High-Throughput Electrochemistry: State of the Art, Challenges, and Perspective

[1]  D. Degner.  Organic electrosyntheses in industry , 1988 .

[2]  David J. Klauber,et al.  Electrochemical Deprotection of para-Methoxybenzyl Ethers in a Flow Electrolysis Cell. , 2017, Organic letters.

[3]  S. Waldvogel,et al.  Electrochemical Deoxygenation of Aromatic Amides and Sulfoxides , 2014 .

[4]  Tjark H. Meyer,et al.  Powering the Future: How Can Electrochemistry Make a Difference in Organic Synthesis? , 2020, Chem.

[5]  G. Gilardi,et al.  A new standardized electrochemical array for drug metabolic profiling with human cytochromes P450. , 2011, Analytical chemistry.

[6]  Richard J Ingham,et al.  Camera-enabled techniques for organic synthesis , 2013, Beilstein journal of organic chemistry.

[7]  Steven V Ley,et al.  Multistep synthesis using modular flow reactors: Bestmann-Ohira reagent for the formation of alkynes and triazoles. , 2009, Angewandte Chemie.

[8]  John D. Hayler,et al.  Key green chemistry research areas—a perspective from pharmaceutical manufacturers , 2007 .

[9]  Jun-ichi Yoshida,et al.  Modern strategies in electroorganic synthesis. , 2008, Chemical reviews.

[10]  Jason D. Williams,et al.  The Right Light: De Novo Design of a Robust Modular Photochemical Reactor for Optimum Batch and Flow Chemistry , 2019, ChemPhotoChem.

[11]  Steven V Ley,et al.  Fully automated continuous flow synthesis of 4,5-disubstituted oxazoles. , 2006, Organic letters.

[12]  G. Palleschi,et al.  Electrochemical immunosensor array using a 96-well screen-printed microplate for aflatoxin B1 detection. , 2007, Biosensors & bioelectronics.

[13]  Frank Glorius,et al.  A robustness screen for the rapid assessment of chemical reactions , 2013, Nature Chemistry.

[14]  Rongzhong Jiang.  Combinatorial electrochemical cell array for high throughput screening of micro-fuel-cells and metal/air batteries. , 2007, The Review of scientific instruments.

[15]  T. Wirth,et al.  Electroorganic Synthesis under Flow Conditions. , 2019, Accounts of chemical research.

[16]  Michael Shevlin,et al.  Practical High-Throughput Experimentation for Chemists , 2017, ACS medicinal chemistry letters.

[17]  W. Zhang,et al.  Electroreductive Carbofunctionalization of Alkenes with Alkyl Bromides via a Radical-Polar Crossover Mechanism. , 2020, Journal of the American Chemical Society.

[18]  Dieter Schollmeyer,et al.  Reagent- and Metal-Free Anodic C-C Cross-Coupling of Aniline Derivatives. , 2017, Angewandte Chemie.

[19]  S. Ludwigs,et al.  Water- and ionic-liquid-soluble branched polythiophenes bearing anionic and cationic moieties. , 2012, Journal of the American Chemical Society.

[20]  D. Pletcher,et al.  Flow Electrolysis Cells for the Synthetic Organic Chemistry Laboratory. , 2017, Chemical reviews.

[21]  Loïc J Blum,et al.  A 96-well electrochemical method for the screening of enzymatic activities. , 2013, Analytical chemistry.

[22]  S. Hilton,et al.  Supporting‐Electrolyte‐Free Electrochemical Methoxymethylation of Alcohols Using a 3D‐Printed Electrosynthesis Continuous Flow Cell System , 2019, ChemElectroChem.

[23]  T. Noël,et al.  Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride , 2019, Journal of the American Chemical Society.

[24]  Paul Richardson,et al.  A platform for automated nanomole-scale reaction screening and micromole-scale synthesis in flow , 2018, Science.

[25]  S. Waldvogel,et al.  Merging shuttle reactions and paired electrolysis for reversible vicinal dihalogenations , 2021, Science.

[26]  Guonan Chen,et al.  Electrochemiluminescence imaging-based high-throughput screening platform for electrocatalysts used in fuel cells. , 2012, Analytical chemistry.

[27]  Reddington,et al.  Combinatorial electrochemistry: A highly parallel, optical screening method for discovery of better electrocatalysts , 1998, Science.

[28]  Mohammad Mazloum-Ardakani,et al.  Screen-printed electrodes for biosensing: a review (2008–2013) , 2014, Microchimica Acta.

[29]  K. Moeller,et al.  Building addressable libraries: spatially isolated, chip-based reductive amination reactions. , 2006, Journal of the American Chemical Society.

[30]  Siegfried R. Waldvogel,et al.  Electrochemical Screening for Electroorganic Synthesis , 2016 .

[31]  C. Enke,et al.  Electrochemical processes in electrospray ionization mass spectrometry , 2000, Journal of mass spectrometry : JMS.

[32]  Nessa Carson.  Rise of the Robots. , 2020, Chemistry.

[33]  Virginie Mengeaud,et al.  A ceramic electrochemical microreactor for the methoxylation of methyl-2-furoate with direct mass spectrometry coupling. , 2002, Lab on a chip.

[34]  Steven V. Ley,et al.  A breakthrough method for the accurate addition of reagents in multi-step segmented flow processing† , 2011 .

[35]  Ulrich Simon,et al.  Workflow for High Throughput Screening of Gas Sensing Materials , 2006, Sensors (Basel, Switzerland).

[36]  K. Moeller.  Using Physical Organic Chemistry To Shape the Course of Electrochemical Reactions. , 2018, Chemical reviews.

[37]  Klavs F. Jensen,et al.  Development of a Photochemical Microfluidics Platform , 2011 .

[38]  Yu Kawamata,et al.  Synthetic Organic Electrochemistry: Calling All Engineers. , 2018, Angewandte Chemie.

[39]  M. Bradley,et al.  Polyethers: a solid-phase iterative approach. , 2001, Journal of combinatorial chemistry.

[40]  B. Speiser,et al.  Combinatorial micro electrochemistry. Part 4: Cyclic voltammetric redox screening of homogeneous ruthenium(II) hydrogenation catalysts☆ , 2005 .

[41]  Emory M Payne,et al.  A droplet microfluidic platform for high-throughput photochemical reaction discovery , 2020, Nature Communications.

[42]  Melda Sezen-Edmonds,et al.  Predicting Performance of Photochemical Transformations for Scaling Up in Different Platforms by Combining High-Throughput Experimentation with Computational Modeling , 2020 .

[43]  Yudin,et al.  Parallel electrosynthesis of alpha-alkoxycarbamates, alpha-alkoxyamides, and alpha-alkoxysulfonamides using the spatially addressable electrolysis platform (SAEP) , 2000, Journal of combinatorial chemistry.

[44]  Henkens,et al.  Multichannel Electrochemical Detection System for Quantitative Monitoring of PCR Amplification. , 1999, Clinical chemistry.

[45]  M. Matthews.  Green electrochemistry. Examples and challenges , 2001 .

[46]  V. Mirsky,et al.  Equipment for combinatorial electrochemical polymerization and high-throughput investigation of electrical properties of the synthesized polymers , 2004 .

[47]  E. Smotkin,et al.  High-throughput screening of fuel cell electrocatalysts ☆ , 2006 .

[48]  Shoichi Matsuda,et al.  High-throughput combinatorial screening of multi-component electrolyte additives to improve the performance of Li metal secondary batteries , 2019, Scientific Reports.

[49]  Christopher J. Welch,et al.  High throughput analysis enables high throughput experimentation in pharmaceutical process research , 2019, Reaction Chemistry & Engineering.

[50]  H. Girault,et al.  Coplanar interdigitated band electrodes for electrosynthesis , 1994 .

[51]  K. Moeller,et al.  Building addressable libraries: the use of electrochemistry for generating reactive Pd(II) reagents at preselected sites on a chip. , 2004, Journal of the American Chemical Society.

[52]  L. Blum,et al.  Innovative Electrochemical Screening Allows Transketolase Inhibitors to Be Identified. , 2018, Analytical chemistry.

[53]  Cian Kingston,et al.  A Survival Guide for the "Electro-curious". , 2019, Accounts of chemical research.

[54]  H. Uchida,et al.  Light‐Addressable Amperometric Sensor with Counter and Working Electrodes of the Same Material , 2021, IEEJ Transactions on Electrical and Electronic Engineering.

[55]  Scott A. Mauger,et al.  Use of a segmented cell for the combinatorial development of platinum group metal-free electrodes for polymer electrolyte fuel cells , 2020 .

[56]  David C. Leitch,et al.  The power and accessibility of high-throughput methods for catalysis research , 2019, Nature Catalysis.

[57]  Claudio Battilocchio,et al.  Enabling Technologies for the Future of Chemical Synthesis , 2016, ACS central science.

[58]  Y. Long,et al.  A novel screen-printed electrode array for rapid high-throughput detection. , 2012, The Analyst.

[59]  Phil S. Baran,et al.  Synthetic Organic Electrochemistry: An Enabling and Innately Sustainable Method , 2016, ACS central science.

[60]  Xin Yan,et al.  On-Demand Electrochemical Epoxidation in Nano-Electrospray Ionization Mass Spectrometry to Locate Carbon-Carbon Double Bonds. , 2020, Angewandte Chemie.

[61]  S. Waldvogel,et al.  Electroorganic synthesis of nitriles via a halogen-free domino oxidation-reduction sequence. , 2015, Chemical communications.

[62]  Fabrice Gallou,et al.  A Novel Cathode Material for Cathodic Dehalogenation of 1,1-Dibromo Cyclopropane Derivatives. , 2015, Chemistry.

[63]  Richard J Ingham,et al.  A Systems Approach towards an Intelligent and Self-Controlling Platform for Integrated Continuous Reaction Sequences** , 2014, Angewandte Chemie.

[64]  T. D. Hatchard,et al.  Design and Testing of a 64-Channel Combinatorial Electrochemical Cell , 2003 .

[65]  L. Blum,et al.  High‐Throughput Electrochemical Screening Assay for Free and Immobilized Oxidases: Electrochemiluminescence and Intermittent Pulse Amperometry , 2017 .

[66]  S. Ley,et al.  Enabling synthesis in fragment-based drug discovery by reactivity mapping: photoredox-mediated cross-dehydrogenative heteroarylation of cyclic amines† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c8sc04789h , 2018, Chemical science.

[67]  T. Wirth,et al.  An Easy‐to‐Machine Electrochemical Flow Microreactor: Efficient Synthesis of Isoindolinone and Flow Functionalization , 2017, Angewandte Chemie.

[68]  Xiaofeng Ma,et al.  Electrochemical methoxymethylation of alcohols - a new, green and safe approach for the preparation of MOM ethers and other acetals. , 2018, Chemical communications.

[69]  J. Lipkowski,et al.  Coadsorption of metal atoms and anions: Cu upd in the presence of SO42−, Cl− and Br− , 1995 .

[70]  David P. Hickey,et al.  Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry , 2019, Science.

[71]  G. V. Van Berkel,et al.  Derivatization for electrospray ionization mass spectrometry. 3. Electrochemically ionizable derivatives. , 1998, Analytical chemistry.

[72]  S. Waldvogel,et al.  Stabilizing Lead Cathodes with Diammonium Salt Additives in the Deoxygenation of Aromatic Amides , 2014 .

[73]  S. Waldvogel,et al.  Modern Electrochemical Aspects for the Synthesis of Value‐Added Organic Products , 2018, Angewandte Chemie.

[74]  F. Glorius,et al.  Rapid Assessment of the Reaction-Condition-Based Sensitivity of Chemical Transformations. , 2019, Angewandte Chemie.

[75]  C. Kappe,et al.  Translating batch electrochemistry to single-pass continuous flow conditions: an organic chemist’s guide , 2020, Journal of Flow Chemistry.

[76]  John R. Owen,et al.  High throughput screening of the effect of carbon coating in LiFePO4 electrodes , 2007 .

[77]  T. Noël,et al.  The Fundamentals Behind the Use of Flow Reactors in Electrochemistry , 2019, Accounts of chemical research.

[78]  Ling Li,et al.  The Evolution of High-Throughput Experimentation in Pharmaceutical Development and Perspectives on the Future , 2019, Organic Process Research & Development.

[79]  R. Potyrailo,et al.  Combinatorial and high-throughput development of sensing materials: the first 10 years. , 2008, Chemical reviews.

[80]  Manfred Kansy,et al.  High throughput solubility measurement in drug discovery and development. , 2007, Advanced drug delivery reviews.

[81]  S. Waldvogel,et al.  Highly Modular Flow Cell for Electroorganic Synthesis , 2017 .

[82]  S. Berritt,et al.  A Method for Identifying and Developing Functional Group Tolerant Catalytic Reactions: Application to the Buchwald-Hartwig Amination. , 2017, The Journal of organic chemistry.

[83]  Ulrich Simon,et al.  Design strategies for multielectrode arrays applicable for high-throughput impedance spectroscopy on novel gas sensor materials. , 2002, Journal of combinatorial chemistry.

[84]  S. Ley,et al.  Expedient preparation of nazlinine and a small library of indole alkaloids using flow electrochemistry as an enabling technology. , 2014, Organic letters.

[85]  M. Atobe,et al.  Applications of Flow Microreactors in Electrosynthetic Processes. , 2017, Chemical reviews.

[86]  P. Kebarle,et al.  Mechanism of electrospray mass spectrometry. Electrospray as an electrolysis cell , 1991 .

[87]  Robert J. Perkins,et al.  Electrochemical Nickel Catalysis for Sp2-Sp3 Cross-Electrophile Coupling Reactions of Unactivated Alkyl Halides. , 2017, Organic letters.

[88]  H. Beitollahi,et al.  Applications of electrochemical sensors and biosensors based on modified screen-printed electrodes: a review , 2020 .

[89]  Kevin E Bennet,et al.  Carbon nanofiber electrode array for electrochemical detection of dopamine using fast scan cyclic voltammetry. , 2011, The Analyst.

[90]  Jeffrey Y. Pan,et al.  Engineering Chemistry Innovation. , 2019, ACS medicinal chemistry letters.

[91]  Rachel Grainger,et al.  A Perspective on the Analytical Challenges Encountered in High-Throughput Experimentation , 2021 .

[92]  Anton Wiebe,et al.  Electrifying Organic Synthesis , 2018, Angewandte Chemie.

[93]  U. Schwaneberg,et al.  Coupling of electrochemical and optical measurements in a microtiter plate for the fast development of electro enzymatic processes with P450s , 2013 .

[94]  Christiane Schotten,et al.  Making electrochemistry easily accessible to the synthetic chemist , 2020, Green Chemistry.

[95]  U. Schwaneberg,et al.  An electrochemical microtiter plate for parallel spectroelectrochemical measurements , 2013 .

[96]  M. Ward,et al.  Automated electrochemical analysis with combinatorial electrode arrays. , 1999, Analytical chemistry.

[97]  Michael K. Wismer,et al.  Unlocking the Potential of High-Throughput Experimentation for Electrochemistry with a Standardized Microscale Reactor , 2021, ACS central science.

[98]  Johannes G. de Vries,et al.  The Power of High-Throughput Experimentation in Homogeneous Catalysis Research for Fine Chemicals , 2003 .

[99]  S. Ley,et al.  A Comment on Continuous Flow Technologies within the Agrochemical Industry , 2021 .

[100]  E. Steckhan,et al.  Environmental protection and economization of resources by electroorganic and electroenzymatic syntheses. , 2001, Chemosphere.

[101]  K. Chiba,et al.  Electrochemical Total Synthesis of Pyrrolophenanthridone Alkaloids: Controlling the Anodically Initiated Electron Transfer Process. , 2020, Organic letters.

[102]  Jason M. Stevens,et al.  High-Throughput Classical Chiral Resolution Screening of Synthetic Intermediates: Effects of Resolving Agents, Crystallization Solvents, and Other Factors , 2020 .

[103]  J. Kranendonk,et al.  A Scalable High-Throughput Deposition and Screening Setup Relevant to Industrial Electrocatalysis , 2020, Catalysts.

[104]  J. Janey,et al.  High-Throughput Extractions: A New Paradigm for Workup Optimization in Pharmaceutical Process Development , 2016 .

[105]  M. Rafiee,et al.  Electrochemical Oxidation of Alcohols and Aldehydes to Carboxylic Acids Catalyzed by 4-Acetamido-TEMPO: An Alternative to “Anelli” and “Pinnick” Oxidations , 2018, ACS Catalysis.

[106]  Sibel A Ozkan,et al.  A Review: New Trends in Electrode Systems for Sensitive Drug and Biomolecule Analysis , 2020, Critical reviews in analytical chemistry.

[107]  Allan S. Myerson,et al.  Polymorph Screening: Comparing a Semi-Automated Approach with a High Throughput Method , 2009 .

[108]  Rongzhong Jiang,et al.  A combinatorial approach toward electrochemical analysis , 2002 .

[109]  D. Schollmeyer,et al.  Source of Selectivity in Oxidative Cross-Coupling of Aryls by Solvent Effect of 1,1,1,3,3,3-Hexafluoropropan-2-ol. , 2015, Chemistry.

[110]  M. Kärkäs.  Electrochemical strategies for C-H functionalization and C-N bond formation. , 2018, Chemical Society reviews.

[111]  Wolfgang Märkle,et al.  Combinatorial micro electrochemistry: Part 1. Automated micro electrosynthesis of iminoquinol ether and [1,2,4]triazolo[4,3-a]pyridinium perchlorate collections in the wells of microtiter plates , 2005 .

[112]  Steven V Ley,et al.  Across‐the‐World Automated Optimization and Continuous‐Flow Synthesis of Pharmaceutical Agents Operating Through a Cloud‐Based Server , 2018, Angewandte Chemie.

[113]  L. Blum,et al.  Rapid electrochemical screening of NAD-dependent dehydrogenases in a 96-well format. , 2013, Chemical communications.

[114]  B. Speiser,et al.  Combinatorial micro-electrochemistry. Part 5. Electrosynthesis screening of the electroreductive coupling of α,β-unsaturated esters and allyl bromides in a room temperature ionic liquid , 2009 .

[115]  John D. Hayler,et al.  Key Green Chemistry research areas from a pharmaceutical manufacturers’ perspective revisited , 2018 .

[116]  Anirudh M. K. Nambiar,et al.  A multifunctional microfluidic platform for high-throughput experimentation of electroorganic chemistry. , 2020, Angewandte Chemie.

[117]  A. Erlenkötter,et al.  Flexible amperometric transducers for biosensors based on a screen printed three electrode system , 2000 .

[118]  Dieter Schollmeyer,et al.  Metal- and reagent-free highly selective anodic cross-coupling reaction of phenols. , 2014, Angewandte Chemie.

[119]  Thierry Ollevier,et al.  Bridging Lab and Industry with Flow Electrochemistry , 2020, iScience.

[120]  S. C. Perry,et al.  Review—The Design, Performance and Continuing Development of Electrochemical Reactors for Clean Electrosynthesis , 2020 .