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Synthesis of Substituted Benzene Derivatives through Dehydrogenative Carbon-Carbon Formation between Aliphatic and Aromatic Compounds

Research Project

Project/Area Number 26620082
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionKwansei Gakuin University (2015)
Kyoto University (2014)

Principal Investigator

Shirakawa Eiji  関西学院大学, 理工学部, 教授 (70273472)

Project Period (FY) 2014-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2014: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywordsラジカル反応 / 芳香族置換反応 / 有機合成化学
Outline of Final Research Achievements

Utilizing homolytic aromatic substitution mechanism consisting of addition of a radical species to aromatic rings and elimination of another radical species, we have accomplished, with the aid of tert-butoxy radical precursors, the dehydrogenative coupling between amides/ureas/ethers and benzene derivatives as well as the alpha-arylation of amines with aryl halides or sulfones. A simple reduction system of aryl halides consisting of cesium carbonate, isopropyl alcohol and a tert-butoxy radical precursor also has been developed.

Report

(3 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • Research Products

    (9 results)

All 2016 2015 2014

All Journal Article (2 results) (of which Peer Reviewed: 2 results,  Open Access: 2 results,  Acknowledgement Compliant: 2 results) Presentation (7 results)

  • [Journal Article] Reduction of Aryl Halides into Arenes with 2-Propanol Promoted by a Stoichiometric Amount of a tert-Butoxy Radical Source2016

    • Author(s)
      Ryota Ueno, Takashi Shimizu, Eiji Shirakawa
    • Journal Title

      Synlett

      Volume: 27 Issue: 05 Pages: 741-744

    • DOI

      10.1055/s-0035-1561342

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Base-promoted dehydrogenative coupling of benzene derivatives with amides or ethers2014

    • Author(s)
      上野遼太,白川英二
    • Journal Title

      Organic and Biomolecular Chemistry

      Volume: 12 Issue: 38 Pages: 7469-7473

    • DOI

      10.1039/c4ob01253d

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] tert-ブトキシラジカルによって引き起こされるスルホニルアレーンを用いるアミンのα-アリール化反応2016

    • Author(s)
      池田佑子,上野遼太,白川英二
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] tert-ブトキシラジカル源によって促進されるハロゲン化アリールによる脂肪族アミンのα-アリール化反応2015

    • Author(s)
      上野遼太,白川英二
    • Organizer
      第35回有機合成若手セミナー
    • Place of Presentation
      京都府立大学(京都府京都市)
    • Year and Date
      2015-08-01
    • Related Report
      2015 Annual Research Report
  • [Presentation] 過酸化物によって促進されるハロゲン化アリールによる脂肪族アミンのα-アリール化反応2015

    • Author(s)
      上野遼太,白川英二
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] 過酸化物によって促進される2-プロパノールを用いたハロゲン化アリールの還元反応2015

    • Author(s)
      清水 駿,上野遼太,白川英二
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] ナトリウムアレニドを鍵中間体とするアレーンと脂肪族化合物の脱水素カップリング反応2014

    • Author(s)
      上野遼太,白川英二
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Research-status Report
  • [Presentation] Base-Promoted Dehydrogenative Coupling of Benzene Derivatives with Amides or Ethers2014

    • Author(s)
      R. Ueno, E. Shirakawa
    • Organizer
      XXVI International Conference on Organometallic Chemistry
    • Place of Presentation
      Royton Sapporo
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Research-status Report
  • [Presentation] 強塩基と酸化剤を用いるアレーンと脂肪族の脱水素カップリング反応2014

    • Author(s)
      上野遼太,白川英二
    • Organizer
      第3回JACI/GSCシンポジウム
    • Place of Presentation
      東京国際フォーラム
    • Year and Date
      2014-05-22 – 2014-05-23
    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2017-05-10  

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