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Development of N(5)-Unsubstituted Neutral Flavin Catalysts with High Catalytic Activity towards Oxidation Reactions

Research Project

Project/Area Number 25620086
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionThe University of Tokushima

Principal Investigator

IMADA Yasushi  徳島大学, ソシオテクノサイエンス研究部, 教授 (60183191)

Co-Investigator(Kenkyū-buntansha) MINAGAWA Keiji  徳島大学, 大学院ソシオテクノサイエンス研究部, 准教授 (70250959)
ARAKAWA Yukihiro  徳島大学, 大学院ソシオテクノサイエンス研究部, 助教 (70709203)
Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2014: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2013: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Keywordsフラビン触媒 / 酸化反応 / 反応場の構築 / 酸素酸化反応 / 担持型触媒 / 反応場 / 酸素添加反応
Outline of Final Research Achievements

We have prepared novel N(5)-unsubstituted neutral flavin catalysts bearing effective reaction site as highly active and practical organocatalysts. These include (1) supramolecular flavin gel catalysts by self-assembly of flavin-containing low-molecular-weight gelators, (2) layered double hydroxide-supported flavin catalysts by intercalation of hydrotalcite by flavin carboxylic acid derivatives, and (3) polymer-supported flavin catalysts by co-polymerization of flavin-containing monomers such as flavin-containing styrene and flavin-containing methacrylate. These novel catalysts did not catalyze oxygenation of sulfides; however, they exihibit high catalytic activity towards aerobic hydrogenation reactions due to the reaction site introduced around the flavin molecules.

Report

(3 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • Research Products

    (22 results)

All 2015 2014 2013

All Journal Article (7 results) (of which Peer Reviewed: 7 results,  Acknowledgement Compliant: 3 results) Presentation (15 results) (of which Invited: 4 results)

  • [Journal Article] Flavin-Functionalized Gold Nanoparticles as an Efficient Catalyst for Aerobic Organic Transformations2015

    • Author(s)
      Yasushi Imada, Motonari Ohsaki, Mikiko Noguchi, Takatoshi Maeda, Misa Fujiki, Soichiro Kawamorita, Naruyoshi Komiya, and Takeshi Naota
    • Journal Title

      Chem. Cat. Chem.

      Volume: 7 Issue: 1 Pages: 99-106

    • DOI

      10.1002/cctc.201402619

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Highly Fluorescent Flavins: A Molecular Design Rationale for Quenching Protection Based on Repulsive and Attractive Control of Molecular Alignment2015

    • Author(s)
      Haruka Suzuki, Ryo Inoue, Soichiro Kawamorita, Naruyoshi Komiya, Yasushi Imada and Takeshi Naota
    • Journal Title

      Chemistry-A European Journal

      Volume: 21

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Ring-expanding metathesis oligomerization of cyclic nitrones2014

    • Author(s)
      Yasushi Imada, Chiaki Okita, Hiroki Maeda, Masayuki Kishimoto, Yoshinori Sugano, Hiroyuki Kaneshiro, Yuri Nishida, Soichiro Kawamorita, Naruyoshi Komiya, and Takeshi Naota
    • Journal Title

      European Journal of Organic Chemistry

      Volume: nothing Issue: 26 Pages: 5670-5674

    • DOI

      10.1002/ejoc.201402859

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Oxidation of Sulfides with Hydrogen Peroxide Catalyzed by Vitamin B2 Derivatives2013

    • Author(s)
      Yasushi Imada, Masamitsu Takagishi, Naruyoshi Komiya, and Takeshi Naota
    • Journal Title

      Synth. Commun

      Volume: 43 Issue: 22 Pages: 3064-3071

    • DOI

      10.1080/00397911.2013.767912

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Aerobic Oxidation of Sulfides with Vitamin B2-derived Organocatalyst2013

    • Author(s)
      Yasushi Imada, Itoko Tonomura, Naruyoshi Komiya and Takeshi Naota
    • Journal Title

      Synlett

      Volume: 24 Issue: 13 Pages: 1679-1682

    • DOI

      10.1055/s-0033-1339276

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Non-Covalently Dendronized Flavins as Organocatalysts for Aerobic Reduction of Olefins2013

    • Author(s)
      Yasushi Imada, Yudai Kugimiya, Shotaro Iwata, Naruyoshi Komiya and Takeshi Naota
    • Journal Title

      Tetrahedron

      Volume: 69 Issue: 40 Pages: 8572-8578

    • DOI

      10.1016/j.tet.2013.07.082

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Oxidation of Sulfides with Hydrogen Peroxide Catalyzed by Vitamin B2 Derivatives2013

    • Author(s)
      Yasushi Imada, Masamitsu Takagishi, Naruyoshi Komiya and Takeshi Naota
    • Journal Title

      Synthetic Communications

      Volume: 43 Issue: 2 Pages: 3064-3071

    • DOI

      10.1016/j.tet.2013.11.024

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] アミノ基含有樹脂へのフラビン分子触媒の担持2015

    • Author(s)
      山野本健, 荒川幸弘, 南川慶二, 今田泰嗣
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学船橋キャンパス(千葉県船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] カチオン性フラビン分子調製法の開発2015

    • Author(s)
      大西崇裕, 幸田貴大, 荒川幸弘, 南川慶二, 今田泰嗣
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学船橋キャンパス(千葉県船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 陽イオン交換樹脂担持型カチオン性フラビン分子の酸化触 媒作用2015

    • Author(s)
      幸田貴大, 大西崇裕, 荒川幸弘, 南川慶二, 今田泰嗣
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学船橋キャンパス(千葉県船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 含フラビンポリスチレンの合成と触媒作用2015

    • Author(s)
      河内梨紗, 荒川幸弘, 南川慶二, 今田泰嗣
    • Organizer
      日本化学会第95 春季年 会
    • Place of Presentation
      日本大学船橋キャンパス(千葉県船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] フラビン分子触媒のレジンへの担持と触媒作用2014

    • Author(s)
      山野本健, 荒川幸弘, 南川慶二, 今田泰嗣
    • Organizer
      2014 年日本化学会中 国四国支部大会
    • Place of Presentation
      山口大学吉田キャンパス(山口県山口市)
    • Year and Date
      2014-11-08 – 2014-11-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] LDH 固定化フラビン触媒の合成とその触媒作用2014

    • Author(s)
      芥川遼, 南川慶二, 荒川幸弘, 今田泰嗣
    • Organizer
      2014 年日本化学会中 国四国支部大会
    • Place of Presentation
      山口大学吉田キャンパス(山口県山口市)
    • Year and Date
      2014-11-08 – 2014-11-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] 陽イオン交換樹脂を利用するカチオン性フラビンの調製と 触媒反応2014

    • Author(s)
      大西崇裕, 幸田貴大, 荒川幸弘, 南川慶二, 今田泰嗣
    • Organizer
      2014 年日本化学会中国四国支部大会
    • Place of Presentation
      山口大学吉田キャンパス(山口県山口市)
    • Year and Date
      2014-11-08 – 2014-11-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] 高分子固定化フラビン触媒の開発2014

    • Author(s)
      荒川幸弘, 大西崇裕, 幸田貴大, 佐藤文彬, 南川慶二, 今田泰嗣
    • Organizer
      第63 回高分 子討論会
    • Place of Presentation
      長崎大学文教キャンパス(長崎県長崎市)
    • Year and Date
      2014-09-24 – 2014-09-26
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] フラビン分子を触媒とするオレフィンの水素化反応2014

    • Author(s)
      今田泰嗣
    • Organizer
      第30 回若手化学者のための化学道場
    • Place of Presentation
      下電ホテル(岡山県倉敷市)
    • Year and Date
      2014-08-29 – 2014-08-30
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] フラビン触媒を用いた酸素酸化システムの開発,2014

    • Author(s)
      今田泰嗣
    • Organizer
      第70 回白鷺セミナー
    • Place of Presentation
      大阪府立大学中百舌鳥キャンパス(大阪府堺市)
    • Year and Date
      2014-07-25
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 多孔性高分子固定化フラビンの合成とこれを触媒とするオレフィンの水素添加反応2014

    • Author(s)
      佐藤 文彬, 荒川 幸弘, 南川 慶二, 今田 泰嗣
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(愛知県名古屋市)
    • Related Report
      2013 Research-status Report
  • [Presentation] Flavin Catalysts Captured in Network Polymers2013

    • Author(s)
      Fumiaki Sato, Yukihiro Arakawa, Keiji Minagawa and Yasushi Imada
    • Organizer
      Advanced Molecular Transformations by Organocatalysts 1st International Conference & 6th Symposium on Organocatalysis
    • Place of Presentation
      Otsu Pronce Hotel (Otsu, Shiga, Japan)
    • Related Report
      2013 Research-status Report
  • [Presentation] フラビン分子を触媒とする酸化反応―酵素に倣い,酵素を超える反応を目指して―2013

    • Author(s)
      今田 泰嗣
    • Organizer
      第33回有機合成若手セミナー
    • Place of Presentation
      神戸大学(兵庫県神戸市)
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 多孔性高分子固定化フラビンの合成とその触媒作用2013

    • Author(s)
      佐藤 文彬, 荒川 幸弘, 南川 慶二, 今田 泰嗣
    • Organizer
      第33回有機合成若手セミナー
    • Place of Presentation
      神戸大学(兵庫県神戸市)
    • Related Report
      2013 Research-status Report
  • [Presentation] グルタミド部位を有するシクロメタル化イリジウム錯体の合成と発光特性2013

    • Author(s)
      大槻 恭平, 川守田 創一郎, 小宮 成義, 今田 泰嗣, 直田 健
    • Organizer
      錯体化学会第63回討論会
    • Place of Presentation
      琉球大学(沖縄県中頭郡西原町)
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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