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Development of addtion of C-H bond to simple alkenes and alkynes by iridium catalysts

Research Project

Project/Area Number 24850017
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionTokyo Metropolitan University (2013)
Aoyama Gakuin University (2012)

Principal Investigator

MIURA Hiroki  首都大学東京, 都市環境科学研究科, 助教 (20633267)

Project Period (FY) 2012-08-31 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Fiscal Year 2013: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2012: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords有機金属化学 / イリジウム / C-H活性化 / 単純アルケン / 活性メチレン / カチオン性錯体 / 付加反応 / 1,3-ジケトン
Research Abstract

Addition of carbon-hydrogen bonds to carbon-carbon multiple bond is environmental-benign molecular transformations to afford substituted alkenes with 100% atom-economy. In the present study, cationic iridium catalysts were found to show high activity and selectivity toward the addition of 1,3-dicarbonyl compounds to simple terminal alkenes. Among Ir catalysts examined, [Ir(cod)2]SbF6 showed the highest activity to afford the corresponding products in high yields. Reaction of various terminal alkenes and 1,3-diketones produced the corresponding products in good to high yields.

Report

(3 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Annual Research Report
  • Research Products

    (15 results)

All 2014 2013 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (8 results) Remarks (1 results)

  • [Journal Article] Stereoselective synthesis of either (E) or (Z) silyl enol ether from the same acyclicα,β-unsaturated ketone using cationic rhodium complex-catalyzed 1,4-hydrosilylation2013

    • Author(s)
      G. Onodera, R. Hachisuka, T, Noguchi, H. Miura, T. Hashimoto, R. Takeuchi
    • Journal Title

      Tetarahedron Lett

      Volume: 55 Pages: 310-313

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Ruthenium-Catalyzed intermolecular hydroacylation of internal alkynes; The use of ceria-supported catalyst facilitated the catalyst recycling2013

    • Author(s)
      H. Miura, K. Wada, S. Hosokawa, M. Inoue
    • Journal Title

      Chem. Eur. J

      Volume: 19 Pages: 861-864

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Development of ceria-supported ruthenium catalysts for green organic transformation process2013

    • Author(s)
      K. Wada, H. Miura, S. Hosokawa, M. Inoue
    • Journal Title

      Journal of the Japan Peetroleum Institute

      Volume: 56 Pages: 69-69

    • NAID

      10031166887

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective synthesis of either (E) or (Z) silyl enol ether from the same acyclic α,β-unsaturated ketone using cationic rhodium complex-catalyzed 1,4-hydrosilylation2013

    • Author(s)
      Onodera, Gen; Hachisuka, Ryosuke; Noguchi, Tomomi; Miura, Hiroki; Hashimoto, Toru; Takeuchi, Ryo
    • Journal Title

      Tetrahedron Letter

      Volume: 55 Issue: 2 Pages: 310-313

    • DOI

      10.1016/j.tetlet.2013.10.085

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ruthenium-catalyzed Intermolecular Hydroacylation of Internal Alkynes: The Use of Ceria-supported Catalyst facilitates the Catalyst Recycling2013

    • Author(s)
      Miura, H.; Wada, K.; Hosokawa, S., Inoue, M.
    • Journal Title

      Chem. Eur. J.

      Volume: 19 Issue: 3 Pages: 861-864

    • DOI

      10.1002/chem.201203530

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of Ceria-supported Ruthenium Catalysts for Green Organic Transformation Processes2013

    • Author(s)
      Wada, K.; Miura, H.; Hosokawa, S.; Inoue, M.
    • Journal Title

      Journal of the Japan Petroleum Institute

      Volume: 56 Issue: 2 Pages: 69-79

    • DOI

      10.1627/jpi.56.69

    • NAID

      10031166887

    • ISSN
      1346-8804, 1349-273X
    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Presentation] 酸化物担持Ru触媒による芳香族カルボン酸の内部アルキンへの付加反応2014

    • Author(s)
      筒井健太郎,三浦大樹,和田健司,宍戸哲也
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Year and Date
      2014-03-27
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Presentation] イリジウム触媒を用いたジインとシアナミドの[2+2+2]交差付加環化反応2013

    • Author(s)
      橋本徹,石井悟,三浦大樹,坂田健,武内亮
    • Organizer
      第66回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      東京工業大学・大岡山キャンパス
    • Year and Date
      2013-11-30
    • Related Report
      2013 Final Research Report
  • [Presentation] イリジウム触媒による1,3-ジケトンの単純末端アルケンへの位置選択的付加反応2013

    • Author(s)
      橋本徹,佐川潤,三浦大樹,武内亮
    • Organizer
      第3回CSJ化学フェスタ2013
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2013-10-21
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Presentation] イリジウム触媒を用いたα,ω-ジインとシアナミドの[2+2+2]環化付加反応2013

    • Author(s)
      橋本徹,石井悟,三浦大樹,坂田健,武内亮
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      学習院大学
    • Year and Date
      2013-09-12
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Presentation] イリジウム触媒を用いたジインとシアナミドの[2+2+2]交差付加環化反応2013

    • Author(s)
      橋本徹・ 石井悟史・三浦大樹・坂田健・武内亮
    • Organizer
      第66回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      東京工業大学 大岡山キャンパス
    • Related Report
      2013 Annual Research Report
  • [Presentation] Iridium-Catalyzed Cycloaddition of α,ω-Diynes with Nitriles:Efficient Synthesis of Oligoheteroarenes2013

    • Author(s)
      Ryo Takeuchi, Gen Onodera, Hiroki Miura, Toru Hashimoto, Yukiko Ebihara, Shun Yamazaki, Yoshihisa Shimizu
    • Organizer
      Nagoya Symposium 2013
    • Place of Presentation
      Nagoya University
    • Related Report
      2013 Annual Research Report
  • [Presentation] Efficient Synthesis of Oligoheteroarenes by Iridium-Catalyzed [2+2+2] Cycloaddition of Diynes with Nitriles2013

    • Author(s)
      Toru Hashimoto, Yukiko Ebihara, Yoshihisa Shimizu, Gen Onodera, Hiroki Miura, Ryo Takeuchi
    • Organizer
      10th International symposium on carbanion chemistry ISCC-10
    • Place of Presentation
      Doshisha University
    • Related Report
      2013 Annual Research Report
  • [Presentation] イリジウム触媒による1,3-ジケトンの単純末端アルケンへの位置選択的付加反応2013

    • Author(s)
      三浦大樹・佐川潤・武内亮
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://www.comp.tmu.ac.jp/shishidolab/

    • Related Report
      2013 Final Research Report

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Published: 2012-11-27   Modified: 2019-07-29  

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