Oxford University Press (OUP) Acta Medica Okayama 0009-2673 99 6 2026 Synthesis of boranils by iodide-mediated demethylative borylation and their properties uoag070 EN Koichi Mitsudo Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Ryo Magata Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Eisuke Sato Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Tomoya Nakamura Institute for Chemical Research, Kyoto University Atsushi Wakamiya Institute for Chemical Research, Kyoto University Seiji Suga Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Boranils, difluoroboron complexes with imine and phenoxy moieties, were synthesized by iodide-promoted demethylative borylation. The use of appropriate amounts of BF3•OEt2, Bu4NI, and Et3N enabled the highly efficient synthesis of boranils. Boranils containing heteroaromatics and highly π-extended boranils were also readily obtained by this method. Their physical properties were studied, and the properties were consistent with those calculated by DFT calculations. No potential conflict of interest relevant to this article was reported.

MDPI AG Acta Medica Okayama 2079-6447 5 2 2026 Solution-Processable Near-Infrared-Absorbing Dye: Thiophene-Substituted N-Phenylphenothiazine Radical Cations for Stable Thin Films 14 EN Masafumi Yano Faculty of Chemistry, Material and Bioengineering, Kansai University Kengo Sakai Faculty of Chemistry, Material and Bioengineering, Kansai University Minami Ueda Faculty of Chemistry, Material and Bioengineering, Kansai University Koichi Mitsudo Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Yukiyasu Kashiwagi Osaka Research Institute of Industrial Science and Technology We report a π-extended N-phenylphenothiazine dye bearing thiophene substituents, designed to address the practical compromise between long-wavelength near-infrared (NIR) absorption and the isolability of a stable radical cation state. The target compound was synthesized via Suzuki–Miyaura cross-coupling and exhibited good solubility in common organic solvents. Cyclic voltammetry in dichloromethane showed a reversible one-electron oxidation at E0 = 0.19 V vs. Fc/Fc+. Chemical oxidation afforded the corresponding radical cation, which showed an intense NIR absorption maximum at 910 nm. DFT calculations support thiophene-induced narrowing of the HOMO–SOMO gap and predict a pronounced bathochromic shift of the main absorption band. The radical cation was isolated as a stable PF6− salt and readily processed into spin-coated films, which retained strong NIR absorption and remained stable for months under ambient conditions. No potential conflict of interest relevant to this article was reported.

Wiley Acta Medica Okayama 2196-0216 13 8 2026 Electrochemical Synthesis of Benzo[b]Phosphole Oxides via Dehydrogenative Annulation Using 1,4-Diazabicyclo [2.2.2]Octane as a Mediator e70175 EN Koichi Mitsudo Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Sakura Kinjo Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Yasuyuki Okumura Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Eisuke Sato Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Riki Kato Research Institute for Interdisciplinary Science, Okayama University Yuta Nishina Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Seiji Suga Graduate School of Environmental, Life, Natural Science and Technology, Okayama University The electrochemical intermolecular annulation of diarylphosphine oxides with alkynes for the synthesis of benzo[b]phosphole oxides has been reported. The reaction proceeded under transition-metal- and oxidant-free conditions via indirect electrolysis, using 1,4-diazabicyclo[2.2.2]octane as a mediator. High-surface-area carbon electrodes, such as carbon felt and reticulated vitreous carbon, are essential for this reaction. Several diarylphosphine oxides and alkynes were applied to electrochemical annulation, and the corresponding benzo[b]phosphole oxides were obtained. Mechanistic studies suggested that the reaction proceeds via radical intermediates generated through multiple pathways. No potential conflict of interest relevant to this article was reported.

Wiley Acta Medica Okayama 1434-193X 2026 Informatics‐Driven and Automated Optimization in Flow Electrochemical Synthesis e202501237 EN Eisuke Sato Department of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Akine Tani Department of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Tomohiro Nakahama Department of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Koichi Mitsudo Department of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Seiji Suga Department of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Electrochemical synthesis has emerged as a powerful platform for environmentally sustainable chemical transformations. When integrated with flow chemistry, electrosynthetic processes exhibit enhanced scalability, making them suitable for industrial applications. Recently, the integration of electrochemical flow systems with informatics techniques has accelerated the optimization of reaction conditions. Data-driven strategies facilitate rapid exploration of multidimensional parameter spaces, enabling identification of optimal reaction conditions with high efficiency. These advances have enabled the development of automated optimization systems. This review highlights recent progress in combining electrosynthesis, flow chemistry, and computational tools, focusing on representative examples that illustrate efficient optimization protocols and autonomous reaction development. By showcasing these developments, we discuss how the integration of these technologies is driving innovation in electrochemical synthesis. No potential conflict of interest relevant to this article was reported.

International Union of Crystallography (IUCr) Acta Medica Okayama 2056-9890 82 2 2026 Crystal structure of tris[4-(3,4-dimethoxythiophen-2-yl)phenyl]amine E82 EN Masafumi Yano Kansai University Yukiyasu Kashiwagi Osaka Research Institute of Industrial Science and Technology Koki Oishi Kansai University Minori Yano Kansai University Koichi Mitsudo Okayama University In the title compound tris­[4-(3,4-di­meth­oxy­thio­phen-2-yl)phen­yl]amine (DMOT-TPA), C36H33NO6S3, the central nitro­gen atom shows no pyramidalization, with the three para-phenyl­ene rings arranged in a propeller-like geometry. Each thio­phene ring is twisted by about 25–29° relative to the adjacent phenyl­ene ring, giving a distorted π-conjugated framework. In the crystal, mol­ecules are linked through multiple C—H⋯π inter­actions into two-dimensional sheets, which extend into a three-dimensional network. A Cambridge Structural Database survey revealed no prior examples of tri­phenyl­amines bearing 3,4-di­meth­oxy­thio­phen units at the para positions. This unique structure provides new insights into the design of redox-active organic materials. No potential conflict of interest relevant to this article was reported.

Springer Science and Business Media LLC Acta Medica Okayama 2399-3669 8 1 2025 Synthesis of thienoacenes by electrochemical double C–S cyclization using a halogen mediator 366 EN Koichi Mitsudo Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Takuya Nagahara Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Nozomi Kataura Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Yuka Okamura Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Toki Yonezawa Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Yuri Tachibana Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Nolan Soulié Faculty of Science and Engineering, Sorbonne Université Keisuke Shigemori Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Eisuke Sato Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Hiroki Mandai Department of Pharmacy, Faculty of Pharmacy, Gifu University of Medical Science Seiji Suga Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Thienoacenes are significant compounds as organic materials. One of the most efficient ways to synthesize thienoacenes is to form multiple C–S bonds in a single step. Because unprotected S–H bonds are easily oxidized to S–S bonds, S-Me protected substrates are commonly used for the purpose. However, their reactivity is insufficient, and one-step construction of multiple C–S bonds is still challenging. We herein report the electrochemical synthesis of thienoacenes from S-methoxymethyl (MOM)-protected diarylacetylenes. In the presence of Bu4NBr as a halogen mediator, electrochemical double C–S cyclization of diarylacetylenes bearing two MOM groups proceeded to afford [1]benzothieno[3,2-b][1]benzothiophene (BTBT) derivatives. While S-Me or S-p-methoxybenzyl (PMB)-protected diarylacetylenes did not afford BTBT, BTBT was selectively obtained when a substrate protected with S-MOM groups was used. The S-MOM protection strategy is also effective for the electrochemical synthesis of a more π-expanded thienoacene such as dibenzo[d,d′]thieno[3,2-b,4,5-b′]dithiophene (DBTDT). No potential conflict of interest relevant to this article was reported.

MDPI AG Acta Medica Okayama 2079-6447 3 4 2024 N-Phenylphenothiazine Radical Cation with Extended π-Systems: Enhanced Heat Resistance of Triarylamine Radical Cations as Near-Infrared Absorbing Dyes 350 359 EN Masafumi Yano Faculty of Chemistry, Material and Bioengineering, Kansai University Minami Ueda Faculty of Chemistry, Material and Bioengineering, Kansai University Tatsuo Yajima Faculty of Chemistry, Material and Bioengineering, Kansai University Koichi Mitsudo Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Yukiyasu Kashiwagi Osaka Research Institute of Industrial Science and Technology N-Phenylphenothiazine derivatives extended with various aryl groups were designed and synthesized. These derivatives have bent conformation in crystal and exhibit high solubility. Radical cations obtained by one-electron oxidation of these derivatives gave stable radical cations in solution and showed absorption in the near-infrared region. A radical cation was isolated as a stable salt, which exhibited heat resistance up to around 200 °C. A design strategy for radical cation-based near-infrared absorbing dyes, which are easily oxidized and stable not only as a solution but in solid form, is described. No potential conflict of interest relevant to this article was reported.

American Chemical Society (ACS) Acta Medica Okayama 2691-3704 2025 Electrochemical Generation of Sulfonamidyl Radicals via Anodic Oxidation of Hydrogen Bonding Complexes: Applications to Electrosynthesis of Benzosultams EN Yasuyuki Okumura Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Eisuke Sato Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Koichi Mitsudo Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Seiji Suga Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Amidyl radicals and sulfonamidyl radicals are widely used in the field of organic synthesis. In particular, the electrochemical oxidation of amides in the presence of bases is one of the most practical methods for generating amidyl radicals. However, it is often difficult to observe the “true” radical precursor, such as an amide anion and/or a hydrogen bonding complex with an amide and a base. We found that a sulfonamide and Bu4NOAc form a 1:1 hydrogen bonding complex by spectroscopic experiments. Cyclic voltammetry suggested that 1:1 hydrogen bonding complexes should be oxidized predominantly under the optimized conditions to afford a sulfonamidyl radical via the proton-coupled electron transfer (PCET) process by the oxidation of the complex. Thus-generated sulfonamidyl radicals could be used in the electrochemical synthesis of a variety of benzosultams. No potential conflict of interest relevant to this article was reported.

American Chemical Society (ACS) Acta Medica Okayama 1523-7060 2025 Transformation of α,β-Unsaturated Aldehydes with a Small Amount of Electricity: Cyanosilylation, Isomerization, and Nucleophilic Addition EN Mayu Fujii Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Nanaho Ueno Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Koichi Mitsudo Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Eisuke Sato Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Seiji Suga Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University An electrochemical method was developed to convert α,β-unsaturated aldehydes into carboxylic acid derivatives via cyanosilylation, isomerization, and nucleophilic addition. This reaction is more sustainable than the usual electrochemical organic reaction because this reaction proceeds catalytically with active species generated by a very small amount of electricity. Furthermore, scale-up synthesis with a flow reactor has been achieved. No potential conflict of interest relevant to this article was reported.

American Chemical Society (ACS) Acta Medica Okayama 1523-7060 26 51 2024 Electrogenerated Lewis Acid-Catalyzed Claisen Rearrangement of Allyl Aryl Ethers 11111 11116 EN Yuta Niki Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Koichi Mitsudo Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Eisuke Sato Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Seiji Suga Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Catalysts for Claisen rearrangement have been intensively studied to overcome the need for high temperature. However, previous studies have encountered challenges, such as the need for heating, a long reaction time, and/or the need for equivalent amounts of catalyst. In this study, we introduce an effective electrogenerated boron-based Lewis acid catalyst for the aromatic Claisen rearrangement, which proceeds in a few minutes at ambient temperature. Generation of the electrogenerated Lewis acid catalyst is discussed based on NMR analysis and DFT calculations. No potential conflict of interest relevant to this article was reported.

Oxford University Press (OUP) Acta Medica Okayama 0366-7022 53 11 2024 SNAr hexafluoroisopropoxylation of electron-rich aryl fluoride with a catalytic electrical input upae196 EN Eisuke Sato Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Tomohiro Nakahama Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Koichi Mitsudo Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Seiji Suga Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Anodic oxidation–promoted SNAr reactions of electron-rich aryl fluoride were developed. The anodic oxidation of 4-fluoroanisole in hexafluoroisopropyl alcohol (HFIP) with K2CO3 led to SNAr-type hexafluoroisopropoxylation, and the reaction was completed with a catalytic electrical input. The results of cyclic voltammetry suggest that the radical cation of 4-fluoroanisole, which would react with the alkoxide of HFIP, is generated. Electron transfer between the intermediate and the starting material constructs the catalytic cycle, and the elimination of fluoride from the Meisenheimer complex produces the desired compound. No potential conflict of interest relevant to this article was reported.

Oxford University Press (OUP) Acta Medica Okayama 0366-7022 53 8 2024 Electrochemical synthesis of heterocyclic compounds via carbon–heteroatom bond formation: direct and indirect electrolysis upae146 EN Yasuyuki Okumura Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Eisuke Sato Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Koichi Mitsudo Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Seiji Suga Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Electrochemical organic synthesis has attracted attention as an environmentally friendly method for constructing heterocyclic compounds via carbon–heteroatom bond formation. Herein, we describe the representative examples of electrochemical reactions to produce heterocycles and discuss them according to whether they involve direct or indirect electrolysis. No potential conflict of interest relevant to this article was reported.

Beilstein-Institut Acta Medica Okayama 1860-5397 20 2024 Electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines under mild conditions with a proton-exchange membrane reactor 1560 1571 EN Koichi Mitsudo Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Atsushi Osaki Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Haruka Inoue Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Eisuke Sato Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Naoki Shida Graduate School of Engineering Science and Advanced Chemical Energy Research Center, Yokohama National University Mahito Atobe Graduate School of Engineering Science and Advanced Chemical Energy Research Center, Yokohama National University Seiji Suga Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University An electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines using a proton-exchange membrane (PEM) reactor was developed. Cyanoarenes were then reduced to the corresponding benzylamines at room temperature in the presence of ethyl phosphate. The reduction of nitroarenes proceeded at room temperature, and a variety of anilines were obtained. The quinoline reduction was efficiently promoted by adding a catalytic amount of p-toluenesulfonic acid (PTSA) or pyridinium p-toluenesulfonate (PPTS). Pyridine was also reduced to piperidine in the presence of PTSA. No potential conflict of interest relevant to this article was reported.

Georg Thieme Verlag KG Acta Medica Okayama 0039-7881 56 16 2024 Sequential Paired Electrochemical Transformation of Styrene Oxide via Anodic Meinwald Rearrangement and Cathodic Nitro­methylation in an Electrochemical Flow Reactor with Catalytic Electrical Input 2507 2512 EN Eisuke Sato Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Seiji Suga Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Kanon Nagamine Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Chika Sasaki Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Shumpei Kunimoto Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Koichi Mitsudo Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Paired electrosynthesis, which utilize both anodic and cathodic events in electrolysis, enables attractive transformations with higher current efficiency than conventional electrosynthesis. The electrochemical flow technique has been widely employed to ensure stable reaction conditions and mitigate issues stemming from mass transfer. In this study, the electrochemical Meinwald rearrangement of styrene oxides was investigated, yielding aldehydes as intermediates, followed by the nitromethylation of aldehydes to produce β-nitro alcohols. These reactions were achieved with catalytic electrical input, enabling the conversion of various styrene oxides into the corresponding β-nitro alcohols. No potential conflict of interest relevant to this article was reported.

Electrochemical Society of Japan Acta Medica Okayama 1344-3542 91 11 2023 Cathodic N-O Bond Cleavage of N-Alkoxy Amide 112005 EN Eisuke Sato Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Sayaka Ogita Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Koichi Mitsudo Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Seiji Suga Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Cathodic reduction efficiently cleaved N-O bonds. The simple cathodic reduction of Weinreb amides in a divided cell afforded the corresponding amide in good yields. Cyclic voltammetry experiments and density functional theory calculations suggested that the direct reduction of the N-methoxy amide generates the methoxy radical and amide anion. The release of methanol derived from methoxy radical would be the driving force of the N-O bond cleavage. No potential conflict of interest relevant to this article was reported.

Electrochemical Society of Japan Acta Medica Okayama 1344-3542 91 11 2023 Electrochemical Synthesis of Dibenzothiophene S,S-Dioxides from Biaryl Sulfonyl Hydrazides 112007 EN Yasuyuki Okumura Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Eisuke Sato Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Koichi Mitsudo Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Seiji Suga Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University The electrochemical synthesis of dibenzothiophene S,S-dioxides was achieved by the anodic oxidation of biaryl sulfonyl hydrazides. The use of Bu4NOTf as the electrolyte in HFIP/CH3NO2 (15 : 1) is essential. Several biaryl sulfonyl hydrazides followed by dibenzothiophene S,S-dioxides under mild electrochemical conditions. Control experiments and density functional theory calculations suggested that the electrooxidation of biaryl sulfonyl hydrazides would generate sulfonyl radicals or sulfonyl cations which were converted to dibenzothiophene S,S-dioxides. No potential conflict of interest relevant to this article was reported.

Wiley Acta Medica Okayama 2196-0216 11 1 2023 Alkynylation of Aldehydes Initiated by Cathodic Reduction e202300499 EN Eisuke Sato Division of Applied Chemistry Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Mayu Fujii Division of Applied Chemistry Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Koichi Mitsudo Division of Applied Chemistry Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Seiji Suga Division of Applied Chemistry Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Alkynylation of aldehydes initiated by cathodic reduction was performed. The cathodic alkynylation required only a semi-catalytic amount of electricity to consume the starting material completely. Cyclic voltammetry and some control experiments suggest that the electron-generated base derived from the cathodic reduction of benzaldehyde promotes alkynylation. No potential conflict of interest relevant to this article was reported.

Wiley Acta Medica Okayama 1434-193X 26 47 2023 Electrochemical Coupling Reactions Using Non‐Transition Metal Mediators: Recent Advances e202300835 EN Koichi Mitsudo Division of Applied Chemistry Graduate School of Environmental Life, Natural Science and Technology, Okayama University Yasuyuki Okumura Division of Applied Chemistry Graduate School of Environmental Life, Natural Science and Technology, Okayama University Eisuke Sato Division of Applied Chemistry Graduate School of Environmental Life, Natural Science and Technology, Okayama University Seiji Suga Division of Applied Chemistry Graduate School of Environmental Life, Natural Science and Technology, Okayama University Indirect electrolysis method using appropriate mediators enables numerous chemical reactions. The general principles of mediators were described herein with a particular focus on non-transition metal mediators. Recent representative examples of bond formation reactions by indirect electrolysis are summarized and discussed here. No potential conflict of interest relevant to this article was reported.

Beilstein-Institut Acta Medica Okayama 1860-5397 18 2022 Electrochemical hydrogenation of enones using a proton- exchange membrane reactor: selectivity and utility 1055 1061 EN Koichi Mitsudo Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Haruka Inoue Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Yuta Niki Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Eisuke Sato Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Seiji Suga Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Electrochemical hydrogenation of enones using a proton-exchange membrane reactor is described. The reduction of enones proceeded smoothly under mild conditions to afford ketones or alcohols. The reaction occurred chemoselectively with the use of different cathode catalysts (Pd/C or Ir/C). No potential conflict of interest relevant to this article was reported.

American Chemical Society (ACS) Acta Medica Okayama 1523-7060 23 8 2021 Electrosynthesis of Phosphacycles via Dehydrogenative C–P Bond Formation Using DABCO as a Mediator 3120 3124 EN Yuji Kurimoto Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Jun Yamashita Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Koichi Mitsudo Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Eisuke Sato Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Seiji Suga Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University The first electrochemical synthesis of diarylphosphole oxides (DPOs) was achieved under mild conditions. The practical protocol employs commercially available and inexpensive DABCO as a hydrogen atom transfer (HAT) mediator, leading to various DPOs in moderate to good yields. This procedure can also be applied to the synthesis of six-membered phosphacycles, such as phenophosphazine derivatives. Mechanistic studies suggested that the reaction proceeds via an electro-generated phosphinyl radical. No potential conflict of interest relevant to this article was reported.

Thieme Gruppe Acta Medica Okayama 0936-5214 31 19 2020 Integrated Synthesis of Thienyl Thioethers and Thieno[3,2-b]thiophenes via 1-Benzothiophen-3(2H)-ones 1947 1952 EN Koichi Mitsudo Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Nanae Habara Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Yoshiak Kobashi Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Yuji Kurimoto Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Hiroki Mandai Department of Pharmacy, Faculty of Pharmacy, Gifu University of Medical Science Seiji Suga Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University A one-pot procedure for the synthesis of thienyl thioethers is described. Several thienyl thioethers were synthesized by a TfOH-promoted Friedel–Crafts-type cyclization, a subsequent nucleophilic attack by an arenethiol, and dehydration. This protocol was successfully applied to the synthesis of thienoacene derivatives by using a Pd-catalyzed dehydrogenative cyclization. No potential conflict of interest relevant to this article was reported.

Wiley Acta Medica Okayama 1433-7851 59 20 2020 Electrochemical Synthesis of Thienoacene Derivatives: Transition‐Metal‐Free Dehydrogenative C−S Coupling Promoted by a Halogen Mediator 7803 7807 EN Koichi Mitsudo Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Ren Matsuo Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Toki Yonezawa Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Haruka Inoue Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Hiroki Mandai Department of Medical Technology, Gifu University of Medical Science Seiji Suga Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University The first electrochemical dehydrogenative C−S bond formation leading to thienoacene derivatives is described. Several thienoacene derivatives were synthesized by dehydrogenative C−H/S−H coupling. The addition of nBu4NBr, which catalytically promoted the reaction as a halogen mediator, was essential. No potential conflict of interest relevant to this article was reported.

American Chemical Society Acta Medica Okayama 15237060 20 22 2018 Synthesis and Properties of Dithieno-Fused 1,4-Azaborine Derivatives. 7336 7340 EN Koichi Mitsudo Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Keisuke Shigemori Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Hiroki Mandai Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Atsushi Wakamiya Institute for Chemical Research, Kyoto University Seiji Suga Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University The first synthesis of dithieno[3,2- b:2',3'- e][1,4]azaborinine (DTAB) derivatives has been achieved by Buchwald-Hartwig coupling and subsequent Friedel-Crafts-type C-H borylation. A facile method for further π-extension of DTAB was also developed via stannylation and subsequent Kosugi-Migita-Stille cross-coupling reaction. The fundamental properties of DTAB derivatives were also investigated. No potential conflict of interest relevant to this article was reported.

American Chemical Society Acta Medica Okayama 15237060 19 11 2017 Synthesis of 3-Benzo[b]thienyl 3-Thienyl Ether via an Addition-Elimination Reaction and Its Transformation to an Oxygen-Fused Dithiophene Skeleton: Synthesis and Properties of Benzodithienofuran and Its π-Extended Derivatives 2821 2824 EN Koichi Mitsudo Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Yuji Kurimoto Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Hiroki Mandai Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Seiji Suga Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University The synthesis of 3-benzo[b]thienyl 3-thienyl ether and its dehydrogenative cyclization leading to benzodithienofuran (BDTF; [1]benzothieno[3,2-b]thieno[2,3-d]furan) are described for the first time. Further transformation of BDTF to more π-extended BDTF derivatives and their fundamental physical properties are also studied. No potential conflict of interest relevant to this article was reported.

Chemical Society of Japan Acta Medica Okayama 03667022 47 8 2018 Cu/Fe/O=PPh3-Catalyzed Etherification for the Synthesis of Aryl 3-Benzo[b]thienyl Ethers 1044 1047 EN Koichi Mitsudo Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Takuya Asada Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Tomohiro Inada Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Yuji Kurimoto Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Hiroki Mandai Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Seiji Suga Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Cu/Fe-cocatalyzed cross-coupling reactions between 3-bromobenzo[b]thiophene and hydroxyaryls are described herein. The combination of Cu and Fe catalysts is important for the progress of the reactions, and the use of triphenylphosphine oxide as a ligand suppresses the dehalogenation of 3-bromobenzo[b]thiophene, and promptly facilitates the reaction. The obtained aryl benzo[b]thienyl ethers can be converted to pextended thienobenzofuran derivatives via Pd-catalyzed dehydrogenative cyclizations. No potential conflict of interest relevant to this article was reported.

GEORG THIEME Acta Medica Okayama 09365214 30 10 2019 1,10-Phenanthroline- or Electron-Promoted Cyanation of Aryl Iodides 1209 1214 EN Koichi Mitsudo Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Kazuki Yoshioka Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Takayuki Hirata Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Hiroki Mandai Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Koji Midorikawa Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Seiji Suga Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University A 1,10-phenanthroline-promoted cyanation of aryl iodides has been developed. 1,10-Phenanthroline worked as an organocatalyst for the reaction of aryl iodides with tetraalkylammonium cyanide to afford aryl cyanides. A similar reaction occurred through an electroreductive process. No potential conflict of interest relevant to this article was reported.

American Chemical Society Acta Medica Okayama 15237060 21 7 2019 Iodide-Mediated or Iodide-Catalyzed Demethylation and Friedel-Crafts C-H Borylative Cyclization Leading to Thiophene-Fused 1,2-Oxaborine Derivatives 2171 2175 EN Keisuke Shigemori Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Momoka Watanabe Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Julie Kong Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Koichi Mitsudo Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Atsushi Wakamiya Institute for Chemical Research, Kyoto University Hiroki Mandai Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Seiji Suga Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University The first synthesis of dithieno-1,2-oxaborine derivatives was achieved via iodide-mediated or iodide-catalyzed demethylation of 3-methoxy-2,2'-bithiophene and subsequent C-H borylation. A wide variety of thiophene-fused oxaborines could be synthesized by the procedure. No potential conflict of interest relevant to this article was reported.

Royal Society of Chemistry Acta Medica Okayama 1359-7345 46 48 2010 Electrochemical generation of silver acetylides from terminal alkynes with a Ag anode and integration into sequential Pd-catalysed coupling with arylboronic acids 9256 9258 EN Koichi Mitsudo Takuya Shiraga Jun-ichi Mizukawa Seiji Suga Hideo Tanaka An electro-oxidative method for generating silver acetylides from acetylenes with a Ag anode was developed. The reaction could be integrated into a Pd-catalysed electrochemical Sonogashira-type reaction. In the presence of the catalytic amount of Pd(OAc)(2) and 4-BzO-TEMPO, electro-generated silver acetylides reacted immediately with arylboronic acids to afford the corresponding coupling adducts in high yields. No potential conflict of interest relevant to this article was reported.

MDPI Acta Medica Okayama 1420-3049 16 10 2011 Studies on the Synthesis of DMAP Derivatives by Diastereoselective Ugi Reactions 8815 8832 EN Hiroki Mandai Shunsuke Irie Koichi Mitsudo Seiji Suga Diastereoselective Ugi reactions of DMAP-based aldehydes with α-amino acids and tert-butyl isocyanide were examined. The reactions of 4-(dimethylamino)-2-pyridine-carboxaldehyde with various α-amino acids afforded 2-substituted DMAP derivatives with low diastereoselectivity. On the contrary, reactions with 4-(dimethylamino)-3-pyridine-carboxaldehyde delivered 3-substituted DMAP derivatives with moderate to high diastereoselectivity. The combination of α-amino acid and DMAP-based aldehyde is thus important to achieve high diastereoselectivity. Kinetic resolution of a secondary alcohol using a chiral DMAP derivative obtained through these reactions was also examined. No potential conflict of interest relevant to this article was reported.

Acta Medica Okayama 64 24 2008 RhCl3/amine-catalyzed [2+2+2] cyclization of alkynes 5800 5807 EN Kenta Yoshida Ichiro Morimoto Koichi Mitsudo Hideo Tanaka <p>The RhCl3-3H(2)O/i-Pr2NEt-catalyzed [2+2+2] cyclotrimerization of alkynes has been achieved. The reaction can be widely used for various alkynes and provides tri- OF hexa-substituted benzenes regioselectively in high yields. The [2+2+2] cycloaddition of diynes and alkynes is also developed, and it affords benzene derivatives in moderate to high yields.</p> No potential conflict of interest relevant to this article was reported.

Acta Medica Okayama 49 15 2008 Facile synthetic procedure for and electrochemical properties of hexa(2-thienyl)benzenes directed toward electroactive materials 2363 2365 EN Kenta Yoshida Ichiro Morimoto Koichi Mitsudo Hideo Tanaka <p>In the presence of RhCl3 center dot 3H(2)O and i-Pr2NEt, the cyclotrimerization of di(2-thienyl)acetylenes proceeded smoothly to afford hexa(2-thienyl)benzenes. CV analysis of the hexa(2-thienyl)benzenes showed that they may be useful as electroactive materials.</p> No potential conflict of interest relevant to this article was reported.