Electrochemical Performance of ABNO for Oxidation of Secondary Alcohols in Acetonitrile Solution

Niu, Pengfei; Liu, Xin; Shen, Zhenlu; Li, Meichao

doi:10.3390/molecules24010100

Cited by 13 publications

(11 citation statements)

References 72 publications

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“…At the cathode, the proton released from the alcohol oxidation step is reduced to H 2 (hydrogen evolution reaction). 18,26–28,40 This is supported by the observation of bubbles formed on the cathode surface over the course of the reaction.…”

Section: Resultsmentioning

confidence: 78%

Acetamido-TEMPO mediated electrochemical oxidation of alcohols to aldehydes and ketones

Schroeder,

Politano,

Ohlhorst

et al. 2023

RSC Adv.

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Section: Resultsmentioning

confidence: 78%

Acetamido-TEMPO mediated electrochemical oxidation of alcohols to aldehydes and ketones

Schroeder,

Politano,

Ohlhorst

et al. 2023

RSC Adv.

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“…However, mainly due to the complex and weak NMR signals, we could not obtain useful information except for the presence of small aromatic compounds bearing G-aromatic nuclei. 2,6-Lutidine has been reported to promote electrooxidations as a base in EMS using various mediators such as N-hydroxyphthalimide, 13,18,37 9-azabicyclo[3.3.1]nonane-Noxyl, 38 TEMPO, 39 and AcNH-TEMPO. 15 Accordingly, we tested the effect of 2,6-lutidine (2 equiv relative to the mediator) on the Fe(bpy) 3 -mediated electro-oxidation of G-DHP in 0.1 M LiClO 4 /70%-CH 3 CN/H 2 O.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…2,6-Lutidine has been reported to promote electro-oxidations as a base in EMS using various mediators such as N -hydroxyphthalimide, ,, 9-azabicyclo[3.3.1]nonane- N -oxyl, TEMPO, and AcNH-TEMPO . Accordingly, we tested the effect of 2,6-lutidine (2 equiv relative to the mediator) on the Fe(bpy) 3 -mediated electro-oxidation of G-DHP in 0.1 M LiClO 4 /70%-CH 3 CN/H 2 O.…”

Section: Results and Discussionmentioning

confidence: 99%

Electro-Oxidation of Lignin Model Compounds and Synthetic Lignin with Transition-Metal Complexes (Manganese and Iron Complexes)

Xie

Tobimatsu

Narita

et al. 2022

ACS Sustainable Chem. Eng.

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Transition-metal complexes Mn(acac) 2 , Mn(bpy) 3 , Fe(acac) 2 , and Fe(bpy) 3 were investigated as mediators in lignin oxidation with an electrolytic mediator system (EMS). Fe(bpy) 3 was screened among them as a mediator in the bulk electrolysis of a lignin dimer model compound (4-ethoxy-3-methoxyphenylglycerol-β-guaiacyl ether: 3G) and guaiacyl-type dehydrogenation polymer (G-DHP) by experiments using the lignin monomer model compound 1-(4-ethoxy-3-methoxyphenyl)ethanol. In Fe(bpy) 3 -mediated electro-oxidations of compound 3G, both Cα−Cβ cleavage and Cα-carbonylation proceeded efficiently in 0.1 M LiClO 4 /70%-CH 3 CN/H 2 O, whereas Cαcarbonylation predominated in 10%-dioxane/0.1 M acetate buffer (pH 4). Fe(bpy) 3 -mediated electro-oxidation of G-DHP also proceeded efficiently via both Cα−Cβ cleavage and Cα-carbonylation in 0.1 M LiClO 4 /70%-CH 3 CN/ H 2 O. The oxidation was promoted by the addition of 2,6-lutidine as a base. By contrast, the Fe(bpy) 3 -mediated electro-oxidations of G-DHP did not proceed efficiently in 10%-dioxane/0.1 M acetate buffer (pH 4) with or without 2,6-lutidine under the present conditions. It was reconfirmed that electrolyte was also one of the important factors in lignin oxidation with EMS. Consequently, Fe(bpy) 3 was found to be a promising mediator of lignin EMS for lignin modification and degradation.

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“…1350 cm –1 for nitroxide radicals and ca. 1600 cm –1 for oxoammonium cations , ). The position of ν(N–O) at 1015–963 cm –1 in [M(tacn)(tfo)] + complexes is indicative of a single nitrogen–oxygen bond, while the mixed valency of the ligand would result in a much higher frequency (intermediate between hydroxylamine and nitroxide radical or oxoammonium cation).…”

Section: Resultsmentioning

confidence: 99%

Revealing the Structure of Transition Metal Complexes of Formaldoxime

et al. 2021

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Aerobic reactions of iron(III), nickel(II), and manganese(II) chlorides with formaldoxime cyclotrimer (tfoH 3 ) and 1,4,7-triazacyclononane (tacn) produce indefinitely stable complexes of general formula [M(tacn)(tfo)]Cl. Although the formation of formaldoxime complexes has been known since the end of 19th century and applied in spectrophotometric determination of Dmetals (formaldoxime method), the structure of these coordination compounds remained elusive until now. According to the X-ray analysis, [M(tacn)(tfo)] + cation has a distorted adamantane-like structure with the metal ion being coordinated by three oxygen atoms of deprotonated tfoH 3 ligand. The metal has a formal +4 oxidation state, which is atypical for organic complexes of iron and nickel. Electronic structure of [M(tacn)(tfo)] + cations was studied by XPS, NMR, cyclic (CV) and differential pulse (DPV) voltammetries, Mossbauer spectroscopy, and DFT calculations. Unusual stabilization of high-valent metal ion by tfo 3− ligand was explained by the donation of electron density from the nitrogen atom to the antibonding orbital of the metal−oxygen bond via hyperconjugation as confirmed by the NBO analysis. All complexes [M(tacn)(tfo)]Cl exhibited high catalytic activity in the aerobic dehydrogenative dimerization of p-thiocresol under ambient conditions.

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Electrochemical Performance of ABNO for Oxidation of Secondary Alcohols in Acetonitrile Solution

Cited by 13 publications

References 72 publications

Acetamido-TEMPO mediated electrochemical oxidation of alcohols to aldehydes and ketones

Acetamido-TEMPO mediated electrochemical oxidation of alcohols to aldehydes and ketones

Electro-Oxidation of Lignin Model Compounds and Synthetic Lignin with Transition-Metal Complexes (Manganese and Iron Complexes)

Revealing the Structure of Transition Metal Complexes of Formaldoxime

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