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Aerobic Oxidation Reactions Catalyzed by Flavin Molecules

Research Project

Project/Area Number 18550092
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionOsaka University

Principal Investigator

IMADA Yasushi  Osaka University, Graduate School of Engineering Science, Associate Professor (60183191)

Project Period (FY) 2006 – 2007
Project Status Completed (Fiscal Year 2007)
Budget Amount *help
¥4,130,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥330,000)
Fiscal Year 2007: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2006: ¥2,700,000 (Direct Cost: ¥2,700,000)
Keywordsorganocatalysts / flavin catalysts / aerobic oxidations / environmentally friendry / hydrogenation / diimide / dendrimers / gold nanoparticles / フラビンン触媒 / フラビン触媒 / ヒドラジン / グリーンケミストリー
Research Abstract

Organocatalytic aerobic oxidation is one of the most attractive methods because of availability and safety of molecular oxygen and organocatalysts. In this project, the author developed highly selective and environmentally friendly methods for oxidation of heteroatom compounds as well as hydrogenation of olefins based on the flavin-promoted activation of molecular oxygen.
1. Hydrazine was oxidized readily by flavinium cation-ratalyzed aerobic oxidation to give diazene, which is a highly active hydrogen donor towards unsaturated bonds. Using the system, the author developed environmentally f iendly hydrogenation method for olefins without using metal catalysts and hydrogen gas.
3. Dendrimers bearing diaminopyridine core bind flavin molecules through three-point hydrogen bonding interaction to form flavin-dendrimer complexes. The compexes exhibited high catalytic performance due to the hydrohobic environment around the catalyst.
3. Dendrimers bearing diaminopyridine core bind flavin molecules through three-point hydrogen bonding interaction to fomi flavin-dendrimer complexes. The compexes exhibited high catalytic performance due to the hydrohobic environment around the catalyst.
4. Gold nanoparticles can be functionalized by flavin molecules. The flavin-functionalized gold nanoparticles can be used as catalysts for aerobic oxidation of sulfides and aerobic hydrogenation of of efins.

Report

(3 results)
  • 2007 Annual Research Report   Final Research Report Summary
  • 2006 Annual Research Report
  • Research Products

    (49 results)

All 2008 2007 2006

All Journal Article (12 results) (of which Peer Reviewed: 6 results) Presentation (32 results) Book (2 results) Patent(Industrial Property Rights) (3 results) (of which Overseas: 1 results)

  • [Journal Article] Synthesis and Electrochemical behavior of clothespin-shaped bisflavin compounds2008

    • Author(s)
      Yasushi Imada
    • Journal Title

      Tetrahedron Letters 49

      Pages: 2523-2526

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Synthesis and Electrochemical behavior of clothespin-shaped bisflavin compounds2008

    • Author(s)
      Yasushi, Imada
    • Journal Title

      Tetrahedron Lett 49

      Pages: 2523-2526

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Synthesis and Electrochemical behavior of clothespin-shaped bisflavin compounds2008

    • Author(s)
      Yasushi Imada
    • Journal Title

      Tetrahedron Letters 49(印刷中)

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Oxidation of sulfides with hydrogen peroxide catalyzed by 10,10'-linked bisflavinium perchlorates2007

    • Author(s)
      Yasushi Imada
    • Journal Title

      Tetrahedron Letters 48

      Pages: 937-939

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Flavins as Organocatalysts for Environmentally Benign Molecular Transformations2007

    • Author(s)
      Yasushi Imada
    • Journal Title

      The Chemical Record 7

      Pages: 354-361

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Oxidation of sulfides with hydrogen peroxide catalyzed by 10,10'-linked bisflavinium perchlorates2007

    • Author(s)
      Yasushi, Imada
    • Journal Title

      Tetrahedron Lett 48

      Pages: 937-939

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Flavins as Organocatalysts for Environmentally Benign Molecular Transformations2007

    • Author(s)
      Yasushi, Imada
    • Journal Title

      Chem. Rec 7

      Pages: 354-361

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Flavins as organocatalysts for environmentally benign molecular transformations2007

    • Author(s)
      Yasushi Imada
    • Journal Title

      The Chemical Record 7・6

      Pages: 354-361

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Oxidation of sulfides with hydrogen peroxide catalyzed by 10,10'-linked bisflavinium perchlorates2007

    • Author(s)
      Yasushi Imada
    • Journal Title

      Tetrahedron Letters 48・6

      Pages: 937-939

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Flavin-Catalyzed Oxidation of Amines and Sulfides with Molecular Oxygen: Biomimetic Green Oxidation2006

    • Author(s)
      Yasushi Imada
    • Journal Title

      Chemistry, Asian Journal 1

      Pages: 136-147

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Flavin-Catalyzed Oxidation of Amines and Sulfides with Molecular Oxygen : Biomimetic Green Oxidation2006

    • Author(s)
      Yasushi, Imada
    • Journal Title

      Chem. Asian J 1

      Pages: 136-147

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Flavin-Catalyzed Oxidation of Amines and Sulfides with Molecular Oxygen : Biomimetic Green Oxidation2006

    • Author(s)
      Yasushi Imada
    • Journal Title

      Chemistry an Asian Journal 1・1-2

      Pages: 136-147

    • Related Report
      2006 Annual Research Report
  • [Presentation] 環状ニトロンの環拡大メタセシス反応を利用した大環状ポリアミンの合成2008

    • Author(s)
      沖田千明
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      東京(立教大学池袋キャンパス)
    • Year and Date
      2008-03-30
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis of macrocyclic polyamines by ring expanding methathesis oligomerization of cyclic nitrones2008

    • Author(s)
      Chiaki, Okita
    • Organizer
      The 88th Spring Meeting of The Chemical Society of Japan
    • Place of Presentation
      Tokyo
    • Year and Date
      2008-03-30
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] 環状ニトロンの環拡大メタセシス反応を利用した大環状ポリアミンの合成2008

    • Author(s)
      今田泰嗣
    • Organizer
      日本化学会第88春年会
    • Place of Presentation
      立教大学(東京都)
    • Year and Date
      2008-03-30
    • Related Report
      2007 Annual Research Report
  • [Presentation] フラビン修飾金ナノ粒子の合成とジイミド還元における触媒能2008

    • Author(s)
      野口三紀子
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      東京(立教大学池袋キャンパス)
    • Year and Date
      2008-03-28
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis of flavin-functionalized gold nanoparticles and their catalysis for aerobic hydrogenation2008

    • Author(s)
      Mikiko, Noguchi
    • Organizer
      The 88th Spring Meeting of The Chemical Society of Japan
    • Place of Presentation
      Tokyo
    • Year and Date
      2008-03-28
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] フラビン修飾金ナノ粒子の合成とジイミド還元における触媒能2008

    • Author(s)
      今田泰嗣
    • Organizer
      日本化学会第88春年会
    • Place of Presentation
      立教大学(東京都)
    • Year and Date
      2008-03-28
    • Related Report
      2007 Annual Research Report
  • [Presentation] 環状ニトロンの環拡大メタセシス反応を利用した大環状ポリアミンの合成2007

    • Author(s)
      沖田千明
    • Organizer
      第34有機典型元素化学討論会
    • Place of Presentation
      吹田(大阪大学吹田キャンパス)
    • Year and Date
      2007-12-14
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis of macrocyclic polyamines by ring expansion reaction of cyclic nitrones2007

    • Author(s)
      Chiaki, Okita
    • Organizer
      The 34th Symposium on Main Group Element Chemistry
    • Place of Presentation
      Suita
    • Year and Date
      2007-12-14
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] 環状ニトロンの環拡大メタセシス反応を利用した大環状ポリアミンの合成2007

    • Author(s)
      今田泰嗣
    • Organizer
      第34回有機典型元素化学討論会
    • Place of Presentation
      大阪大学(吹田市)
    • Year and Date
      2007-12-14
    • Related Report
      2007 Annual Research Report
  • [Presentation] デンドリマー-フラビン会合体を触媒とするオレフィンの酸素雰囲気下での水素化反応2007

    • Author(s)
      北川隆啓
    • Organizer
      第40回酸化反応討論会
    • Place of Presentation
      奈良(奈良女子大学)
    • Year and Date
      2007-11-17
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Aerobic Hydrogenation of Olefins with Noncovalently Dendronized Flavin Catalysts2007

    • Author(s)
      Takahiro, Kitagawa
    • Organizer
      The 40th Symposium on Chemical and Biochemical Oxidation
    • Place of Presentation
      Nara
    • Year and Date
      2007-11-17
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] デンドリマー-フラビン会合体を触媒とするオレフィンの酸素雰囲気下での水素化反応2007

    • Author(s)
      今田泰嗣
    • Organizer
      第40回酸化反応討論会
    • Place of Presentation
      奈良女子大学(奈良市)
    • Year and Date
      2007-11-17
    • Related Report
      2007 Annual Research Report
  • [Presentation] Organocatalytic Aerobic Hydrogenation of Olefins2007

    • Author(s)
      Yasushi Imada
    • Organizer
      The 13th Korea-Japan Seminar on Organic Chemistry
    • Place of Presentation
      Daejeon, Korea
    • Year and Date
      2007-10-28
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis and catalysis of flavin-functionalized gold nanoparticles2007

    • Author(s)
      Mikiko, Noguchi
    • Organizer
      The 60th Divisional Meeting on Colloid and Surface Chemistry, the Chemical Society of Japan
    • Place of Presentation
      Matsumoto
    • Year and Date
      2007-09-21
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] フラビン修飾金ナノ粒子の合成とその酸素酸化触媒能2007

    • Author(s)
      野口三紀子
    • Organizer
      第60回コロイドおよび界面化学討論会
    • Place of Presentation
      松本(信州大学旭キャンパス)
    • Year and Date
      2007-09-20
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] フラビン修飾金ナノ粒子の合成とその酸素酸化触媒能2007

    • Author(s)
      今田泰嗣
    • Organizer
      第60回コロイドおよび界面化学討論会
    • Place of Presentation
      信州大学(松本市)
    • Year and Date
      2007-09-20
    • Related Report
      2007 Annual Research Report
  • [Presentation] 電気応答性分子クリップ:環状ビスフラビンのレッドクススイッチングによる分子認識制御2007

    • Author(s)
      大野貴志
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      吹田(関西大学)
    • Year and Date
      2007-03-28
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] フラビン触媒を用いるオレフィンの分子状酸素による水素化反応:デンドリマージアミノピリジンの会合による加速効果2007

    • Author(s)
      北川隆啓
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      吹田(関西大学)
    • Year and Date
      2007-03-28
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] An electric molecular clip : Redox control for binding ability of cyclic bisflavins2007

    • Author(s)
      Takashi, Ohno
    • Organizer
      The 87th Spring Meeting of The Chemical Society of Japan
    • Place of Presentation
      Suita
    • Year and Date
      2007-03-28
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Flavin-catalyzed aerobic hydrogenation of olefins : Acceleration effect of association with dendritic diaminopyridine2007

    • Author(s)
      Takahiro, Kitagawa
    • Organizer
      The 87th Spring Meeting of The Chemical Society of Japan
    • Place of Presentation
      Suita
    • Year and Date
      2007-03-28
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] リボフラビン誘導体を触媒に用いるオレフィンの分子状酸素による水素化反応2007

    • Author(s)
      北川隆啓
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      大阪(関西大学)
    • Year and Date
      2007-03-26
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Aerobic hydrogenation of olefins catalyzed by riboflavin derivatives2007

    • Author(s)
      Takahiro, Kitagawa
    • Organizer
      The 87th Spring Meeting of The Chemical Society of Japan
    • Place of Presentation
      Suita
    • Year and Date
      2007-03-26
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] 環状ビスフラビン化合物のゲスト分子との会合における電気化学的制御2006

    • Author(s)
      大野貴志
    • Organizer
      第36回複素環化学討論会
    • Place of Presentation
      長崎(長崎大学文教キャンパス)
    • Year and Date
      2006-11-24
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Electrochemical control for binding ability of cyclic bisflavin compounds2006

    • Author(s)
      Takashi, Ohno
    • Organizer
      36th Congress of Heterocyclic Chemistry
    • Place of Presentation
      Nagasaki
    • Year and Date
      2006-11-24
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] 環状ニトロンの環拡大反応による大環状ジニトロンの合成2006

    • Author(s)
      沖田千明
    • Organizer
      第36回複素環化学討論会
    • Place of Presentation
      長崎(長崎大学文教キャンパス)
    • Year and Date
      2006-11-23
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis of macrocyclic dinitrones by ring expansion dimerization of cyclic nitrones2006

    • Author(s)
      Chiaki, Okita
    • Organizer
      36th Congress of Heterocyclic Chemistry
    • Place of Presentation
      Nagasaki
    • Year and Date
      2006-11-23
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Aerobic Oxidation of Sulfides Cataltzed by Flavin-Functionalized Gold Nanoparticles2006

    • Author(s)
      Mikiko, Noguchi
    • Organizer
      The 39th Symposium on Chemical and Biochemical Oxidation
    • Place of Presentation
      Tsukuba
    • Year and Date
      2006-11-07
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Organocatalytic Aerobic Hydrogenation of Olefins Catalyzed by Flavin Derivatives2006

    • Author(s)
      Takahiro, Kitagawa
    • Organizer
      The 39th Symposium on Chemical and Biochemical Oxidation
    • Place of Presentation
      Tsukuba
    • Year and Date
      2006-11-07
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] フラビン触媒を用いる分子状酸素によるオレフィンの水素化反応2006

    • Author(s)
      今田泰嗣
    • Organizer
      第39回酸化反応討論会
    • Place of Presentation
      つくば(産総研つくばセンター)
    • Year and Date
      2006-11-06
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] フラビン修飾金ナノ粒子を触媒とするスルフィドの酸素酸化反応2006

    • Author(s)
      野口三紀子
    • Organizer
      第39回酸化反応討論会
    • Place of Presentation
      つくば(産総研つくばセンター)
    • Year and Date
      2006-11-06
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] リボフラビン誘導体を有機分子触媒とするオレフィンの水素化反応2006

    • Author(s)
      北川隆啓
    • Organizer
      第39回酸化反応討論会
    • Place of Presentation
      つくば(産総研つくばセンター)
    • Year and Date
      2006-11-06
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Flavin-Catalyzed Aerobic Hydrogenation of Olefins2006

    • Author(s)
      Yasushi, Imada
    • Organizer
      The 39th Symposium on Chemical and Biochemical Oxidation
    • Place of Presentation
      Tsukuba
    • Year and Date
      2006-11-06
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Book] 有機分子触媒の新展開2006

    • Author(s)
      今田泰嗣
    • Publisher
      シーエムシー出版
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Book] 有機分子触媒の新展開「第21章フラビン分子触媒によるグリーン酸化反応」2006

    • Author(s)
      今田泰嗣(分担執筆)
    • Publisher
      シーエムシー出版
    • Related Report
      2006 Annual Research Report
  • [Patent(Industrial Property Rights)] ヒドラジンを用いた水素化方法および酸素酸化触媒2007

    • Inventor(s)
      今田泰嗣・直田 健
    • Industrial Property Rights Holder
      大阪大学・大阪TLO
    • Industrial Property Number
      2007-061082
    • Filing Date
      2007-03-09
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Patent(Industrial Property Rights)] ヒドラジンを用いた水素化方法および酸素酸化触媒2007

    • Inventor(s)
      今田泰嗣, 直田 健
    • Industrial Property Rights Holder
      大阪大学, 大阪TLO
    • Filing Date
      2007-03-11
    • Related Report
      2006 Annual Research Report
  • [Patent(Industrial Property Rights)] 環状ジニトロン化合物およびその製造方法2006

    • Inventor(s)
      今田泰嗣・直田 健
    • Industrial Property Rights Holder
      大阪大学・日本学術振興機構
    • Filing Date
      2006-09-14
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Overseas

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Published: 2006-04-01   Modified: 2016-04-21  

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