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Development and application of novel bond formation reactions of heteroaromatic compounds via iodonium intermediates.

Research Project

Project/Area Number 21890280
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionRitsumeikan University

Principal Investigator

MORIMOTO Koji  Ritsumeikan University, 立命館グローバル・イノベーション機構, ポストドクトラルフェロー (10543952)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥2,652,000 (Direct Cost: ¥2,040,000、Indirect Cost: ¥612,000)
Fiscal Year 2010: ¥1,261,000 (Direct Cost: ¥970,000、Indirect Cost: ¥291,000)
Fiscal Year 2009: ¥1,391,000 (Direct Cost: ¥1,070,000、Indirect Cost: ¥321,000)
Keywords有機化学 / ヘテロ芳香族 / 超原子価ヨウ素 / ビアリール / ヘテロ芳香族化合物 / ヨードニウム塩 / クロスカップリング / ヘテロ芳香族ビアリール類 / Head to Tail / 機能性材料 / 抗腫瘍活性天然物 / 生理活性天然物
Research Abstract

Biaryl compounds are versatile building blocks in the synthesis of natural products, pharmaceuticals, agricultural chemicals and π-conjugated organic materials. Therefore, the development of convenient cross-coupling reaction for giving biaryls is one of the important subjects in organic chemistry.
I have developed the biaryl cross-coupling reaction of heteroaromatic compounds via diaryl iodonium salts, leading to various heterobiaryls. In addition, we also developed a metal-free regioselective oxidative synthesis of head-to-tail (H-T) bithiophenes using hypervalent iodine (III) reagent. This unique unsymmetrical coupling reaction was realized through the iodonium intermediate for the switching reactivity of 3-substituted thiophenes, and exclusive nucleophilicity of the neutral 3-substituted thiophenes at the 2-position.

Report

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

    (21 results)

All 2010 2009 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (14 results) Remarks (1 results)

  • [Journal Article] Metal-free regioselective oxidative biaryl coup ling leading to head-to-tail bithiophenes : Reactivity switching, a concept based on the iodonium(III) intermediate.2010

    • Author(s)
      Morimoto Koji; Yamaoka Nobutaka; Ogawa Chieko; Nakae Tomofumi; Fujioka Hiromichi; Dohi Toshifumi; Kita Yasuyuki
    • Journal Title

      Org.Lett. 12(IF:5.1)

      Pages: 3804-3807

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Unusual ipso Substitution of Diaryliodonium Bromides Initiated by a Single-Electron-Transfer Oxidizing Process.2010

    • Author(s)
      Dohi Toshifumi; Ito Motoki; Yamaoka Nobutaka; Morimoto Koji; Fujioka Hiromichi; Kita Yasuyuki
    • Journal Title

      Angew.Chem.Int.Ed. 49(IF:11.8)

      Pages: 3334-3337

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Metal-free regioselective oxidative biaryl coupling leading to head-to-tail bithiophenes : Reactivity switching, a concept based on the iodonium(III) intermediate2010

    • Author(s)
      森本功治、土肥寿文、北泰行, 他
    • Journal Title

      Org.Lett.

      Volume: 12 Pages: 3804-3807

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Unusual ipso Substitution of Diaryliodonium Bromides Initiated by a Single-Electron-Transfer Oxidizing Process.2010

    • Author(s)
      土肥寿文、森本功治、北泰行, 他
    • Journal Title

      Angew. Chem. Int Ed.

      Volume: 49 Pages: 3334-3337

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hypervalent iodine(III) : selective and efficient single-electron-transfer (SET) oxidizing agent.2009

    • Author(s)
      Dohi Toshifumi; Ito Motoki; Yamaoka Nobutaka; Morimoto Koji; Fujioka Hiromichi; Kita Yasuyuki
    • Journal Title

      Tetrahedron, (Account of Special Issue) 65(IF:2.9)

      Pages: 10797-10797

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Hypervalent iodine(III) : selective and efficient single-electron-transfer(SET)oxidizing agent2009

    • Author(s)
      土肥寿文、伊藤元気、山岡信貴、森本功治、藤岡弘道、北泰行
    • Journal Title

      Tetrahedron, Elsevier 65

      Pages: 10797-10815

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] Metal-free direct biaryl coupling reaction of heteroaromatic compounds viaiodonium intermediate2010

    • Author(s)
      森本功治
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawai
    • Year and Date
      2010-12-19
    • Related Report
      2010 Annual Research Report
  • [Presentation] 超原子価ヨウ素中間体を経由する効率的ヘテロ芳香族ビアリール類合成2010

    • Author(s)
      森本功治
    • Organizer
      第36回反応と合成の進歩シンポジウム
    • Place of Presentation
      ウインクあいち(愛知県産業労働センター)(愛知県)
    • Year and Date
      2010-11-02
    • Related Report
      2010 Annual Research Report
  • [Presentation] 超原子価ヨウ素反応剤を用いたフェノール類からのオルトスピロラクトン骨格構築法2010

    • Author(s)
      森本功治、仲江朋史、畑佳世子、Simon B.Cmmerer、土肥寿文、北泰行
    • Organizer
      第60回日本薬学会近畿支部総会・大会
    • Place of Presentation
      摂南大学(大阪府)(口頭発表)
    • Year and Date
      2010-10-30
    • Related Report
      2010 Final Research Report
  • [Presentation] 遷移金属触媒を用いないヘテロ芳香族化合物のクロスカップリング反応の開発-ヘテロ芳香族ヨードニウム中間体の反応性の解明-2010

    • Author(s)
      森本功治、山岡信貴、仲江朋史、石角陽平、土肥寿文、北泰行
    • Organizer
      第60回日本薬学会近畿支部総会・大会
    • Place of Presentation
      摂南大学(大阪府)(口頭発表)
    • Year and Date
      2010-10-30
    • Related Report
      2010 Final Research Report
  • [Presentation] 遷移金属触媒を用いないヘテロ芳香族化合物のクロスカップリング反応の開発-ヘテロ芳香族ヨードニウム中間体の反応性の解明-2010

    • Author(s)
      森本功治
    • Organizer
      第60回 日本薬学会近畿支部総会・大会
    • Place of Presentation
      摂南大学(大阪府)
    • Year and Date
      2010-10-30
    • Related Report
      2010 Annual Research Report
  • [Presentation] 芳香族ヨードニウム塩の新規イプソ置換反応2010

    • Author(s)
      森本功治、山岡信貴、伊藤元気、仲江朋史、藤岡弘道、土肥寿文、北泰行
    • Organizer
      第130回日本薬学会年会
    • Place of Presentation
      岡山大学(岡山県)(口頭発表)
    • Year and Date
      2010-03-28
    • Related Report
      2010 Final Research Report
  • [Presentation] Metal-free direct biaryl coupling reaction of heteroaromatic compounds via iodonium intermediate2010

    • Author(s)
      森本功治
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii(poster presentation)
    • Related Report
      2010 Final Research Report
  • [Presentation] 超原子価ヨウ素中間体を経由する効率的ヘテロ芳香族ビアリール類合成2010

    • Author(s)
      森本功治、山岡信貴、仲江朋文、石角陽平、土肥寿文、北泰行
    • Organizer
      第36回反応と合成の進歩シンポジウム
    • Place of Presentation
      ウインクあいち(愛知県産業労働センター)(愛知県)(ポスター発表)
    • Related Report
      2010 Final Research Report
  • [Presentation] ヨードニウム塩の新規活性化法を鍵とするヘテロ芳香族ビアリール合成2009

    • Author(s)
      森本功治、山岡信貴、仲江朋史、土肥寿文、北泰行
    • Organizer
      第59回日本薬学会近畿支部総会・大会
    • Place of Presentation
      近畿大学(大阪府)(口頭発表)
    • Year and Date
      2009-10-24
    • Related Report
      2010 Final Research Report
  • [Presentation] 超原子価ヨウ素反応剤を用いた含ヘテロ芳香族ビアリール類の効率的合成法2009

    • Author(s)
      土肥寿文、小川智恵子、伊藤元気、森本功治、藤岡弘道、北泰行
    • Organizer
      第39回複素環化学討論会
    • Place of Presentation
      さわやかちば県民プラザ(千葉県)(ポスター発表)
    • Year and Date
      2009-10-15
    • Related Report
      2010 Final Research Report
  • [Presentation] 金属触媒を用いないヘテロ芳香族化合物の新規酸化的カップリング反応2009

    • Author(s)
      森本功治、伊藤元気、小川智恵子、山岡信貴、藤岡弘道、土肥寿文、北泰行
    • Organizer
      第7回次世代シンポジウム
    • Place of Presentation
      大阪大学(大阪府)(口頭発表)
    • Year and Date
      2009-07-23
    • Related Report
      2010 Final Research Report
  • [Presentation] Metal-free biaryl coupling reaction of heteroaromatic compounds using hypervalent iodine(III) reagent2009

    • Author(s)
      Koji Morimoto, Motoki Ito, Chieko Ogawa, Hiromichi Fujioka, ToshifumiDohi, Yasuyuki Kita
    • Organizer
      22^<nd> International Congress on Heterocyclic Chemistry
    • Place of Presentation
      St. John's, Canada(poster presentation)
    • Related Report
      2010 Final Research Report
  • [Presentation] Metal free biaryl coupling reaction of heteroaromatic compounds using hypervalent iodine(III)reagent2009

    • Author(s)
      Koji Morimoto, Motoki Ito, Chieko Ogawa, Hiromichi Fujioka, Toshifumi Dohi, Yasuyuki Kita
    • Organizer
      22th International Congress of Heterocyclic Chemistry
    • Place of Presentation
      Canada-St.John's
    • Related Report
      2009 Annual Research Report
  • [Presentation] 金属触媒を用いないヘテロ芳香族化合物の新規酸化的カップリング反応2009

    • Author(s)
      森本功治、伊藤元気、小川智恵子、山岡信貴、藤岡弘道、土肥寿文、北泰行
    • Organizer
      第7回次世代を担う有機化学シンポジウム
    • Place of Presentation
      大阪府吹田市 大阪大学コンベンションセンター
    • Related Report
      2009 Annual Research Report
  • [Remarks] ホームページ等

    • Related Report
      2010 Final Research Report

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

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