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Development and application of multi-functional hybrid-type organocatalysts based on hypervalent iodine oxidation

Research Project

Project/Area Number 21590005
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionUniversity of Toyama

Principal Investigator

YAKURA Takayuki  富山大学, 大学院・医学薬学研究部(薬学), 教授 (70220126)

Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2011: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2010: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2009: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords超原子価ヨウ素 / 酸化 / ハイブリッド / 有機触媒 / ニトロキシルラジカル
Research Abstract

A novel hybrid-type organocatalyst having two deferent catalytic sites, 2, 2, 6, 6-tetramethyl-1-piperidinyloxyl(TEMPO) and iodobenzene sites, was developed and applied the oxidation of alcohols. The two catalytic sites were connected by ester bonds with phthalic acid as a linker. The reaction of primary alcohols with the catalyst in the presence of peracetic acid as a co-oxidant was smoothly proceeded to give the corresponding carboxylic acid in excellent yield.

Report

(4 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • 2009 Annual Research Report
  • Research Products

    (39 results)

All 2011 2010 2009

All Journal Article (11 results) (of which Peer Reviewed: 6 results) Presentation (24 results) Patent(Industrial Property Rights) (4 results) (of which Overseas: 1 results)

  • [Journal Article] Novel 2, 2, 6, 6-tetramethylpiperidine-1-oxyl-iodobenzene hybrid catalyst for oxidation of primary alcohols to carboxylic acids2011

    • Author(s)
      Yakura T. and Ozono A.
    • Journal Title

      Adv. Synth. Catal.

      Volume: 353 Pages: 855-859

    • Related Report
      2011 Final Research Report
  • [Journal Article] An efficient catalytic oxidation of p-alkoxypenols to p-quinones using tetrabutylammonium bromide and Oxone^[○! R]2011

    • Author(s)
      Yakura T., Ozono A., and Morimoto K.
    • Journal Title

      Chem. Pharm. Bull

      Volume: 59 Pages: 132-134

    • Related Report
      2011 Final Research Report
  • [Journal Article] Novel 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-iodobenzene hybrid catalyst for oxidation of primary alcohols to carboxylic acids2011

    • Author(s)
      Takayuki Yakura, Ayaka Ozono
    • Journal Title

      Adv.Synth.Catal.

      Volume: 353 Pages: 181-185

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] An efficient catalytic oxidation of p-alkoxypenols to p-quinones using tetrabut lammonium bromide and Oxone^(R)2011

    • Author(s)
      Takayuki Ykura
    • Journal Title

      Chem.Pharm.Bull.

      Volume: 59 Pages: 132-134

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Novel 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-iodobenzene hybrid catalyst for oxidation of primary alcohols to carboxylic acids2011

    • Author(s)
      Takayuki Ykura
    • Journal Title

      Adv.Synth.Catal.

      Volume: 353(印刷中)

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hypervalent iodine oxidation of phenol derivatives using a catalytic amount of 4-iodophenoxyacetic acid and Oxone^[○! R] as a co-oxidant2010

    • Author(s)
      Yakura T., Omoto M., Yamauchi Y., Tian Y., and Ozono A.
    • Journal Title

      Tetrahedron

      Volume: 66 Pages: 5833-5840

    • Related Report
      2011 Final Research Report
  • [Journal Article] Hypervalent iodine oxidation of phenol derivatives using a catalytic amount of 4-iodo henox acetic acid and Oxone^(R) as a co-oxidant2010

    • Author(s)
      Takayuki Ykura
    • Journal Title

      Tetrahedron

      Volume: 66 Pages: 5833-5840

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Efficient synthesis of p-quinols using catalytic hypervalent iodine oxidation of 4-arylphenols with 4-iodophenoxyacetic acid and Oxone2009

    • Author(s)
      Yakura T. and Omoto M.
    • Journal Title

      Chem. Pharm. Bull

      Volume: 57 Pages: 643-645

    • NAID

      130000124359

    • Related Report
      2011 Final Research Report
  • [Journal Article] Catalytic hypervalent iodine oxidation using 4-phenoxyacetic acid and Oxone : Oxidation of p-alkoxyphenols to p-benzoquinones2009

    • Author(s)
      Yakura T., Tian Y., Yamauchi Y., Omoto M., and Konishi T.
    • Journal Title

      Chem. Pharm. Bull

      Volume: 57 Pages: 252-256

    • Related Report
      2011 Final Research Report
  • [Journal Article] Catalytic hypervalent iodine oxidation using 4-phenoxyacetic acid and Oxone : Oxidation of p-alkoxyphenols to p-benzoquinones2009

    • Author(s)
      Takayuki Yakura
    • Journal Title

      Chem.Pharm.Bull. 57

      Pages: 252-256

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Efficient synthesis of p-quinols using catalytic hypervalent iodine oxidation of 4-arylphenols with 4-iodophenoxyacetic acid and Oxone2009

    • Author(s)
      Takayuki Yakura
    • Journal Title

      Chem.Pharm.Bull. 57

      Pages: 643-645

    • NAID

      130000124359

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] 2,2,6,6-Tetramethyl-piperidine-1-oxyl (TEMPO)-iodobenzene hybrid : Anovel bifunctional catalyst for oxidation of alcohols2011

    • Author(s)
      Takayuki Yakura, Ayaka Ozono, Narumi Noda
    • Organizer
      8th AFMC International Medicinal Chemistry Symposium
    • Place of Presentation
      KEIO PLAZA HOTEL TOKYO (Tokyo)
    • Year and Date
      2011-12-01
    • Related Report
      2011 Annual Research Report
  • [Presentation] 超原子価ヨウ素酸化を基盤とするハイブリッド型酸化触媒の創製とアルコール酸化反応2011

    • Author(s)
      矢倉隆之,大園綾香,野田成美
    • Organizer
      第14回ヨウ素学会シンポジウム
    • Place of Presentation
      千葉
    • Year and Date
      2011-11-18
    • Related Report
      2011 Final Research Report
  • [Presentation] 超原子価ヨウ素酸化を基盤とするハイブリッド型酸化触媒の創製とアルコール酸化反応2011

    • Author(s)
      矢倉隆之, 大園綾香, 野田成美
    • Organizer
      第14回ヨウ素学会シンポジウム
    • Place of Presentation
      千葉大学(千葉)
    • Year and Date
      2011-11-18
    • Related Report
      2011 Annual Research Report
  • [Presentation] ハイブリッド型酸化触媒の設計と反応性の検討2011

    • Author(s)
      大園綾香, 野田成美, 矢倉隆之
    • Organizer
      平成23年度有機合成化学北陸セミナー
    • Place of Presentation
      港のホテル(あわら,福井)
    • Year and Date
      2011-10-07
    • Related Report
      2011 Annual Research Report
  • [Presentation] TEMPO-iodobenzene hybrid catalyst for environmentally benign oxidation of alcohols2011

    • Author(s)
      Takayuki Yakura, Ayaka Ozono
    • Organizer
      The 23^<rd> International Congress on Heterocyclic Chemistry
    • Place of Presentation
      Scottish Exhibition and Conference Centre, Glasgow (Scotland)
    • Year and Date
      2011-08-02
    • Related Report
      2011 Annual Research Report
  • [Presentation] TEMPO-iodobenzeneハイブリッド触媒の合成とその利用2011

    • Author(s)
      大園綾香, 矢倉隆之
    • Organizer
      第9回次世代を担う有機化学シンポジウム
    • Place of Presentation
      日本薬学会長井記念ホール(東京)
    • Year and Date
      2011-05-27
    • Related Report
      2011 Annual Research Report
  • [Presentation] TEMPO-iodobenzeneハイブリッド触媒を用いる第1級アルコール類のカルボン酸類への酸化反応2011

    • Author(s)
      矢倉隆之
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      ツインメッセ静岡(静岡)
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] 2, 2, 6, 6-Tetramethyl-piperidine-1-oxyl(TEMPO)-iodobenzene hybrid : A novel bifunctional catalyst for oxidation of alcohols2011

    • Author(s)
      Yakura T., Ozono A., and Noda N.
    • Organizer
      8th AFMC International Medicinal Chemistry Symposium
    • Place of Presentation
      Tokyo
    • Related Report
      2011 Final Research Report
  • [Presentation] ハイブリッド型酸化触媒の設計と反応性の検討2011

    • Author(s)
      大園綾香,野田成美,矢倉隆之
    • Organizer
      平成23年度有機合成化学北陸セミナー
    • Place of Presentation
      あわら(福井)
    • Related Report
      2011 Final Research Report
  • [Presentation] TEMPO-iodobenzene hybrid catalyst for environmentally benign oxidation of alcohols2011

    • Author(s)
      Yakura T. and Ozono A.
    • Organizer
      The 23^<rd> International Congress on Heterocyclic Chemistry
    • Place of Presentation
      Glasgow(Scotland)
    • Related Report
      2011 Final Research Report
  • [Presentation] TEMPO-iodobenzeneハイブリッド触媒の合成とその利用2011

    • Author(s)
      大園綾香,矢倉隆之
    • Organizer
      第9回次世代を担う有機化学シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2011 Final Research Report
  • [Presentation] テトラブチルアンモニウムブロミド-オキソンを用いるp-アルコキシフェノール類のp-キノン類への酸化反応2011

    • Author(s)
      矢倉隆之,大園綾香,森本晃平
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Related Report
      2011 Final Research Report
  • [Presentation] TEMPO-iodobenzeneハイブリッド触媒を用いる第1級アルコール類のカルボン酸類への酸化反応2011

    • Author(s)
      矢倉隆之,大園綾香
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Related Report
      2011 Final Research Report
  • [Presentation] Synthesis of p-quinones using catalytic hypervalent iodine oxidation of p-dialkyoxyarenes2010

    • Author(s)
      Takayuki Yakura
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2010-12-17
    • Related Report
      2010 Annual Research Report
  • [Presentation] TEMPOおよび超原子価ヨウ素酸化を基盤とするハイブリッド型酸化触媒の創製と反応2010

    • Author(s)
      大園綾香,矢倉隆之
    • Organizer
      日本薬学会北陸支部第122回例会
    • Place of Presentation
      金沢
    • Year and Date
      2010-11-21
    • Related Report
      2011 Final Research Report
  • [Presentation] TEMPOおよび超原子価ヨウ素酸化を基盤とするハイブリッド型酸化触媒の創製と反応2010

    • Author(s)
      矢倉隆之
    • Organizer
      日本薬学会北陸支部第122回例会
    • Place of Presentation
      北陸大学(金沢)
    • Year and Date
      2010-11-21
    • Related Report
      2010 Annual Research Report
  • [Presentation] TEMPOおよびヨードアレーンを触媒とする第1級アルコール類のカルボン酸への直接酸化反応2010

    • Author(s)
      矢倉隆之,大園綾香,齋藤健太郎,牛文起
    • Organizer
      第13回ヨウ素学会シンポジウ
    • Place of Presentation
      千葉
    • Year and Date
      2010-11-09
    • Related Report
      2011 Final Research Report
  • [Presentation] TEMPOおよびヨードアレーンを触媒とする第1級アルコール類のカルボン酸への直接酸化反応2010

    • Author(s)
      矢倉隆之
    • Organizer
      第13回ヨウ素学会シンポジウム
    • Place of Presentation
      千葉大学(千葉)
    • Year and Date
      2010-11-09
    • Related Report
      2010 Annual Research Report
  • [Presentation] TEMPO-ヨードベンゼン-過酢酸を用いるアルコール類の新規二重触媒酸化反応2010

    • Author(s)
      矢倉隆之
    • Organizer
      平成22年度有機合成化学北陸セミナー
    • Place of Presentation
      石川県青少年総合研修センター(金沢)
    • Year and Date
      2010-10-08
    • Related Report
      2010 Annual Research Report
  • [Presentation] Synthesis of p-quinones using catalytic hypervalent iodine oxidation of p-dialkyoxyarenes2010

    • Author(s)
      Yakura T., Ozono A., Yamauchi Y., and Tian Y.
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu(USA)
    • Related Report
      2011 Final Research Report
  • [Presentation] TEMPO-ヨードベンゼン-過酢酸を用いるアルコール類の新規二重触媒酸化反応2010

    • Author(s)
      矢倉隆之,大園綾香,齋藤健太郎,牛文起
    • Organizer
      平成22年度有機合成化学北陸セミナー
    • Place of Presentation
      金沢
    • Related Report
      2011 Final Research Report
  • [Presentation] 4-ヨードフェノキシ酢酸-オキソン系を用いるフェノール類の触媒的酸化反応2009

    • Author(s)
      矢倉隆之
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢市文化ホール(金沢市)
    • Year and Date
      2009-11-17
    • Related Report
      2009 Annual Research Report
  • [Presentation] 4-ヨードフェノキシ酢酸-オキソン系を用いるフェノール類の触媒的酸化反応2009

    • Author(s)
      矢倉隆之,小西達也,山内優,田園,大本真徳
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢
    • Related Report
      2011 Final Research Report
  • [Presentation] 4-ヨードフェノキシ酢酸-オキソン系を用いる触媒的超原子価ヨウ素酸化反応: p-ジアルコキシベンゼン類からp-キノン類の合成2009

    • Author(s)
      矢倉隆之,田園,山内優,大本真徳
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都
    • Related Report
      2011 Final Research Report
  • [Patent(Industrial Property Rights)] 有機ハイブリッド型触媒2011

    • Inventor(s)
      矢倉隆之,大園綾香
    • Industrial Property Rights Holder
      富山大学
    • Filing Date
      2011-11-01
    • Related Report
      2011 Final Research Report
  • [Patent(Industrial Property Rights)] 有機ハイブリッド型触媒2011

    • Inventor(s)
      矢倉隆之, 大園綾香
    • Industrial Property Rights Holder
      富山大学
    • Filing Date
      2011-11-01
    • Related Report
      2011 Annual Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] 有機ハイブリッド型触媒2010

    • Inventor(s)
      矢倉隆之,大園綾香
    • Industrial Property Rights Holder
      富山大学
    • Filing Date
      2010-11-04
    • Related Report
      2011 Final Research Report
  • [Patent(Industrial Property Rights)] 有機ハイブリッド型触媒2010

    • Inventor(s)
      矢倉隆之, 大園綾香
    • Industrial Property Rights Holder
      富山大学
    • Industrial Property Number
      2010-247803
    • Filing Date
      2010-11-04
    • Related Report
      2010 Annual Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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