Homogeneous electro-mediated reduction of unsaturated compounds using Ni and Fe as mediators in DMF

Silva, Aderivaldo P. da; Mota, Saulo D.C.; Bieber, Lothar W.; Navarro, Marcelo

doi:10.1016/j.tet.2006.03.067

Cited by 30 publications

(18 citation statements)

References 20 publications

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“…The chemical reduction of piperine under various conditions has been reported (da Silva, Mota, Bieber & Navarro, 2006;Gallagher, Shimmon & McDonagh, 2012;Pedersen et al, 2009). Either of the two carbon-carbon double bonds has been generally suggested to undergo hydrogenation in methanol (or ethanol) with a catalyst or mediator (Gallagher et al, 2012), although reduction leading to a , unsaturated amide was also claimed (da Silva et al, 2006;Pedersen et al, 2009). For the electrochemical reduction as discussed above, a possible mechanism explaining the difference between the micro-and macro-electrode voltammetry is shown in Figure 1(E), Section 3.1.1.…”

Section: Possible Reaction Mechanismmentioning

confidence: 99%

Electrochemical quantification of piperine in black pepper

et al. 2020

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A simple, rapid method of the detection of piperine in black pepper is reported using a voltammetric sensor based on a glassy carbon electrode (GC) with analysis following a short one-step extraction using ethanol. The method is based on a novel potential sweep designed to maximise signal sizes and shown with context of the present analytical challenge to be essential for gathering data allowing the construction of a linear calibration curve for the analysis in the relevant range namely 0.25-5.0 mM.

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Section: Possible Reaction Mechanismmentioning

confidence: 99%

Electrochemical quantification of piperine in black pepper

et al. 2020

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“…In the present work, we decided on a more challenging task of electrochemically induced intermolecular cross-dehydrogenative C–O coupling of β-dicarbonyl compounds with carboxylic acids with high yields at CCE in an undivided cell (Scheme , c). Despite the fact that many processes of anodic nature, ,− such as hydroxylation, − halogenation, dimerization, and cathodic nature, for example, carbonyl group reduction, − can take place in similar systems (Scheme , a), an acyloxy-product is selectively formed under our conditions.…”

Section: Introductionmentioning

confidence: 92%

Electrochemically Induced Intermolecular Cross-Dehydrogenative C–O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids

et al. 2019

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The electrochemically induced cross-dehydrogenative C–O coupling of β-diketones and β-ketoesters (C–H reagents) with carboxylic acids (O–H reagents) was developed. An important feature of this reaction lies in the selective formation of intermolecular C–O coupling products in high yields, up to 92%, using DMSO as a solvent with a broad substrate scope in an undivided cell equipped with carbon and platinum electrodes at high current density. Electric current acts as a stoichiometric oxidant.

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“…Another important challenge is here to reduce the carbonyl to the alcohol in a chemoselective way, avoiding the ketyl radical coupling and the hydrogenation of other unsaturations (e.g., C=C) when present ( Figure 5 b). 48 , 49 To drive carbonyl hydrogenation to the desired selectivity, molecular electrocatalysts have been investigated, 50 , 51 mostly based on Ni, 52 , 53 Fe, 52 , 53 Ru, 54 and Rh 55 − 57 metal complexes, with a body of work using homogeneous and immobilized Rh bipyridine type complexes. 55 − 57 …”

Section: Case Studiesmentioning

confidence: 99%

Electrocatalysis with Molecular Transition-Metal Complexes for Reductive Organic Synthesis

Kaeffer

Leitner

2022

JACS Au

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Electrocatalysis enables the formation or cleavage of chemical bonds by a genuine use of electrons or holes from an electrical energy input. As such, electrocatalysis offers resource-economical alternative pathways that bypass sacrificial, waste-generating reagents often required in classical thermal redox reactions. In this Perspective, we showcase the exploitation of molecular electrocatalysts for electrosynthesis, in particular for reductive conversion of organic substrates. Selected case studies illustrate that efficient molecular electrocatalysts not only are appropriate redox shuttles but also embrace the features of organometallic catalysis to facilitate and control chemical steps. From these examples, guidelines are proposed for the design of molecular electrocatalysts suited to the reduction of organic substrates. We finally expose opportunities brought by catalyzed electrosynthesis to functionalize organic backbones, namely using sustainable building blocks.

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Homogeneous electro-mediated reduction of unsaturated compounds using Ni and Fe as mediators in DMF

Cited by 30 publications

References 20 publications

Electrochemical quantification of piperine in black pepper

Electrochemical quantification of piperine in black pepper

Electrochemically Induced Intermolecular Cross-Dehydrogenative C–O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids

Electrocatalysis with Molecular Transition-Metal Complexes for Reductive Organic Synthesis

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