Using silver cathodes for organic electrosynthesis and mechanistic studies

Mubarak, Mohammad S.; Peters, Dennis G.

doi:10.1016/j.coelec.2017.03.001

Cited by 16 publications

(3 citation statements)

References 35 publications

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“…The voltammetric curves of 1a show the presence of different reduction peaks which are affected by the solvent and by the electrode material (see peak potential Table S1 in Supporting Information File 1 ). These voltammograms (and the data reported in Supporting Information File 1 , Table S1) evidence the catalytic effect of the silver cathode in the C–Br bond reduction ( E p1 is quite less negative on Ag cathode) [ 28 – 29 ], although this effect is more evident in DMF than in ACN. In any voltammogram, the cathodic peak at the less negative potential should be related to the cleavage of the C–Br bond.…”

Section: Resultsmentioning

confidence: 66%

Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene

Pandolfi¹,

Chiarotto²,

Feroci³

2018

Beilstein J. Org. Chem.

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The electrochemical reduction of 2-(2,2-dibromovinyl)naphthalene in a DMF solution (Pt cathode) yields selectively 2-ethynylnaphthalene or 2-(bromoethynyl)naphthalene in high yields, depending on the electrolysis conditions. In particular, by simply changing the working potential and the supporting electrolyte, the reaction can be directed towards the synthesis of the terminal alkyne (Et4NBF4) or the bromoalkyne (NaClO4). This study allowed to establish that 2-(bromoethynyl)naphthalene can be converted into 2-ethynylnaphthalene by cathodic reduction.

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Section: Resultsmentioning

confidence: 66%

Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene

Pandolfi¹,

Chiarotto²,

Feroci³

2018

Beilstein J. Org. Chem.

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“…For example, electrochemical reduction of pesticide residues containing carbon-halogen bonds allows their removal from environment, so as to improve human health and food safety. [1,2] On another and more fundamental electrochemical grounds, the reductive cleavage of carbon-halogen bonds has rapidly established itself as the model system of concerted or non-concerted bond breaking electron transfer. [3][4][5] There are indeed two main possible pathways to reductively cleave carbon-halogen bonds.…”

Section: Introductionmentioning

confidence: 99%

A DFT and SERS study of synergistic roles of thermodynamics and kinetics during the electrocatalytic reduction of benzyl chloride at silver cathodes

Chen

Weng

Cai

et al. 2022

Journal of Electroanalytical Chemistry

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“…Carbon and silver cathode materials were chosen, as carbon is inexpensive and convenient, and silver presents an attractive choice of cathode material due to its catalytic activity in the cleavage of carbon-halogen bonds. [23][24][25]…”

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confidence: 99%

Direct Electrochemical Reduction of Acetochlor at Carbon and Silver Cathodes in Dimethylformamide

Petro

Thapa

Karty

et al. 2020

J. Electrochem. Soc.

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Cyclic voltammetry and controlled-potential (bulk) electrolysis have been employed to investigate the direct electrochemical reduction of acetochlor (1) at carbon and silver cathodes in dimethylformamide. Voltammograms of 1 exhibit a single irreversible cathodic peak at both cathode materials. Catalytic properties of silver towards carbon–halogen bond cleavage are evidenced by a positive shift in the reduction of acetochlor as compared to the more inert glassy carbon electrode. Voltammograms in the presence of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP), and comparisons of calculated relative interaction energies between acetochlor, possible intermediates, and deschloroacetochlor in the presence of different proton donors, suggest strong hydrogen-bonding interactions between HFIP and a carbanion intermediate. Addition of HFIP to electrolysis conditions promotes complete reduction at both cathode materials, with formation of deschloroacetochlor in high yields. In deuterium labelling studies, the use of DMF-d 7 led to no evidence for deuterium atom incorporation. However, when HFIP-OD or D2O were employed as a proton source, substantial amounts of deuterated deschloroacetochlor were observed. A mechanism for the reduction of acetochlor is proposed, in which radical intermediates do not play a significant role in reduction, rather a carbanion intermediate pathway is followed.

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Using silver cathodes for organic electrosynthesis and mechanistic studies

Cited by 16 publications

References 35 publications

Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene

Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene

A DFT and SERS study of synergistic roles of thermodynamics and kinetics during the electrocatalytic reduction of benzyl chloride at silver cathodes

Direct Electrochemical Reduction of Acetochlor at Carbon and Silver Cathodes in Dimethylformamide

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