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Site-selective hydrogen abstraction of hydrocarbons by sterically hindered organocatalyst

Research Project

Project/Area Number 17K14487
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionOsaka Prefecture University

Principal Investigator

ueda mitsuhiro  大阪府立大学, 理学(系)研究科(研究院), 講師 (60566298)

Research Collaborator Morisaki Takahiro  
Kagiyama Hiroki  
Project Period (FY) 2017-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2018: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2017: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywordsペルオキソ二硫酸塩 / 位置選択的官能基化 / 低環境負荷型有機合成反応 / 脂肪族飽和炭化水素 / 四級アンモニウムカチオン / 環状ケトン / ペルオキソ二硫酸アニオン / 四級ホスホニウム塩 / 有機化学
Outline of Final Research Achievements

I challenged the development of efficient transformation to important carbon compounds of cheap hydrocarbons. As the result, I developed the site-selective vinylation of cyclic ketones with trans-1,2-bis(phenylsulfonyl)ethylene in the presence of potassium peroxodisulfate.

Academic Significance and Societal Importance of the Research Achievements

本研究期間内に開発した反応は、安全かつ安価なペルオキソ二硫酸塩をラジカル発生試薬として用い、主溶媒として水を用いていることから、環境に優しいグリーンな反応である。また、本反応では貴重な炭素資源をより高付加価値な炭素化合物へ非常に効率良く変換することが出来る。これらの特徴は、現代の社会が求める低環境負荷かつ低消費エネルギーでのものづくりというキーワードに合致しており、本研究期間内に開発した反応の社会的意義は高い。

Report

(3 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • Research Products

    (12 results)

All 2019 2017

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (6 results) (of which Int'l Joint Research: 3 results)

  • [Journal Article] Transition-Metal-Catalyst-Free Cross-Coupling Reaction of Secondary Propargylic Acetates with Alkenyl- and Arylboronic Acids2017

    • Author(s)
      Ueda, M.; Nakakoji, D.; Morisaki, T.; Ryu, I.
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2017 Issue: 47 Pages: 7040-7045

    • DOI

      10.1002/ejoc.201701450

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Cobalt-Catalyzed Regioselective [3+2] Annulation of ortho-Formyl and Acetyl Substituted Phenylboronic Acids with Alkynes2017

    • Author(s)
      Ueda, M.; Ueno, T.; Suyama, Y.; Ryu, I.
    • Journal Title

      Tetrahedron Lett.

      Volume: 58 Issue: 30 Pages: 2972-2974

    • DOI

      10.1016/j.tetlet.2017.06.049

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Ammonium Chiral Borate Salt Catalyzed Asymmetric Friedel-Crafts Alkylation of Indoles with ,-Disubstituted Enals2017

    • Author(s)
      Ueda, M.; Yagyu, Y.; Ryu, I.
    • Journal Title

      Tetrahedron: Asymmetry

      Volume: 28 Issue: 8 Pages: 1070-1077

    • DOI

      10.1016/j.tetasy.2017.06.003

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Scalable Flow Synthesis of [6,6]-Phenyl-C61-Butyric Acid Methyl Ester (PCBM) using a Flow Photoreactor with a Sodium Lamp2017

    • Author(s)
      Ueda, M.; Imai, N.; Yoshida, S.; *Yasuda, H.; *Fukuyama, T.; Ryu, I.
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2017 Issue: 44 Pages: 6483-6485

    • DOI

      10.1002/ejoc.201700745

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Bromoallylation of Alkenes Leading to 4-Alkenyl Bromides Based on Trapping of -Bromoalkyl Radicals2017

    • Author(s)
      Kippo, T.; Hamaoka, K.; Ueda, M.; Fukuyama, T.; Ryu. I.
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 19 Pages: 5189-5200

    • DOI

      10.1021/acs.orglett.7b02471

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Bromine-Radical-Mediated Synthesis of -Functionalized ,- and ,-Unsaturated Ketones via C-H Functionalization of Aldehydes2017

    • Author(s)
      Kippo, T.; Kimura, Y.; Ueda, M.; Fukuyama, T.; Ryu, I
    • Journal Title

      Synlett

      Volume: 28 Issue: 14 Pages: 1733-1737

    • DOI

      10.1055/s-0036-1588494

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] ペルオキソ二硫酸塩を用いた環状ケトンの位置選択的C-Hビニル化反応2019

    • Author(s)
      上川 和也、植田 光洋、福山 高英、柳 日馨
    • Organizer
      日本化学会第99春季年会2019
    • Related Report
      2018 Annual Research Report
  • [Presentation] [2+2] Cycloadditions of 1,3-Bifunctional Allenes with C602017

    • Author(s)
      橋下 拓幸、端山 美帆、棟近 愛子、植田 光洋、柳 日馨
    • Organizer
      The 11th International Symposium on Integrated Synthesis
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] [2+2] Cycloadditions of 1,3-Bifunctional Allenes with C60 by using a Flow Reaction System2017

    • Author(s)
      橋下 拓幸、端山 美帆、棟近 愛子、植田 光洋、柳 日馨
    • Organizer
      The First International Conference on Automated Flow and Microreactor Synthesis(ICAMS-1)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Potassium Substituted Halomethyltrifluoroborates by Atom-Transfer Radical Addition to Potassium Vinyltrifluoroborates2017

    • Author(s)
      森崎雄大、植田光洋、柳日馨
    • Organizer
      The 11th International Symposium on Integrated Synthesis
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] 原子移動型ラジカル反応を利用した極性官能基含有第二級アルキルホウ素化合物の合成2017

    • Author(s)
      森崎雄大、植田光洋、柳日馨
    • Organizer
      第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 高機能有機薄膜太陽電池開発のための新規フラーレン誘導体の開発2017

    • Author(s)
      植田 光洋, 坂口 司, 端山 美帆, 柳 日馨
    • Organizer
      第6回 JACI/GSC シンポジウム
    • Related Report
      2017 Research-status Report

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Published: 2017-04-28   Modified: 2020-03-30  

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