Details of the Researcher

PHOTO

Jun Kikuchi
Section
Graduate School of Pharmaceutical Sciences
Job title
Assistant Professor
Degree
  • 博士(理学)(東北大学)

  • 修士(理学)(東北大学)

e-Rad No.
20802656

Research History 2

  • 2022/01 - Present
    東北大学 大学院薬学研究科 助教

  • 2017/04 - 2021/12
    Tohoku University Graduate School of Science, Department of Chemistry

Education 2

  • Tohoku University

    2012/04 - 2017/03

  • Tohoku University Faculty of Science

    2008/04 - 2012/03

Research Interests 1

  • 有機合成化学

Research Areas 1

  • Nanotechnology/Materials / Synthetic organic chemistry /

Awards 3

  1. Outstanding Reviewer for Organic Chemistry Frontiers in 2023

    2024/03 Organic Chemistry Frontiers, The Royal Society of Chemistry

  2. Outstanding Reviewer for Organic Chemistry Frontiers in 2022

    2023/03 Organic Chemistry Frontiers, The Royal Society of Chemistry

  3. 化学専攻賞

    2017/03 東北大学

Papers 31

  1. Iodine(III)-Mediated Cyclization Cascade of Diynes to Benzofulvene Derivatives Peer-reviewed

    Jun Kikuchi, Roi Nakajima, Eunsang Kwon, Naohiko Yoshikai

    Organic Letters 2025/08

    DOI: 10.1021/acs.orglett.5c03133  

  2. 2-(Cyanomethyl)benzimidazole Derivatives as 1,3-Dicarbonyl Analogues for a Kinetically Controlled Diastereo- and Enantioselective Mannich-Type Reaction Catalyzed by Chiral Phosphoric Acid Peer-reviewed

    Organic Letters 2025/05

    DOI: 10.1021/acs.orglett.5c01478  

  3. Stable and responsive atropisomerism around a carbon–iodine bond Peer-reviewed

    Shohei Abe, Jun Kikuchi, Arimasa Matsumoto, Naohiko Yoshikai

    Chem 2025/04

    DOI: 10.1016/j.chempr.2025.102527  

    ISSN: 2451-9294

  4. Development of a flow photochemical process for a π-Lewis acidic metal-catalyzed cyclization/radical addition sequence: in situ-generated 2-benzopyrylium as photoredox catalyst and reactive intermediate Peer-reviewed

    Masahiro Terada, Zen Iwasaki, Ryohei Yazaki, Shigenobu Umemiya, Jun Kikuchi

    Beilstein Journal of Organic Chemistry 2024/08

    DOI: 10.3762/bjoc.20.173  

  5. Three-component N-alkenylation of azoles with alkynes and iodine(III) electrophile: synthesis of multisubstituted N-vinylazoles Peer-reviewed

    Jun Kikuchi, Roi Nakajima, Naohiko Yoshikai

    Beilstein Journal of Organic Chemistry 2024/04

    DOI: 10.3762/bjoc.20.79  

  6. Three-Component Friedel–Crafts-Type Difunctionalization of Ynamides with (Hetero)arenes and Iodine(III) Electrophile Peer-reviewed

    Jun kikuchi, Toya Nagata, Shingo Ito, Naohiko Yoshikai

    Organic Chemistry Frontiers 2024/04

    DOI: 10.1039/D4QO00489B  

  7. Consecutive π-Lewis Acidic Metal-Catalysed Cyclisation/Photochemical Radical Addition Promoted by in situ Generated 2-Benzopyrylium as the Photoredox Catalyst Peer-reviewed

    Masahiro Terada, Ryohei Yazaki, Ren Obayashi, Zen Iwasaki, Umemiya Shigenobu, Jun Kikuchi

    Chemical Science 2024/03

    DOI: 10.1039/d4sc00808a  

    ISSN: 2041-6520 2041-6539

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    <jats:p>A π-Lewis acidic metal-catalysed cyclisation/photochemical radical addition sequence was developed, which utilises <jats:italic>in situ</jats:italic> generated 2-benzopyrylium cation intermediates as the photoredox catalyst and electrophilic substrates to form 1<jats:italic>H</jats:italic>-isochromene derivatives in...</jats:p>

  8. Stereoselective Approach to Multisubstituted Enolates from Unactivated Alkynes: Oxyalkylidenation of Alkynyl Ketone Enolates with Aldehydes Peer-reviewed

    Shuma Sasaki, Jun Kikuchi, Shingo Ito, Naohiko Yoshikai

    The Journal of Organic Chemistry 2023/09/21

    DOI: 10.1021/acs.joc.3c01615  

  9. Site-Selective C–H Alkenylation of N-Heteroarenes by Ligand-Directed Co/Al and Co/Mg Cooperative Catalysis Peer-reviewed

    Yuri Saito, Jun Kikuchi, Chen Wang, Naohiko Yoshikai

    Angew. Chem. Int. Ed. 2023/03

    DOI: 10.1002/anie.202301006  

  10. Stereoselective Synthesis of β-Alkoxy-β-amido Vinylbenziodoxoles via Iodo(III)etherification of Ynamides Peer-reviewed

    Jun Kikuchi, Kaito Maesaki, Shuma Sasaki, Weifan Wang, Shingo Ito, Naohiko Yoshikai

    Organic Letters 2022/09

    DOI: 10.1021/acs.orglett.2c02570  

  11. Kinetic Resolution of Racemic Tertiary Allylic Alcohols through SN2’ Reaction Using a Chiral Bisphosphoric Acid/Silver(I) Salt Co-catalyst System Peer-reviewed

    Satavisha Kayal, Jun Kikuchi, Naoya Shinagawa, Umemiya Shigenobu, Masahiro Terada

    Chemical Science 2022/07

    Publisher: Royal Society of Chemistry (RSC)

    DOI: 10.1039/d2sc03052g  

    ISSN: 2041-6520

    eISSN: 2041-6539

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    A highly efficient kinetic resolution (KR) of racemic tertiary allylic alcohols was achieved through an intramolecular allylic substitution reaction using a co-catalyst system composed of chiral bisphosphoric acid and silver...

  12. Development of chiral bisphosphoric acid/Boronic acid Co-catalyst system for enantioselective SN2’ reaction Peer-reviewed

    Satavisha Kayal, Jun Kikuchi, Naoya Shinagawa, Shigenobu Umemiya, Masahiro Terada

    Tetrahedron 132412-132412 2021/09

    Publisher: Elsevier BV

    DOI: 10.1016/j.tet.2021.132412  

    ISSN: 0040-4020

  13. Dynamic Parallel Kinetic Resolution of α-Ferrocenyl Cation Initiated by Chiral Brønsted Acid Catalyst Peer-reviewed

    Yasunori Toda, Toshinobu Korenaga, Ren Obayashi, Jun Kikuchi, Masahiro Terada

    Chemical Science 2021/06

  14. Radical Addition Reaction between Chromenols and Toluene Derivatives Initiated by Brønsted Acid Catalyst under Light Irradiation Peer-reviewed

    Jun Kikuchi, Shota Kodama, Masahiro Terada

    Organic Chemistry Frontiers 2021/05

    DOI: 10.1039/D1QO00657F.  

  15. Chiral Phosphoric Acid Catalyzed Enantioselective [4 + 2] Cycloaddition Reaction of α-Fluorostyrenes with Imines Peer-reviewed

    Jun Kikuchi, Haiting Ye, Masahiro Terada

    Organic Letters 22 (22) 8957-8961 2020/11/02

    Publisher: American Chemical Society (ACS)

    DOI: 10.1021/acs.orglett.0c03360  

    ISSN: 1523-7060

    eISSN: 1523-7052

  16. Chiral Phosphoric Acid-Catalyzed Enantioselective Phospha-Michael-Type Addition Reaction of Diarylphosphine Oxides with Alkenyl Benzimidazoles Peer-reviewed

    Linan Hou, Jun Kikuchi, Haiting Ye, Ming Bao, Masahiro Terada

    The Journal of Organic Chemistry 85 (22) 14802-14809 2020/09/29

    Publisher: American Chemical Society (ACS)

    DOI: 10.1021/acs.joc.0c01840  

    ISSN: 0022-3263

    eISSN: 1520-6904

  17. One‐Pot Synthesis of Enantioenriched β‐Amino Secondary Amides via Enantioselective [4+2] Cycloaddition Reaction of Vinyl Azides with N‐Acyl Imines Catalyzed by Chiral Brønsted Acid Peer-reviewed

    Taishi Nakanishi, Jun Kikuchi, Atsushi Kaga, Shunsuke Chiba, Masahiro Terada

    Chemistry – A European Journal 2020/05

    DOI: 10.1002/chem.202002049  

    ISSN: 1521-3765

  18. Chiral Brønsted Acid-Catalyzed Enantioconvergent Propargylic Substitution Reaction of Racemic Secondary Propargylic Alcohols with Thiols Peer-reviewed

    Jun Kikuchi, Kyohei Takano, Yusuke Ota, Shigenobu Umemiya, Masahiro Terada

    Chemistry - A European Journal 2020/04/09

    DOI: 10.1002/chem.202001609  

    ISSN: 0947-6539

  19. Chiral Strong Brønsted Acid-Catalyzed Enantioselective Addition Reaction of Simple Olefins with Ethyl Glyoxylate Peer-reviewed

    Jun Kikuchi, Yuki Aizawa, Masahiro Terada

    Organic Chemistry Frontiers 2020/04

    DOI: 10.1039/d0qo00448k  

    ISSN: 2052-4129

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    <p>An enantioselective intermolecular carbonyl-ene reaction and a Friedel-Crafts-type reaction of 1,1,2-trisubstituted and 1,2-disubstituted simple olefins with ethyl glyoxylate were developed using F10BINOL-derived N-sulfonyl phosphoramide as the chiral strong Brønsted acid...</p>

  20. Non‐enzymatic Hybrid Catalysis for Stereoconversion of l‐Amino Acid Derivatives to d‐Isomers Peer-reviewed

    Yuya Nagato, Mari Kiyokawa, Yusuke Ueki, Jun Kikuchi, Kohsuke Ohmatsu, Masahiro Terada, Takashi Ooi

    Asian Journal of Organic Chemistry 2020/02

    Publisher: Wiley

    DOI: 10.1002/ajoc.202000067  

    ISSN: 2193-5807

  21. Mechanism and Origin of Stereoselectivity in Chiral Phosphoric Acid-Catalysed Aldol-Type Reactions of Azlactones with Vinyl Ethers Peer-reviewed

    Kyohei Kanomata, Yuki Nagasawa, Yukihiro Shibata, Masahiro Yamanaka, Fuyuki Egawa, Jun Kikuchi, Masahiro Terada

    Chemistry - A European Journal 26 (15) 3364-3372 2020

    DOI: 10.1002/chem.201905296  

    ISSN: 0947-6539

    eISSN: 1521-3765

  22. Chiral Brønsted Acid-Catalyzed Formal α-Vinylation of Cyclopentanones for the Enantioselective Construction of Quaternary Carbon Centers Peer-reviewed

    Satavisha Kayal, Jun Kikuchi, Masahiro Shimizu, Masahiro Terada

    ACS Catalysis 9 (8) 6846-6850 2019

    DOI: 10.1021/acscatal.9b01780  

    eISSN: 2155-5435

  23. Enantioselective Addition Reaction of Azlactones with Styrene Derivatives Catalyzed by Strong Chiral Brønsted Acid Peer-reviewed

    Jun Kikuchi, Masahiro Terada

    Angewandte Chemie International Edition 58 (25) 8458-8462 2019

    DOI: 10.1002/anie.201903111  

    ISSN: 1433-7851

    eISSN: 1521-3773

  24. Bis-phosphoric Acid Derived from BINOL Dimer as a Chiral Brønsted Acid Catalyst for Enantioselective Transformations Peer-reviewed

    Masahiro Terada, Yogesh Gupta, Jun Kikuchi

    Chemistry Letters 48 (3) 260-263 2019

    DOI: 10.1246/cl.180977  

    ISSN: 0366-7022

    eISSN: 1348-0715

  25. F10BINOL-derived Chiral Phosphoric Acid-Catalyzed Enantioselective Carbonyl-Ene Reaction: Theoretical Elucidation of Stereochemical Outcomes Peer-reviewed

    Jun Kikuchi, Hiromu Aramaki, Hiroshi Okamoto, Masahiro Terada

    Chemical Science 10 (5) 1426-1433 2019

    DOI: 10.1039/C8SC03587C  

    ISSN: 2041-6520

    eISSN: 2041-6539

  26. Chiral Brønsted Acid-Catalyzed Intramolecular SN2' Reaction for Enantioselective Construction of Quaternary Stereogenic Center Peer-reviewed

    Masahiro Shimizu, Jun Kikuchi, Azusa kondoh, Masahiro Terada

    Chemical Science 9 (26) 5747-5757 2018

    DOI: 10.1039/c8sc01942h  

    ISSN: 2041-6520

    eISSN: 2041-6539

  27. Chiral Phosphoric Acid-Catalyzed Enantioselective Ring Expansion Reaction of 1,3-Dithiane Derivatives: Case Study of the Nature of Ion-Pairing Interaction Peer-reviewed

    Feng Li, Toshinobu Korenaga, Taishi Nakanishi, Jun Kikuchi, Masahiro Terada

    J. Am. Chem. Soc 140 (7) 2629-2642 2018

    Publisher: American Chemical Society (ACS)

    DOI: 10.1021/jacs.7b13274  

    ISSN: 0002-7863

    eISSN: 1520-5126

  28. A FISCHER INDOLIZATION STRATEGY TOWARD THE TOTAL SYNTHESIS OF (-)-GONIOMITINE Peer-reviewed

    Beau P. Pritchett, Jun Kikuchi, Yoshitaka Numajiri, Brian M. Stoltz

    HETEROCYCLES 95 (2) 1245-1253 2017/01

    DOI: 10.3987/COM-16-S(S)80  

    ISSN: 0385-5414

    eISSN: 1881-0942

  29. Enantioselective Pd-Catalyzed Allylic Alkylation Reactions of Dihydropyrido[1,2-a]indolone Substrates: Efficient Syntheses of (-)-Goniomitine, (+)-Aspidospermidine, and (-)-Quebrachamine Peer-reviewed

    Beau P. Pritchett, Jun Kikuchi, Yoshitaka Numajiri, Brian M. Stoltz

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 55 (43) 13529-13532 2016/10

    DOI: 10.1002/anie.201608138  

    ISSN: 1433-7851

    eISSN: 1521-3773

  30. Chiral Phosphoric Acid Catalyzed Diastereo- and Enantioselective Mannich-Type Reaction between Enamides and Thiazolones Peer-reviewed

    Jun Kikuchi, Norie Momiyama, Masahiro Terada

    ORGANIC LETTERS 18 (11) 2521-2523 2016/06

    DOI: 10.1021/acs.orglett.6b00857  

    ISSN: 1523-7060

    eISSN: 1523-7052

  31. Perfluorinated Aryls in the Design of Chiral Bronsted Acid Catalysts: Catalysis of Enantioselective [4+2] Cycloadditions and Ene Reactions of Imines with Alkenes by Chiral Mono-Phosphoric Acids with Perfluoroaryls Peer-reviewed

    Norie Momiyama, Hiroshi Okamoto, Jun Kikuchi, Toshinobu Korenaga, Masahiro Terada

    ACS CATALYSIS 6 (2) 1198-1204 2016/02

    DOI: 10.1021/acscatal.5b02136  

    ISSN: 2155-5435

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Misc. 3

  1. Cobalt selectively annulates Peer-reviewed

    Jun Kikuchi, Naohiko Yoshikai

    Nature Synthesis 2022/08/08

    Publisher: Springer Science and Business Media {LLC}

    DOI: 10.1038/s44160-022-00126-0  

    ISSN: 2731-0582

  2. Enantioconvergent Substitution Reactions of Racemic Electrophiles by Organocatalysis Peer-reviewed

    Jun Kikuchi, Masahiro Terada

    Chemistry – A European Journal 2021/03

    DOI: 10.1002/chem.202100439  

    ISSN: 0947-6539

    eISSN: 1521-3765

  3. Palladium─Catalyzed Acid Chloride Synthesis Peer-reviewed

    KIKUCHI Jun

    76 (7) 730-731 2018/07

Books and Other Publications 5

  1. 遷移金属フリーC−Nクロスカップリング(注目の論文)

    菊池隼

    月刊化学 2024/08

  2. Fe と Ti の協働による芳香族化合物の位置選択的オルト二官能基化(有機金属ハイライト)

    2024/03

  3. 触媒年鑑 「触媒技術の動向と展望 2019」

    近藤梓, 菊池隼, 寺田眞浩

    触媒学会 2019/04

  4. 不斉有機分子触媒としてのアルデヒド

    菊池隼, 寺田眞浩

    月刊化学 2019/01

  5. Development of Organocatalysts and Their Application to Industry

    2018/03

Research Projects 4

  1. 一般財団法人 イオン工学振興財団 研究助成

    2025/08 - 2027/03

  2. 炭素-ハロゲン結合間に軸不斉を持つキラル超原子価ハロゲン化合物の創出と機能開拓

    菊池 隼

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 若手研究

    Institution: 東北大学

    2024/04/01 - 2026/03/31

  3. 2025年度 豊田理研スカラー研究助成

    2025/04 - 2026/03

  4. 共役塩基の一電子酸化に基づく、酸・ラジカル自己リレー型触媒反応系の開発

    菊池 隼

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 若手研究

    Institution: 東北大学

    2019/04 - 2023/03

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    ブレンステッド酸触媒は、古典的かつ汎用性の高い触媒であるが、その触媒作用に基づく反応は依然としてイオン反応の枠組みから脱していない。本研究では、ブレンステッド酸触媒による反応形式の拡充を目的とし、基質のプロトン化により生じたカチオン中間体を光励起することによって強力な一電子酸化剤として機能させ、ラジカル反応へと展開することを試みている。本年度は、前年度までに見出したベンゾピリリウムカチオン中間体の可視光励起を利用したトルエン誘導体とのラジカル反応について、学術論文として報告をした。 また、イミニウムやチオベンゾピリリウムカチオンに代表される他のカチオン中間体の光励起に基づくラジカル付加反応において、キラルブレンステッド酸触媒を作用させることで中程度のエナンチオ選択性の発現が観測されており、不斉ラジカル付加反応へと展開可能であることが確認されている。現在立体選択性の向上に向けて反応条件の検討を行っている。 また、励起カチオン中間体の発生に基づく本反応形式は、ブレンステッド酸触媒だけでなく、ケイ素ルイス酸触媒やπ酸性金属触媒などに代表される他の酸触媒を利用した、より多様な反応系へと展開可能であることがわかった。その一例として、分子内にアルキン部位を有するカルボニル化合物に対して銀触媒を作用させることで、分子内環化反応を起点とした励起カチオン中間体の発生、続くラジカル付加反応の進行が可能であることを見出した。