An electrolysis cell with close consecutive flow-through porous electrodes for particular organic electrosynthesis

Lamoureux, Carl; Moinet, Claude; Tallec, A.

doi:10.1007/bf01006527

Cited by 18 publications

(13 citation statements)

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“…Moinet and co‐workers devised a strategy for generating nitroso compounds by first reducing nitroarenes (Scheme , 4a ) to hydroxylamines ( 4b ) that were in the next step re‐oxidized to nitroso compounds ( 4c ). For this purpose, they employed a flow cell in a galvanostatic mode using two consecutive porous graphite felt electrodes of opposite polarities . This ensures that the nitroso compound cannot form a redox‐pair with hydroxylamine that could lead to the formation of azoxy compounds and lower the yields.…”

Section: Nitro Derivativesmentioning

confidence: 99%

Recent Advances in the Electrochemical Reduction of Substrates Involving N−O Bonds

2020

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In this review,t he versatile and rich chemistry for the electrochemical reductiono fs ubstrates involving N À Ob onds is surveyed. By the cathodic treatment of nitro,n itroso and other oxygenated organic nitrogen substrates,v ersatile andr eactive intermediates are formed which can be subsequently converted to high value-added products. In many examples,n itrogen heterocycles are selectively formed, but, also depending on the electrolytic conditions, free oximes,n itrones,a mines and other entities can be obtained as well. Ther ecent decades have witnessed twom ajor advances-(i)g oing directly to more complext arget molecules and (ii)c onductingt he electrolysesi nm uch simpler set-ups.Both improvements make the cathodic access of the target compoundsm uch more practical and scalable. 1I ntroduction 2N itro Derivatives 2.1 IntermolecularReactions 2.2 IntramolecularReactions:Synthesis of Heterocycles 3O ximes 4O ther Functionalities 5C onclusions

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Section: Nitro Derivativesmentioning

confidence: 99%

Recent Advances in the Electrochemical Reduction of Substrates Involving N−O Bonds

2020

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“…The corresponding Nsulphonylhydroxylamine 2d was isolated in 44% yield and characterized. This product is identical with the one obtained by adding sodium p-toluenesulphinate to a solution of the nitroso compound electrogenerated from 2a [25] in a ''redox'' flow cell equipped with to consecutive porous electrodes of opposite polarities [26][27][28].…”

Section: Electrolysis and Coulometric Datamentioning

confidence: 99%

Electroreduction of (1S,2S)-2-amino-1-(4-nitrophenyl)-propane-1,3-diol derivatives. Behaviour of electrogenerated species and applications to organic synthesis

et al. 2005

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Hydroxylamines electrogenerated from (1S,2S)-2-amino-1-(4-nitrophenyl)-propane-1,3-diol derivatives (derivatives of p-nitrophenylserinol) are unstable in methanol-acetate buffer and practically stable in acetonitrile-aqueous acetate buffer. This latter medium was used to carry out subsequent reactions in situ involving the triacetylated p-hydroxylaminophenylserinol and various reagents. An azoxy compound was the major product isolated after reaction with maleic or phthalic anhydrides. In contrast, a benzoxazine dione was normally obtained with phthaloyl dichloride and a N-sulphonylated hydroxylamine was produced with p-toluenesulphonyl chloride.

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“…Thus, a range of sulfamide were provided in moderate to good yields (Scheme 27). [49] Li and co-workers illustrated the electrochemical intermolecular coupling reaction of isothiocyanates with 2-aminopyridines to access to 1,2,4-thiadiazloes (Scheme 28). [50] The n-Bu 4 NI served the both role of catalyst and electrolyte obviating use of external oxidants and transition-metal catalysts.…”

Section: Electrochemical Non-dehydrogenative Sà N Bond Formationmentioning

confidence: 99%

Electrochemical Heteroatom‐Heteroatom Bond Construction

Gao

et al. 2021

The Chemical Record

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Heteroatom-heteroatom linkage, with SÀ S bond as a presentative motif, served a crucial role in biochemicals, pharmaceuticals, pesticides, and material sciences. Thus, preparation of the privileged scaffold has always been attracting tremendous attention from the synthetic community. However, classic protocols suffered from several drawbacks, such as toxic and unstable agents, poor functional group tolerance, multiple steps, and explosive oxidizing regents as well as the transitional metal catalysts. Electrochemical organic synthesis exhibited a promising alternative to the traditional chemical reaction due to the sustainable electricity can be employed as the traceless redox agents. Hence, toxic and explosive oxidants and/or transitional metals could be discarded under mild reaction with high efficiency. In this context, a series of electrochemical approaches for the construction of heteroatom-heteroatom bond were reviewed. Notably, most of the cases illustrated the dehydrogenative feature with the clean energy molecules hydrogen as the sole by-product.

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An electrolysis cell with close consecutive flow-through porous electrodes for particular organic electrosynthesis

Cited by 18 publications

References 10 publications

Recent Advances in the Electrochemical Reduction of Substrates Involving N−O Bonds

Recent Advances in the Electrochemical Reduction of Substrates Involving N−O Bonds

Electroreduction of (1S,2S)-2-amino-1-(4-nitrophenyl)-propane-1,3-diol derivatives. Behaviour of electrogenerated species and applications to organic synthesis

Electrochemical Heteroatom‐Heteroatom Bond Construction

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