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Development of synthetic method of phenol cross-coupling products by using quinone derivatives

Research Project

Project/Area Number 16H07340
Research Category

Grant-in-Aid for Research Activity Start-up

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

Principal Investigator

Kamitanaka Tohru  立命館大学, 総合科学技術研究機構, 助教 (70783794)

Project Period (FY) 2016-08-26 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsキノンモノアセタール / フェノール / カップリング / ブレンステッド酸 / 有機化学 / ジベンゾフラン / クロスカップリング
Outline of Final Research Achievements

We have developed the synthetic method of phenol cross-coupling products by the introduction of phenols into quinone monoacetals (QMAs). This method can efficiently provide the regioselectively connected products by the activation of acetal moiety on QMAs under mild condition. Moreover, we have presented that this reaction proceeds by the nucleophilic substitution mechanism and can be applied for various nucleophiles. Furthermore, useful skeletons, such as phenol-trimer and dibenzofuran, could be constructed by the applicable methods from phenol cross-coupling products.

Report

(3 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Annual Research Report
  • Research Products

    (8 results)

All 2018 2017 2016

All Journal Article (2 results) (of which Peer Reviewed: 2 results,  Acknowledgement Compliant: 1 results) Presentation (6 results) (of which Int'l Joint Research: 1 results)

  • [Journal Article] Metal-free oxidative cross-coupling of pyrroles with electron-rich arenes using recyclable hypervalent iodine(III) reagent2018

    • Author(s)
      K. Morimoto, T Kamitanaka, T. Dohi, Y. Kita
    • Journal Title

      Heterocycles

      Volume: 印刷中

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Efficient coupling reaction of quinone monoacetal with phenols leading to phenol biaryls2016

    • Author(s)
      T. Kamitanaka, K. Morimoto, K. Tsuboshima, D. Koseki, H. Takamuro, T. Dohi, Y. Kita
    • Journal Title

      Angew. Chem., Int. Ed.

      Volume: 55 Issue: 50 Pages: 15535-15538

    • DOI

      10.1002/anie.201608013

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] キノンモノアセタールを用いるフェノールクロスカップリング体合成とその応用2018

    • Author(s)
      上田中 徹、坪島昂平、森本功治、土肥寿文、北 泰行
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] キノンモノアセタールを利用した効率的なフェノールクロスカップリング体合成2017

    • Author(s)
      上田中 徹、森本功治、坪島昂平、土肥寿文、北 泰行
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台国際センター(宮城県、仙台市)
    • Year and Date
      2017-03-25
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthetic Strategy of Fused Benzofurans by using Quinone Monoacetals2017

    • Author(s)
      Tohru Kamitanaka, Kohei Tsuboshima, Koji Morimoto, Toshifumi Dohi, Yasuyuki Kita
    • Organizer
      26th International Society of Heterocyclic Chemistry Congress
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] キノンモノアセタールとフェノール類のクロスカップリングを応用した縮環ベンゾフラン合成2017

    • Author(s)
      上田中 徹、坪島昂平、森本功治、土肥寿文、北 泰行
    • Organizer
      第47回複素環化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] キノンモノアセタールの酸触媒制御による選択的置換型カップリング反応2016

    • Author(s)
      土肥寿文、藤田ゆり子、高室ひと穂、上田中 徹、北 泰行
    • Organizer
      第66回日本薬学会近畿支部総会・大会
    • Place of Presentation
      大阪薬科大学(大阪府、高槻市)
    • Year and Date
      2016-10-15
    • Related Report
      2016 Annual Research Report
  • [Presentation] キノンモノアセタールを用いたフェノール類のo,p-クロスカップリング体合成法2016

    • Author(s)
      上田中 徹、森本功治、坪島昂平、土肥寿文、北 泰行
    • Organizer
      第66回日本薬学会近畿支部総会・大会
    • Place of Presentation
      大阪薬科大学(大阪府、高槻市)
    • Year and Date
      2016-10-15
    • Related Report
      2016 Annual Research Report

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Published: 2016-09-02   Modified: 2019-03-29  

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