Preface for the 67th Special Feature “Revolutionizing Synthetic Organic Chemistry by Electrosynthesis”

Naoki SHIDA; Eisuke SATO

doi:10.5796/electrochemistry.23-67113

Abstract

The 67th special feature, titled “Electrosynthesis Revolutionizing Synthetic Organic Chemistry,” will focus on electrosynthesis, an innovative technology with the potential for sustainable compound production. Electrosynthesis is a chemical process that uses electricity as the main driving force for reactions, replacing harmful chemicals with electrons. The topic spans both small- and macro-molecule synthesis and highlights the adaptability and promise of electrosynthesis in several areas. The emphasis on the importance of electrosynthesis in the area of green chemistry makes it of interest to professionals and academic researchers in the field of industrial chemistry. This special feature presents a path of change toward a more environmentally friendly, sustainable, and efficient chemical synthesis.

Achieving sustainable chemical processes has become an essential requirement of modern society. The chemical industry is currently facing a critical juncture as it grapples with pressing environmental issues and recognizes the limited availability of certain essential commodities. In response, electrosynthesis has emerged as an innovative and disruptive technology that presents a new way to produce chemical molecules in an environmentally friendly manner. Electrosynthesis is a field of study that focuses on the use of electricity as the primary driving force of chemical reactions. This approach is a significant departure from traditional chemical synthesis methods that rely on often hazardous oxidizing and reducing agents. The beauty of this technology lies in its inherent sustainability, which greatly reduces the impact of chemical synthesis on the environment.

Electrosynthesis presents a feasible option for producing valuable molecules in the realm of small molecule synthesis. The ability to precisely transform molecular structures, often with minimal waste and energy input, sets new standards for green chemistry that can be applied in a variety of fields, including pharmaceuticals, fine chemicals, and advanced materials. These characteristics accelerate the growing collaboration between electrochemistry and organic synthesis and offer promising prospects for the field of chemistry.

This journal, Electrochemistry, has made significant contributions in the field of electrosynthesis over the years, which has undoubtedly contributed to the renaissance period of the field we all currently witnessing as shown Table 1. Since 1999, special features on electrosynthesis have been organized twice by Organic Electrochemistry Group of the Electrochemical Society of Japan, entitled “Leading Edge in Organic Electrochemistry” issued in Volume 74, No. 8 in 2006 and “Organic Electrochemistry en route for a Greener Innovation” in Volume 81, No. 5 in 2013 with a substantial number of cross-disciplinary contributions.¹ As a time to change the paradigm of chemical synthesis for a sustainable future, the editorial team, young members from Organic Electrochemistry Group of the Electrochemical Society of Japan, arranged the 67th special feature, “Electrosynthesis Revolutionizing Synthetic Organic Chemistry” to cover a diverse range of state-of-the-art topics that demonstrate the depth and evolution of electrosynthesis.

Table 1. History of articles for organic electrochemistry in Journal “Electrochemistry” since 1999. For the convenience of readers, the same tables are included in J-STAGE as Supplementary material.

No.	Title	Vol.	Page	Year	DOI
1	Paired Electrosynthesis of Organic Compounds	67	4	1999	https://doi.org/10.5796/electrochemistry.67.4
2	Enantioselective Catalytic Oxidation of 1-Phenylethanol on a Chiral Nitroxyl Radical-Terminated Self-Assembled Monolayer Modified Electrode	67	900	1999	https://doi.org/10.5796/electrochemistry.67.900
3	Application of Ultrasound to Electrochemical Measurements and Analyses	67	912	1999	https://doi.org/10.5796/electrochemistry.67.912
4	Kolbe Electrolysis of Carboxylates on a Hydrophobic Platinum Electrode Composite-Plated with PTFE Particles	67	1042	1999	https://doi.org/10.5796/electrochemistry.67.1042
5	Ultrasonic Effects on Electroorganic Processes. XIII. A Role of Ultrasonic Cavitation in Electrooxidative Polymerization of Aniline	67	1114	1999	https://doi.org/10.5796/electrochemistry.67.1114
6	Surface Oxidation and Activation of Carbon Fiber Using Radical NO₃· Generated by Anodic Oxidation of NO₃⁻	67	1117	1999	https://doi.org/10.5796/electrochemistry.67.1117
7	Electrocatalytic Hydrogenation of Olefins Using Palladium Metal Microparticles Deposited on Viologen Film-Coated Graphite Felt	68	42	2000	https://doi.org/10.5796/electrochemistry.68.42
8	Ultrasonic Effects on Electroorganic Processes. XVIII. A Limiting Current Study on Indirect Electrooxidation of n-Butylamine with a Triarylamine Redox Mediator	68	262	2000	https://doi.org/10.5796/electrochemistry.68.262
9	Introduction of Sulfur Atoms into Trifluoromethylated Alkenyl Sulfones and Chlorides Using a Reactive Sulfur-Graphite Electrode	68	955	2000	https://doi.org/10.5796/electrochemistry.68.955
10	Ultrasonic Effects on Electroorganic Processes (19) Cathodic Reduction and Adsorption of p-Methylbenzaldehyde on a Liquid Mercury Electrode	69	10	2001	https://doi.org/10.5796/electrochemistry.69.10
11	Electroreductive Synthesis of Silylene-Germylene Copolymers with Ordered Sequences	72	159	2004	https://doi.org/10.5796/electrochemistry.72.159
12	Ultrasonic Effects on Electroorganic Processes. Part 26. Current Efficiency and Product Selectivity in the Anodic Cyanation of N-Methylpyrrole	72	821	2004	https://doi.org/10.5796/electrochemistry.72.821
13	Electrocatalytic Debromination of Organic Bromides Using a Cobalt(II)Salen Complex in Ionic Liquids.	72	849	2004	https://doi.org/10.5796/electrochemistry.72.849
14	Electroreductive Synthesis of Polysilanes Promoted by the Anodically Dissolved Magnesium Ion	73	419	2005	https://doi.org/10.5796/electrochemistry.73.419
15	Electroreduction of Methyl Cinnamate by Using Electrochemically Surface Modified Carbon Fiber Electrodes	74	216	2006	https://doi.org/10.5796/electrochemistry.74.216
16	Surface Modification of Carbon Fiber by Using Electro-Oxidation and -Reduction Sequential Procedure	74	226	2006	https://doi.org/10.5796/electrochemistry.74.226
17	Organic Electrochemistry: Advancing the Science of Reactive Intermediates and Controlled Chemical Processes	74	583	2006	https://doi.org/10.5796/electrochemistry.74.583
18	Vision in Special Issue for “Leading Edge in Organic Electrochemistry”	74	584	2006	https://doi.org/10.5796/electrochemistry.74.584
19	Development of New Methodologies toward Green Sustainable Organic Electrode Processes	74	585	2006	https://doi.org/10.5796/electrochemistry.74.585
20	Electrochemical Synthesis of Polyphenylene in a Centrifugal Field	74	590	2006	https://doi.org/10.5796/electrochemistry.74.590
21	Electrochemical Dechlorination of Chloroform on Single Crystal Electrodes of Silver in Acetonitrile	74	593	2006	https://doi.org/10.5796/electrochemistry.74.593
22	Preparation of Chiral Polypyrrole Film-Coated Electrode Incorporating Palladium Metal and Asymmetric Hydrogenation of α-Keto Esters	74	596	2006	https://doi.org/10.5796/electrochemistry.74.596
23	Electrolysis and Its Hybrid Methods Applied to Decomposition of Endocrine Disrupting Chemicals	74	599	2006	https://doi.org/10.5796/electrochemistry.74.599
24	Electroreductive Formation of Silyl Anion and Its Reaction with Electrophiles	74	603	2006	https://doi.org/10.5796/electrochemistry.74.603
25	Preparation and Potentiometric Measurement of Peroxycitric Acid	74	606	2006	https://doi.org/10.5796/electrochemistry.74.606
26	Oxidation of Mangostins, the Naturally Occurring Xanthone Derivatives Carrying Diverse Biological Activities	74	609	2006	https://doi.org/10.5796/electrochemistry.74.609
27	Electrochemical Carboxylation of Aliphatic Ketones: Synthesis of β-Keto Carboxylic Acids	74	612	2006	https://doi.org/10.5796/electrochemistry.74.612
28	Mixed-Kolbe Electrolysis Using Solid-Supported Bases	74	615	2006	https://doi.org/10.5796/electrochemistry.74.615
29	Development of a Novel Electrolytic System Using KBr as a Mediator and Solid-Supported Acids as a Supporting Electrolyte	74	618	2006	https://doi.org/10.5796/electrochemistry.74.618
30	Reversible Capture of Electrogenerated Intermediates by Liquefiable Micro-Particles Containing an Amphiphilic Tag	74	621	2006	https://doi.org/10.5796/electrochemistry.74.621
31	Cycloalkane-Based Thermomorphic Electrochemical Reaction System Composed of Nitrile-Solvents	74	625	2006	https://doi.org/10.5796/electrochemistry.74.625
32	Fabrication of an Electrochemical Sensor Array for 2D H₂O₂ Imaging	74	628	2006	https://doi.org/10.5796/electrochemistry.74.628
33	Oxidative Degradation of Aqueous Alkanesulfonates by Contact Glow Discharge Electrolysis	74	632	2006	https://doi.org/10.5796/electrochemistry.74.632
34	A Novel 1,4-Addition Type Reaction of β-Keto Esters with Vinyl Ketones Catalyzed by Iron(II)Tetrafluoroborate in an Ionic Liquid Solvent System	74	635	2006	https://doi.org/10.5796/electrochemistry.74.635
35	Electron Transfer Kinetics between PQQ-Dependent Soluble Glucose Dehydrogenase and Mediators	74	639	2006	https://doi.org/10.5796/electrochemistry.74.639
36	Electrochemical Quartz Crystal Microbalance Study of Direct Bioelectrocatalytic Reduction of Bilirubin Oxidase	74	642	2006	https://doi.org/10.5796/electrochemistry.74.642
37	Electrochemical Oxidation of L-Prolinol Derivative Protected with 1-Alkoxy-2,2,2-Trifluoroethyl Group	74	645	2006	https://doi.org/10.5796/electrochemistry.74.645
38	Reaction Analysis of 3-Substituted-Diphenylamine Cation Radicals in Acetonitrile. Cyclization Reaction vs. Benzidine Formation	74	649	2006	https://doi.org/10.5796/electrochemistry.74.649
39	Electrooxidative N-Halogenation of 2-Azetidinone Derivatives	74	656	2006	https://doi.org/10.5796/electrochemistry.74.656
40	Preparation of the Modified Platinum Electrodes Bearing the Alkali Metal Ion-Crown Ether Complexes as Mediatory Centers and Their Application to the Electroreduction of Methyl Decanoate	74	659	2006	https://doi.org/10.5796/electrochemistry.74.659
41	Electrochemical Synthesis of Poly (Cyclotetramethylenesilylene)	74	668	2006	https://doi.org/10.5796/electrochemistry.74.668
42	Electroauxiliary-Assisted Sequential Introduction of Organic Groups on the α-Carbons of Nitrogen	74	672	2006	https://doi.org/10.5796/electrochemistry.74.672
43	One-Pot Vicinal and Geminal Double Carboalkoxylation with N-Carboalkoxy-Imidazole by Electroreduction of Aromatic Vinyl and Imine Derivatives	74	680	2006	https://doi.org/10.5796/electrochemistry.74.680
44	Kinetics of Mono- and Dimethoxy-Substituted Benzyl Alcohol Oxidation by Phthalimido-N-Oxyl Radical	74	685	2006	https://doi.org/10.5796/electrochemistry.74.685
45	Phenylboronic Acid Monolayer-Modified Electrodes Sensitive to Ribonucleosides	74	688	2006	https://doi.org/10.5796/electrochemistry.74.688
46	Indirect Electroreduction of Imines and Diimines Using a Sacrificial Sulfur-Graphite Electrode	74	691	2006	https://doi.org/10.5796/electrochemistry.74.691
47	Electrochemical Deposition of Ni/SiC under Centrifugal Fields	76	824	2008	https://doi.org/10.5796/electrochemistry.76.824
48	Construction of Cycloalkane-Based Thermomorphic (CBT) Electrolyte Solution Systems and Application for Anodic Conversion of a Furan Derivative	76	874	2008	https://doi.org/10.5796/electrochemistry.76.874
49	Synthesis of Germane-Stannane Copolymers Using Electrochemically Generated Germyl Dianions	76	891	2008	https://doi.org/10.5796/electrochemistry.76.891
50	Highly Regioselective Anodic Monofluorination of 3H-1,4-Benzoxathian-2-Ones in Et₄NF·4HF/MeCN	76	896	2008	https://doi.org/10.5796/electrochemistry.76.896
51	Anodic Carbon-Carbon Bond Formation in Lithium Perchlorate/Nitromethane Electrolyte Solution	77	21	2009	https://doi.org/10.5796/electrochemistry.77.21
52	Design of Redox-Mediatory Systems for Electro-Organic Synthesis	77	1002	2009	https://doi.org/10.5796/electrochemistry.77.1002
53	Highly Stereo- and Regio-Selective Intramolecular Cyclization with Diastereoselective Asymmetric Induction by Electroreduction of Optically Active N-Alkenyl-2-Acylpyrrolidines	79	447	2011	https://doi.org/10.5796/electrochemistry.79.447
54	Electrochemical Carboxylation of Flavones: Facile Synthesis of Flavanone-2-Carboxylic Acids	79	862	2011	https://doi.org/10.5796/electrochemistry.79.862
55	Organic Electrochemistry: Casting a Wider Net	81	317	2013	https://doi.org/10.5796/electrochemistry.81.317
56	Future Directions of Organic Electrochemistry	81	318	2013	https://doi.org/10.5796/electrochemistry.81.318
57	Application of Electrochemically Generated Hypervalent Iodine Oxidant to Natural Products Synthesis	81	319	2013	https://doi.org/10.5796/electrochemistry.81.319
58	Development of Dye-Sensitized Solar Cells Based on D-π-A Pyridinium Dye without Carboxylic Acid Moiety as Anchoring Group	81	325	2013	https://doi.org/10.5796/electrochemistry.81.325
59	Electrochemical and Photoelectrochemical Behaviors of Polythiophene Nanowires Prepared by Templated Electrodeposition in Supercritical Fluids	81	328	2013	https://doi.org/10.5796/electrochemistry.81.328
60	Cyclic Voltammetric Studies on Electrocatalytic Intermolecular [2 + 2] Cycloaddition Reactions in Lithium Perchlorate/Nitromethane Electrolyte Solution	81	331	2013	https://doi.org/10.5796/electrochemistry.81.331
61	Morphological and Electrochemical Properties of 3,4-Substitued Polythiophene Films Prepared by Electrochemical Polymerization	81	334	2013	https://doi.org/10.5796/electrochemistry.81.334
62	Triarylamine-Conjugated Bis(Dipyrrinato)Zinc(II) Complexes: Impact of Triarylamine on Photochemical Property and Multi-Redox Reaction	81	337	2013	https://doi.org/10.5796/electrochemistry.81.337
63	From Thiopheneboroles to Boron-Containing Conjugated Macromolecules via Electropolymerization	81	340	2013	https://doi.org/10.5796/electrochemistry.81.340
64	Redox Properties of 2,3-Diaminophenazine and Its Electropolymerized Product in Aqueous and Acetonitrile Solutions	81	343	2013	https://doi.org/10.5796/electrochemistry.81.343
65	Recyclable Palladium Catalyst in PEG/CH₃CN Biphasic System for Electro-Oxidative Wacker-Type Reaction	81	347	2013	https://doi.org/10.5796/electrochemistry.81.347
66	Acceleration of Electroreduction Reaction of Water-Soluble Selenium Compounds in the Presence of Methyl Viologen	81	350	2013	https://doi.org/10.5796/electrochemistry.81.350
67	Anodic Alkoxylation of Lactams Followed by Reactions with Carbon Nucleophiles in a One-Pot Manner Using HFIP as a Solvent	81	353	2013	https://doi.org/10.5796/electrochemistry.81.353
68	Electro-Reductive Homo-Coupling Reaction of Aryl Bromides in PdCl₂(PPh₃)₂/Pyridinium Salt Double Mediatory Systems	81	356	2013	https://doi.org/10.5796/electrochemistry.81.356
69	Electroreduction of Aryl Halides Loaded on Palladium-Immobilized Activated Carbon	81	359	2013	https://doi.org/10.5796/electrochemistry.81.359
70	Electro-Reductive Halogen-Deuterium Exchange and Methylation of Aryl Halides in Acetonitrile	81	362	2013	https://doi.org/10.5796/electrochemistry.81.362
71	Sodium Salts Dissolution in an Aprotic Solvent by Coordination of Poly(Ethylene Glycol) for Effective Anodic Reactions of Organic Compounds	81	365	2013	https://doi.org/10.5796/electrochemistry.81.365
72	O-Carborane-Triphenylamine Dyad: Studies on Its Acceptor-Donor Behavior toward Dual Redox Mediator	81	368	2013	https://doi.org/10.5796/electrochemistry.81.368
73	An Electrolytic System Based on the Acid-Base Reaction between Solid-Supported Acids and Water	81	371	2013	https://doi.org/10.5796/electrochemistry.81.371
74	Electrochemical Oxidation of 1,2-Diols to α-Hydroxyketones in Water	81	374	2013	https://doi.org/10.5796/electrochemistry.81.374
75	Investigation of the Pathway for Intramolecular Electron Transfer in Anodic [2 + 2] Cycloaddition Reactions	81	377	2013	https://doi.org/10.5796/electrochemistry.81.377
76	Regioselective Electrochemical Carboxylation of Polyfluoroarenes	81	380	2013	https://doi.org/10.5796/electrochemistry.81.380
77	Preparation of Thermoresponsive Polymer-Modified Electrodes Having a TEMPO Moiety	81	383	2013	https://doi.org/10.5796/electrochemistry.81.383
78	Tuning of Electronic Properties of π-Conjugated Polymers Possessing 1,4-Mercapto-1,3-Butadiene-1,4-Diyl Units by Variation of Oxidation States of Sulfur Atoms	81	388	2013	https://doi.org/10.5796/electrochemistry.81.388
79	Anodic Cyanation of Arylsilanes without Elimination of Silyl Groups	81	394	2013	https://doi.org/10.5796/electrochemistry.81.394
80	Multiple Alkylation of Thiophene Derivatives with Simple and Extended Diarylcarbenium Ion Pools	81	399	2013	https://doi.org/10.5796/electrochemistry.81.399
81	Characteristics of Thin-Film Transistors Based on 2,8-Disubstituted Chrysene Derivatives with Polymer-Treated SiO₂ Dielectric Layers	81	402	2013	https://doi.org/10.5796/electrochemistry.81.402
82	Electro-Synthesis and Characterization of Polymer Nanostructures from Terthiophene Using Silica Mesoporous Films as Template	82	146	2014	https://doi.org/10.5796/electrochemistry.82.146
83	Esterification of Carboxylic Acids with Alkyl Halides Using Electroreduction	83	161	2015	https://doi.org/10.5796/electrochemistry.83.161
84	Development of Electroorganic Reactions Utilizing Stabilized Reactive Species and Its Application to Organic Energy Storage Materials	86	298	2018	https://doi.org/10.5796/electrochemistry.18-6-e2671
85	The Utilization of Boron-Doped Diamond Electrodes for the Electrochemical Reduction of CO₂: Toward the Production Compounds with a High Number of Carbon Atoms	87	109	2019	https://doi.org/10.5796/electrochemistry.19-h0001
86	Electro-Generated Acids Catalyzed Epoxyolefin Cyclizations via Cationic Chain Reactions	88	262	2020	https://doi.org/10.5796/electrochemistry.20-00032
87	Comparison of Electrosynthesis of Ammonium Persulfate by Membrane Electrolytic Cells with Shared Catholyte and with Separate Catholyte	88	268	2020	https://doi.org/10.5796/electrochemistry.18-00063
88	Intermolecular Carbon–Carbon Bond Formation Followed by Intramolecular Cyclization of Electrochemically Generated Magnesium Anthracenes and Esters in the Presence of Chlorotrimethylsilane	88	314	2020	https://doi.org/10.5796/electrochemistry.20-00012
89	Flow Electrosynthesis and Molecular Weight Control of Polyphenylene Deriving from 1,4-Bis(Trimethylsilyl)Benzene: Effect of a Silyl Substituent on the Coupling Position	88	336	2020	https://doi.org/10.5796/electrochemistry.20-00060
90	Redox-Neutral Radical-Cation Reactions: Multiple Carbon–Carbon Bond Formations Enabled by Single-Electron Transfer	88	497	2020	https://doi.org/10.5796/electrochemistry.20-00088
91	Bipolar Electrochemical Fluorination of Triphenylmethane and Bis(Phenylthio)Diphenylmethane Derivatives in a U-Shaped Cell	89	476	2021	https://doi.org/10.5796/electrochemistry.21-00074
92	Application of Boron-Doped Diamond Electrodes: Focusing on the Electrochemical Reduction of Carbon Dioxide	90	101002	2022	https://doi.org/10.5796/electrochemistry.22-00060
93	Electrosynthesis Governed by Electrolyte: Case Studies That Give Some Hints for the Rational Design of Electrolyte	90	101004	2022	https://doi.org/10.5796/electrochemistry.22-00074

We sincerely appreciate the authors and reviewers for their valuable contributions to this Special Feature. The editors are grateful for the two invited papers from the groups of Professor Shinobu Takizawa of Osaka University and Professor Tomoko Yajima of Ochanomizu University.²^,³ It is our hope that the information and perspectives presented in this special feature will serve as a catalyst for the continual progress of electrosynthesis and ultimately help establish a more environmentally friendly trajectory for the chemical industry.

Acknowledgment

We would like to thank the members of the Executive Committee of the Organic Electrochemistry Group of the Electrochemical Society of Japan, and the Editorial Board Member of Electrochemistry for their various advice in planning this special feature. This project was supported by the Electrochemistry Society of Japan for the burden of APC.

CRediT Authorship Contribution Statement

Naoki Shida: Writing – original draft (Lead), Writing – review & editing (Lead)

Eisuke Sato: Writing – review & editing (Lead)

Conflict of Interest

The authors declare no conflict of interest in the manuscript.

Footnotes

N. Shida and E. Sato: Equal Contribution

N. Shida and E. Sato: ECSJ Active Members

References

Biographies

Naoki Shida (Assistant Professor, Department of Chemistry and Life Science, Yokohama National University, YNU)

Naoki Shida received his B.S. degree from YNU. He then proceeded to the Ph.D. program at Tokyo Institute of Technology under the supervision of Prof. Shinsuke Inagi, which he completed in 2016. After working as JSPS PD at Tokyo University of Agriculture and Technology and Caltech, he started his academic career as a specially appointed assistant professor in Inagi group at Tokyo Tech in 2018. He then joined Prof. Atobe’s group at YNU in 2020.

Eisuke Sato (Assistant Professor, the Graduate School of Environmental, Life, Natural Science and Technology, Okayama University)

Eisuke Sato received his Ph. D degree in science from Keio University under the supervision of Prof. Kiyotake Suenaga in 2018. He received a postdoctoral fellowship from the Alexander von Humboldt Foundation and worked as a research fellow under the supervision of Prof. Till Opatz at Johannes Gutenberg University Mainz. In 2020, he joined the group of Prof. Seiji Suga as an assistant professor at Okayama University.

Corresponding author

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