Constant Potential and Constant Current Electrolysis: An Introduction and Comparison of Different Techniques for Organic Electrosynthesis

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(22), P. 15866 - 15874

Published: Sept. 21, 2021

Electrosynthesis involves transferring charge between two electrodes to promote chemical reactions by applying potential. The modes of controlling the current and potential can affect reaction mechanism, product distribution yields, add a control factor for optimization. In this Synopsis, theoretical discussion is applied specific case studies from literature illustrate methods adjusting tracking electrical parameters optimization monitoring electroorganic reactions.

Language: Английский

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Dehydrogenative Imination of Low-Valent Sulfur Compounds─Fast and Scalable Synthesis of Sulfilimines, Sulfinamidines, and Sulfinimidate Esters

JACS Au, Journal Year: 2023, Volume and Issue: 3(2), P. 575 - 583

Published: Feb. 7, 2023

Herein, we describe an electrochemical pathway for the synthesis of sulfilimines, sulfoximines, sulfinamidines, and sulfinimidate esters from readily available low-valent sulfur compounds primary amides or their analogues. The combination solvents supporting electrolytes together act both as electrolyte well a mediator, leading to efficient use reactants. Both can be easily recovered, enabling atom-efficient sustainable process. A broad scope with N-EWGs is accessed in up excellent yields functional group tolerance. This fast scaled multigram quantities high robustness fluctuation current densities 3 orders magnitude. sulfilimines are converted into corresponding sulfoximines ex-cell process using electro-generated peroxodicarbonate green oxidizer. Thereby, preparatively valuable NH accessible.

Language: Английский

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Selective Electrochemical Degradation of Lignosulfonate to Bio‐Based Aldehydes

ChemSusChem, Journal Year: 2023, Volume and Issue: 16(8)

Published: Jan. 18, 2023

A sustainable electrochemical pathway for degradation and thermal treatment of technical lignosulfonate is presented. This approach an opportunity to produce remarkable quantities low molecular weight compounds, such as vanillin acetovanillone. For the degradation, a simple two-electrode arrangement in aqueous media used, which also easily scalable. The oxidation biopolymer occurs at anode whereas hydrogen evolved cathode. subsequent supports robust chemical structure lignosulfonates. With optimized electrolytic conditions, could be obtained 9.7 wt% relative dry mass used. Aside from vanillin, by-products acetovanillone or vanillic acid were observed lower yields. new reliable one-pot, two-step different technically relevant lignosulfonates established with advantages using electrons oxidizing agent, results reagent waste.

Language: Английский

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Electrochemical Synthesis of Pyrazolines and Pyrazoles via [3+2] Dipolar Cycloaddition

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 62(9)

Published: Dec. 7, 2022

Pyrazolines and pyrazoles are common important motifs of pharmaceutical agents agrochemicals. Herein, the first electrochemical approach for their direct synthesis from easily accessible hydrazones dipolarophiles up to decagram scale is presented. The application a biphasic system (aqueous/organic) even allows conversion highly sensitive alkenes, wherein inexpensive sodium iodide employed in dual role as supporting electrolyte mediator. In addition, mechanistic insight into reaction given by isolation key step intermediates. relevance presented underlined commercial herbicide safener mefenpyr-diethyl good yields.

Language: Английский

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General Concepts and Recent Advances in the Electrochemical Transformation of Chloro‐ and Hydrosilanes

ChemElectroChem, Journal Year: 2023, Volume and Issue: 10(4)

Published: Jan. 23, 2023

Abstract Organosilanes play an important role in organic synthesis as well a variety of further areas, ranging from life science to transportation. Especially, the electrochemical access has become increasingly past years and developed into essential topic due new conceptual approaches mediated reaction control. With commercial availability high‐quality equipment, technical requirements for electro‐conversion are at hand wide audience. This results need concise survey silane transformation, appropriate novices experts alike. review provides overview most relevant work this field, identifies common obstacles working with chlorosilanes hydrosilanes bridges gap between known techniques novel methods respect their conversion. The historical development is outlined reference various cathodic anodic conversions should encourage expand research field transformation.

Language: Английский

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A guide to troubleshooting metal sacrificial anodes for organic electrosynthesis

Chemical Science, Journal Year: 2024, Volume and Issue: 15(16), P. 5814 - 5831

Published: Jan. 1, 2024

Sacrificial anodes enable reductive electrosynthesis but can inadvertently limit the conditions compatible with organic reactions. Addressing challenges that arise at sacrificial improve yields and streamline reaction optimization.

Language: Английский

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Bayesian optimization-driven parallel-screening of multiple parameters for the flow synthesis of biaryl compounds

Communications Chemistry, Journal Year: 2022, Volume and Issue: 5(1)

Published: Nov. 10, 2022

Abstract Traditional optimization methods using one variable at a time approach waste and chemicals assume that different parameters are independent from another. Hence, simpler, more practical, rapid process for predicting reaction conditions can be applied to several manufacturing environmentally sustainable processes is highly desirable. In this study, biaryl compounds were synthesized efficiently an organic Brønsted acid catalyst in flow system. Bayesian optimization-assisted multi-parameter screening, which employs one-hot encoding appropriate acquisition function, rapidly predicted the suitable synthesis of 2-amino-2′-hydroxy-biaryls (maximum yield 96%). The established protocol was also efficient 2,2′-dihydroxy biaryls (up 97% yield). optimized successfully gram-scale synthesis. We believe our algorithm beneficial as it screen reactor design without complicated quantification descriptors.

Language: Английский

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Working at the interfaces of data science and synthetic electrochemistry

Tetrahedron Chem, Journal Year: 2022, Volume and Issue: 1, P. 100012 - 100012

Published: March 1, 2022

Electrochemistry is quickly entering the mainstream of synthetic organic chemistry. The diversity new transformations enabled by electrochemistry to a large extent consequence unique features and reaction parameters in electrochemical systems including redox mediators, applied potential, electrode material, cell construction. While offering chemists means control reactivity selectivity, these additional also increase dimensionalities system complicate its optimization. This challenge, however, has spawned increasing adoption data science tools aid discovery as well development high-throughput screening platforms that facilitate generation high quality datasets. In this Perspective, we provide an overview recent advances data-science driven with emphasis on opportunities challenges facing growing subdiscipline.

Language: Английский

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Electrochemical synthesis of N,N′-disubstituted indazolin-3-ones via an intramolecular anodic dehydrogenative N–N coupling reaction

Chemical Science, Journal Year: 2022, Volume and Issue: 13(27), P. 8180 - 8186

Published: Jan. 1, 2022

A novel sustainable electrochemical synthetic route to N , ′-disubstituted indazolin-3-ones by direct anodic oxidation with mild reaction conditions, a simple galvanostatic setup, broad scope and excellent scalability is established.

Language: Английский

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The Oxidation of Organo‐Boron Compounds Using Electrochemically Generated Peroxodicarbonate

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(17)

Published: March 14, 2023

Abstract Peroxodicarbonate represents a green and largely underexplored oxidizer generated electrochemically from aqueous carbonate solutions. Through state‐of‐the‐art electrolyzer technology, highly concentrated solutions have now become accessible. These were successfully employed as in deborolative hydroxylations. A plethora of phenols alcohols thus been synthesized up to 99 % organoboron compounds using only non‐toxic solvents. This transformation was scaled‐up multi‐gram batch sizes.

Language: Английский

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