynthesis Continuous Flow Cell System

et al. 2019

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We describe the development of a novel low‐cost small‐footprint 3D‐printed electrosynthesis continuous flow cell system that was designed and adapted to fit a commercially available Electrasyn 2.0. The utility and effectiveness of the combined flow/electrochemistry system over the batch process was demonstrated in the development of an improved and supporting‐electrolyte‐free version of our anodic methoxymethylation of alcohols.

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Section: Figurementioning

confidence: 99%

Supporting‐Electrolyte‐Free Electrochemical Methoxymethylation of Alcohols Using a 3D‐Printed Electrosynthesis Continuous Flow Cell System

et al. 2019

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“…d) A phosphono-tetrapeptide prepared by Michaelis-Arbuzov reaction from the corresponding methoxy derivative by treatment with P(OC 6 H 5 ) 3 /TiCl 4 in CH 2 Cl 2 . 5 Our originally used term self-reproduction has, unfortunately, survived in numerous publications and patents. Urged by my colleague and mentor V. Prelog, who argued that self-reproduction should be strictly reserved for living systems, we had switched to selfregeneration.…”

Section: Scheme 2 Products Of Kolbe Couplings With (R)-444-trifluomentioning

confidence: 99%

Preparation of Enantiomerically Pure Compounds Employing Anodic Oxidations of Carboxylic Acids – A Late Review of Research Done in the 1980ies

Seebàch

2019

Helvetica Chimica Acta

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There are widely unknown enantiopure building blocks and non‐conventional transformations described in this old work that could become useful in today's diversity‐oriented organic synthesis world. Coupling and mixed couplings of functionalized CF3‐substituted chiral radicals by Kolbe electrolysis of carboxylic acids lead to hexafluoro‐hexane‐2,5‐diol and to butyro‐ and valerolactone derivatives with functional‐group relationships that normally require components with reactivity umpolung. Oxidative decarboxylation of amino‐acid and peptide derivatives by Hofer‐Moest electrolyses provide entry into the synthetic use of chiral acyliminium‐ion intermediates. Chiral oxazoline and thioazoline building blocks (from serine, threonine, and cysteine) are accessible for substitutions and cycloadditions. The stereochemical course of oxidative CO2H replacement in serine by nucleophilically introduced groups with retention of configuration is discussed.

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“…[61] If the electron transfer to the carboxylic acid occurs from atethered moiety with alower oxidation potential, such as electron-rich arenes, the reaction is termed pseudo-Kolbe reaction. [62] Theo utcome of aK olbe electrolysis depends mainly on the reaction conditions.C urrent density,s ubstrate concentration, and pH value are major factors.…”

Section: Scheme 14mentioning

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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Ueber die Bildung von Alkoholen bei der Elektrolyse fettsaurer Salze

Cited by 113 publications

References 1 publication

Supporting‐Electrolyte‐Free Electrochemical Methoxymethylation of Alcohols Using a 3D‐Printed Electrosynthesis Continuous Flow Cell System

Supporting‐Electrolyte‐Free Electrochemical Methoxymethylation of Alcohols Using a 3D‐Printed Electrosynthesis Continuous Flow Cell System

Preparation of Enantiomerically Pure Compounds Employing Anodic Oxidations of Carboxylic Acids – A Late Review of Research Done in the 1980ies

Elektrifizierung der organischen Synthese

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