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Development of resin-supported alloxazine-type flavin catalysts

Research Project

Project/Area Number 18K05124
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionThe University of Tokushima

Principal Investigator

MINAGAWA Keiji  徳島大学, 教養教育院, 教授 (70250959)

Co-Investigator(Kenkyū-buntansha) 今田 泰嗣  徳島大学, 大学院社会産業理工学研究部(理工学域), 教授 (60183191)
荒川 幸弘  徳島大学, 大学院社会産業理工学研究部(理工学域), 助教 (70709203)
Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2020: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords有機分子触媒 / 酸化触媒 / フラビン触媒 / 高分子担持触媒 / 酸素酸化反応 / フラビニウム塩 / 過酸化水素酸化反応 / 酸化反応 / フラビン / 担持型触媒 / フロー反応系
Outline of Final Research Achievements

We have established a general method for preparing a series of resin-supported alloxazine-type flavin catalysts having substituents on the alloxazine skeleton based on the method for preparing resin-supported isoalloxazine-type flavin catalysts that we have already reported. Catalytic activity of a series of resin-supported alloxazine-type flavin catalysts for oxidation reactions was studied, the correlation between the substituents on the alloxazine skeleton and the catalytic activity was clarified, and it was shown that these resin-supported flavin catalysts can be used as practical catalysts in various green oxygenation reactions. In the process of establishing a synthetic method for resin-supported flavin catalysts, a general synthetic method for a series of 4a-hydroxyisoalloxazines having a substituent on the isoalloxazine skeleton was also established, and it was shown that these 4a-hydroxyisoalloxazines can be used as practical catalysts in various green oxygenation reactions.

Academic Significance and Societal Importance of the Research Achievements

化学工業プロセスにおいて多用される酸素添加反応の理想の形は、金属触媒を必要とせず、酸素あるいは過酸化水素を末端酸化剤とする反応である。これらの条件を満たす有機分子酸化触媒として、均一系フラビニウム塩触媒が我々を中心として開発されてきたが、実用的な触媒としてはその取扱いの容易さと合成の簡便さが求められていた。本研究で開発したレジン担持アロキサジン型フラビン触媒および4a-ヒドロキシイソアロキサジン型フラビン触媒は、高い触媒活性に加えて合成の簡便さと取り扱いの容易さを兼ね備えた実用的な酸素添加触媒であり、学術的および社会的両面で大きな意義がある。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (16 results)

All 2021 2020 2019 2018 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results,  Open Access: 8 results) Presentation (7 results) (of which Int'l Joint Research: 2 results) Remarks (1 results)

  • [Journal Article] Alloxazinium-Resins as Readily Available and Reusable Oxidation Catalysts2021

    • Author(s)
      Yukihiro Arakawa, Takayuki Kawahara, Keiji Minagawa, Yasushi Imada
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 94

    • NAID

      130008066556

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Nucleophilic Addition to Nitrones Using a Flow Microreactor2020

    • Author(s)
      Yukihiro Arakawa, Shun Ueta, Takuma Okamoto, Keiji Minagawa, Yasushi Imada
    • Journal Title

      Synlett

      Volume: 31 Issue: 09 Pages: 866-870

    • DOI

      10.1055/s-0039-1691601

    • NAID

      120006959768

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] An uncommon use of irradiated flavins: Br?nsted acid catalysis2020

    • Author(s)
      Yukihiro Arakawa, Tomohiro Mihara, Hiroki Fujii, Keiji Minagawa, Yasushi Imada
    • Journal Title

      Chemical Communications

      Volume: 56 Issue: 42 Pages: 5661-5664

    • DOI

      10.1039/d0cc01960g

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Preparation of flavin-containing mesoporous network polymers and their catalysis2020

    • Author(s)
      Yukihiro Arakawa、Fumiaki Sato、Kenta Ariki、Keiji Minagawa、Yasushi Imada
    • Journal Title

      Tetrahedron Letters

      Volume: 61 Issue: 14 Pages: 151710-151710

    • DOI

      10.1016/j.tetlet.2020.151710

    • NAID

      120007188797

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Efficient Use of Photons in Photoredox/Enamine Dual Catalysis with a Peptide-Bridged Flavin-Amine Hybrid2019

    • Author(s)
      Takuma Tagami、Yukihiro Arakawa、Keiji Minagawa、Yasushi Imada
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 17 Pages: 6978-6982

    • DOI

      10.1021/acs.orglett.9b02567

    • NAID

      120006877715

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Greener Preparation of 5-Ethyl-4a-hydroxyisoalloxazine and Its Use for Catalytic Aerobic Oxygenations2019

    • Author(s)
      Oonishi Takahiro、Kawahara Takayuki、Arakawa Yukihiro、Minagawa Keiji、Imada Yasushi
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2019 Issue: 8 Pages: 1791-1795

    • DOI

      10.1002/ejoc.201801865

    • NAID

      120006784693

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Advanced Flavin Catalysts Elaborated with Polymers2018

    • Author(s)
      Yukihiro Arakawa, Keiji Minagawa, Yasushi Imada
    • Journal Title

      Polymer Journal

      Volume: 50 Issue: 10 Pages: 941-949

    • DOI

      10.1038/s41428-018-0089-8

    • NAID

      120006576963

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Enzyme-like Regiodivergent Behavior of a Flavopeptide Catalyst in Aerobic Baeyer-Villiger Oxidation2018

    • Author(s)
      Ken Yamanomoto, Hazuki Kita, Yukihiro Arakawa, Keiji Minagawa, Yasushi Imada
    • Journal Title

      CHIMIA

      Volume: 72 Issue: 12 Pages: 866-869

    • DOI

      10.2533/chimia.2018.866

    • NAID

      120006771697

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] 空気酸化―樹脂担持法による新規フラビニウム塩の合成2020

    • Author(s)
      坂東新之助, 荒川幸弘, 南川慶二, 今田泰嗣
    • Organizer
      第35回中国四国地区高分子若手研究会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 1,2-ビス(アルキルアミド)シクロヘキサンのゲル化を利用した含フラビン物理ゲルの物性評価2020

    • Author(s)
      三好正敏, 荒川幸弘, 南川慶二, 今田泰嗣
    • Organizer
      第35回中国四国地区高分子若手研究会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Nucleophilic Addition of Vinyl Ethers to a Flavinium Salt2020

    • Author(s)
      Naoki Hasegawa, Yukihiro Arakawa, Keiji Minagawa, Yasushi Imada
    • Organizer
      The 6th International Forum on Advanced Technologies 2020 (IFAT 2020)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] LDH固定化イソアロキサジン触媒の合成とその触媒作用2019

    • Author(s)
      大内幸一, 荒川幸弘,南川慶二, 今田泰嗣
    • Organizer
      2019年日本化学会中国四国支部大会徳島大会
    • Related Report
      2019 Research-status Report
  • [Presentation] Practical Preparation of N5-Ethylated Flavin Catalysts2018

    • Author(s)
      Takahiro Oonishi, Takayuki Kawahara, Yukihiro Arakawa, Keiji Minagawa, Yasushi Imada
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-14)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] 高分子担持型N5位エチル化フラビンの合成とその触媒作用2018

    • Author(s)
      川﨑康平, 荒川幸弘, 南川慶二, 今田泰嗣
    • Organizer
      2018年日本化学会中国四国支部大会
    • Related Report
      2018 Research-status Report
  • [Presentation] N5-エチル-4a-ヒドロキシイソアロキサジンの実用的合成法とその酸素酸化触媒機能2018

    • Author(s)
      川原孝之, 大西崇裕, 荒川幸弘,南川慶二, 今田泰嗣
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Remarks] 徳島大学大学院社会産業理工学研究部応用化学系物質合成化学A3講座ホームページ

    • URL

      http://www.chem.tokushima-u.ac.jp/A3/research.html

    • Related Report
      2018 Research-status Report

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Published: 2018-04-23   Modified: 2022-01-27  

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