Faculty Profiles - SATO Eisuke

Papers - SATO Eisuke

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Electrochemical Oxidation of Benzyl Alcohols via Hydrogen Atom Transfer Mediated by 2,2,2-Trifluoroethanol

Takahiro Kawajiri, Masahiro Hosoya, Satoshi Goda, Eisuke Sato, Seiji Suga

Organic Letters 2025.4

Electrogenerated Lewis Acid-Catalyzed Claisen Rearrangement of Allyl Aryl Ethers Reviewed

Yuta Niki, Koichi Mitsudo, Eisuke Sato, Seiji Suga

Organic Letters 2024.12

SNAr Hexafluoroisopropoxylation of Electron-rich Aryl Fluoride with a Catalytic Electrical Input Reviewed

Eisuke Sato, Tomohiro Nakahama, Koichi Mitsudo, Seiji Suga

Chemistry Letters 2024.10

Authorship：Lead author,　Corresponding author Publishing type：Research paper (scientific journal) Publisher：Oxford University Press (OUP)

Abstract

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.

DOI： 10.1093/chemle/upae196

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Electrocatalytic Hydrogenation of Pyridines and Other Nitrogen-Containing Aromatic Compounds Reviewed

Naoki Shida, Yugo Shimizu, Akizumi Yonezawa, Juri Harada, Yuka Furutani, Yusuke Muto, Ryo Kurihara, Junko N. Kondo, Eisuke Sato, Koichi Mitsudo, Seiji Suga, Shoji Iguchi, Kazuhide Kamiya, Mahito Atobe

Journal of the American Chemical Society 2024.10

Electrochemical Synthesis of Heterocyclic Compounds via Carbon–Heteroatom Bond Formation: Direct and Indirect Electrolysis Reviewed

Yasuyuki Okumura, Eisuke Sato, Koichi Mitsudo, Seiji Suga

Chemistry Letters 2024.7

Publishing type：Research paper (scientific journal) Publisher：Oxford University Press (OUP)

Abstract

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.

DOI： 10.1093/chemle/upae146

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Electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines under mild conditions with a proton-exchange membrane reactor Reviewed

Koichi Mitsudo, Atsushi Osaki, Haruka Inoue, Eisuke Sato, Naoki Shida, Mahito Atobe, Seiji Suga

Beilstein Journal of Organic Chemistry 2024.7

Sequential Paired Electrochemical Transformation of Styrene Oxide via Anodic Meinwald Rearrangement and Cathodic Nitromethylation in an Electrochemical Flow Reactor with Catalytic Electrical Input Reviewed

Eisuke Sato, Seiji Suga, Kanon Nagamine, Chika Sasaki, Shumpei Kunimoto, Koichi Mitsudo

Synthesis 2024.5

Electrochemical Coupling Reactions Using Non‐Transition Metal Mediators: Recent Advances Reviewed

Koichi Mitsudo, Yasuyuki Okumura, Eisuke Sato, Seiji Suga

European Journal of Organic Chemistry 2023.12

Alkynylation of Aldehydes Initiated by Cathodic Reduction Reviewed

Eisuke Sato, Mayu Fujii, Koichi Mitsudo, Seiji Suga

ChemElectroChem 2023.12

Anodic Dehydrogenative Aromatization of Tetrahydrocarbazoles Leading to Carbazoles Reviewed

Eisuke Sato, Ayaka Yukiue, Koichi Mitsudo, Seiji Suga

Organic Letters 2023.7

Electrochemical Synthesis of Sultone Derivatives via Dehydrogenative C–O Bond Formation Reviewed International journal

Koichi Mitsudo, Yasuyuki Okumura, Kotaro Yohena, Yuji Kurimoto, Eisuke Sato, Seiji Suga

Organic Letters 25 ( 19 ) 3476 - 3481 2023.5

Language：English Publishing type：Research paper (scientific journal)

Electrochemical dehydrogenative C-O bond formation for the synthesis of sultones was achieved. In the presence of K2CO3 and H2O, constant current electrolysis of [1,1'-biphenyl]-2-sulfonyl chloride afforded an aryl-fused sultone quantitatively. Under the optimized conditions, a variety of sultone derivatives were obtained. Control experiments suggest that the electrochemical oxidation of the sulfonates generated in situ would afford sulfo radical intermediates.

DOI： 10.1021/acs.orglett.3c01062

PubMed

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Electrochemical Cross-Coupling Reactions between Arylboronic Esters and Aryllithiums Using NaBr as a Halogen Mediator Reviewed

Koichi Mitsudo, Keisuke Shigemori, Taro Shibata, Hiroki Mandai, Eisuke Sato, Seiji Suga

Synthesis 2023.2

Language：English Publishing type：Research paper (scientific journal) Publisher：Georg Thieme Verlag {KG}

<jats:p>An electrochemical cross-coupling reaction between arylboronic esters and aryllithiums was developed. The presence of Br− in the electrolyte was found to be essential for the reaction. NaBr was chosen as the electrolyte for its inexpensiveness and abundance, and also acted as a halogen mediator. The reaction proceeded under mild conditions to afford biaryls.</jats:p>

DOI： 10.1055/a-2034-9821

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Electrochemical Carbon-Ferrier Rearrangement Using a Microflow Reactor and Machine Learning-Assisted Exploration of Suitable Conditions Reviewed

Eisuke Sato, Gaku Tachiwaki, Mayu Fujii, Koichi Mitsudo, Takashi Washio, Shinobu Takizawa, Seiji Suga

Organic Process Research & Development 2023.1

Electrochemical Synthesis of Dibenzothiophene S,S-Dioxides from Biaryl Sulfonyl Hydrazides Reviewed

Yasuyuki OKUMURA, Eisuke SATO, Koichi MITSUDO, Seiji SUGA

Electrochemistry 2023

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

Naoki SHIDA, Eisuke SATO

Electrochemistry 2023

Cathodic N–O Bond Cleavage of N-Alkoxy Amide Reviewed

Eisuke SATO, Sayaka OGITA, Koichi MITSUDO, Seiji SUGA

Electrochemistry 2023

Electrochemical Synthesis of Dibenzothiophenes via Intramolecular C–S Cyclization with a Halogen Mediator Reviewed

Koichi Mitsudo, Yuri Tachibana, Eisuke Sato, Seiji Suga

Organic Letters 24 ( 46 ) 8547 - 8552 2022.11

A Facile Access to Spirooxindoles by Halogen-Mediated Electrochemical Semi-pinacol Rearrangement Reviewed

Eisuke SATO, Sae KANGAWA, Koichi MITSUDO, Seiji SUGA

Chemistry Letters 51 ( 11 ) 1067 - 1069 2022.9

Electrochemical hydrogenation of enones using a proton-exchange membrane reactor: selectivity and utility Reviewed

Koichi Mitsudo, Haruka Inoue, Yuta Niki, Eisuke Sato, Seiji Suga

Beilstein Journal of Organic Chemistry 18 1055 - 1061 2022.8

Language：English Publishing type：Research paper (scientific journal) Publisher：Beilstein Institut

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).

DOI： 10.3762/bjoc.18.107

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Other Link： https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-18-107.pdf

Electro-oxidative Trimerization of 1,2-Dimethoxybenzene: Reductive Workup Strategy and Alternating Current Electrolysis to Peel off the Precipitated Radical Cation Ion Pair Reviewed

Eisuke Sato, Yuta Niki, Koichi Mitsudo, Seiji Suga

Chemistry Letters 51 ( 6 ) 629 - 632 2022.6

Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis Reviewed

Eisuke Sato, Mayu Fujii, Hiroki Tanaka, Koichi Mitsudo, Masaru Kondo, Shinobu Takizawa, Hiroaki Sasai, Takeshi Washio, Kazunori Ishikawa, Seiji Suga

The Journal of Organic Chemistry 86 ( 22 ) 16035 - 16044 2021.11

Language：English Publishing type：Research paper (scientific journal) Publisher：American Chemical Society (ACS)

Cyanosilylation of carbonyl compounds provides protected cyanohydrins, which can be converted into many kinds of compounds such as amino alcohols, amides, esters, and carboxylic acids. In particular, the use of trimethylsilyl cyanide as the sole carbon source can avoid the need for more toxic inorganic cyanides. In this paper, we describe an electrochemically initiated cyanosilylation of carbonyl compounds and its application to a microflow reactor. Furthermore, to identify suitable reaction conditions, which reflect considerations beyond simply a high yield, we demonstrate machine learning-assisted optimization. Machine learning can be used to adjust the current and flow rate at the same time and identify the conditions needed to achieve the best productivity.

DOI： 10.1021/acs.joc.1c01242

Web of Science

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Synthesis of Morphinans through Anodic Aryl‐Aryl Coupling Reviewed

Nina Vierengel, Leander Geske, Eisuke Sato, Till Opatz

The Chemical Record 21 ( 9 ) 2344 - 2353 2021.9

Cu-Catalyzed Dehydrogenative C–O Cyclization for the Synthesis of Furan-Fused Thienoacenes Reviewed

Koichi Mitsudo, Yoshiaki Kobashi, Kaito Nakata, Yuji Kurimoto, Eisuke Sato, Hiroki Mandai, Seiji Suga

Organic Letters 23 ( 11 ) 4322 - 4326 2021.6

Electrosynthesis of Phosphacycles via Dehydrogenative C–P Bond Formation Using DABCO as a Mediator Reviewed

Yuji Kurimoto, Jun Yamashita, Koichi Mitsudo, Eisuke Sato, Seiji Suga

Organic Letters 23 ( 8 ) 3120 - 3124 2021.4

Anodic Oxidation as an Enabling Tool for the Synthesis of Natural Products Reviewed

Till Opatz, Leander Geske, Eisuke Sato

Synthesis 52 ( 19 ) 2781 - 2794 2020.10

Language：English Publishing type：Research paper (scientific journal) Publisher：Georg Thieme Verlag KG

Electrochemistry provides a valuable toolbox for organic synthesis and offers an appealing, environmentally benign alternative to the use of stoichiometric quantities of chemical oxidants or reductants. Its potential to control current efficiency along with providing alternative reaction conditions in a classical sense makes electrochemistry a suitable method for large-scale industrial transformations as well as for laboratory applications in the synthesis of complex molecular architectures. Even though research in this field has intensified over the recent decades, many synthetic chemists still hesitate to add electroorganic reactions to their standard repertoire, and hence, the full potential of preparative organic electrochemistry has not yet been unleashed. This short review highlights the versatility of anodic transformations by summarizing their application in natural product synthesis.

1 Introduction

2 Shono-Type Oxidation

3 C–N/N–N Bond Formation

4 Aryl–Alkene/Aryl–Aryl Coupling

5 Cycloadditions Triggered by Oxidation of Electron-Rich Arenes

6 Spirocycles

7 Miscellaneous Transformations

8 Future Prospects

DOI： 10.1055/s-0040-1707154

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Design, synthesis and anti-malarial activities of synthetic analogs of biselyngbyolide B, a Ca2+ pump inhibitor from marine cyanobacteria Reviewed

Eisuke Sato, Maho Morita, Haruo Ogawa, Masato Iwatsuki, Rei Hokari, Aki Ishiyama, Satoshi Ōmura, Arihiro Iwasaki, Kiyotake Suenaga

Bioorganic & Medicinal Chemistry Letters 28 ( 3 ) 298 - 301 2018.2

Language：English Publishing type：Research paper (scientific journal) Publisher：Elsevier BV

Biselyngbyaside, an 18-membered macrolide glycoside from marine cyanobacteria, and its derivatives are known to be sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) inhibitors. Recently, a SERCA orthologue of the malaria parasite, PfATP6, has attracted attention as a malarial drug target. To provide a novel drug lead, we designed new synthetic analogs of biselyngbyolide B, the aglycone of biselyngbyaside, based on the co-crystal structure of SERCA with biselyngbyolide B, and synthesized them using the established synthetic route for biselyngbyolide B. Their biological activities against malarial parasites were evaluated. (C) 2017 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmcl.2017.12.050

Web of Science

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Total Synthesis of Biselyngbyaside Reviewed

Eisuke Sato, Miho Sato, Yurika Tanabe, Naoya Nakajima, Akifumi Ohkubo, Kiyotake Suenaga

The Journal of Organic Chemistry 82 ( 13 ) 6770 - 6777 2017.7