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Development of complex aromatic compounds based on aryne-umpolung via Ni-complexation

Research Project

Project/Area Number 16K17907
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionInstitute of Physical and Chemical Research

Principal Investigator

Sumida Yuto  国立研究開発法人理化学研究所, ライフサイエンス技術基盤研究センター, 研究員 (40630976)

Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2017: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2016: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsアライン / アライン-ニッケル錯体 / 多置換芳香環 / 多環芳香族炭化水素 / 含ホウ素前駆体 / 非対称トリフェニレン / ベンゼン環 / 極性転換 / アライン-Ni錯体 / 多置換芳香環合成 / ベンザイン / アライン金属錯体 / ニッケル
Outline of Final Research Achievements

Aryne is an extremely reactive species and has been used as a useful building block to construct multi-substituted aromatic compounds. In this research, for developing application methods of aryne, we have established a facile preparation method of aryne-Ni complexes having various substituents. We also have achieved new methods using umpolung of aryne, that is, the synthesis of multi-substituted aromatic rings via double functionalization of aryne-Ni complexes, and cross-selective [2+2+2] cycloaddition of three kinds of arynes giving unsymmetrical triphenylenes.
By using these methods, it has become possible to make structurally complex polysubstituted arenes or polycyclic aromatic hydrocarbons which are difficult to synthesize by conventional methods. We expect that these methods enable us to obtain the straightforward construction of diverse aromatic molecules.

Report

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

    (17 results)

All 2017 2016

All Journal Article (4 results) (of which Peer Reviewed: 4 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (13 results) (of which Int'l Joint Research: 6 results,  Invited: 1 results)

  • [Journal Article] A study on an unusual SN2 mechanism in the methylation of benzyne through nickel-complexation2017

    • Author(s)
      Hatakeyama Makoto、Sakamoto Yuki、Ogata Koji、Sumida Yuto、Sumida Tomoe、Hosoya Takamitsu、Nakamura Shinichiro
    • Journal Title

      Phys. Chem. Chem. Phys.

      Volume: 19 Issue: 39 Pages: 26926-26933

    • DOI

      10.1039/c7cp04739h

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Prenatal neurogenesis induction therapy normalizes brain structure and function in Down syndrome mice2017

    • Author(s)
      Akiko Nakano-Kobayashi, Tomonari Awaya, Isao Kii, Yuto Sumida, Yukiko Okuno, Suguru Yoshida, Tomoe Sumida, Haruhisa Inoue, Takamitsu Hosoya and Masatoshi Hagiwara
    • Journal Title

      Proceedings of the National Academy of Sciences of the United States of america

      Volume: 114 Issue: 38 Pages: 10268-10273

    • DOI

      10.1073/pnas.1704143114

    • NAID

      130007900113

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Nickel-Catalyzed Reductive Cross-Coupling of Aryl Triflates and Nonaflates with Alkyl Iodides2017

    • Author(s)
      Sumida Yuto、Hosoya Takamitsu、Sumida Tomoe
    • Journal Title

      Synthesis

      Volume: 49 Issue: 16 Pages: 3590-3601

    • DOI

      10.1055/s-0036-1588464

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Preparation of Aryne-Nickel Complexes from ortho-Borylaryl Triflates2016

    • Author(s)
      Yuto. Sumida, Tomoe. Sumida, Daisuke. Hashizume, Takamitsu. Hosoya
    • Journal Title

      Organic Letters

      Volume: 18 Issue: 21 Pages: 5600-5603

    • DOI

      10.1021/acs.orglett.6b02831

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] アライン-ニッケル錯体の簡便調製法の開発とそれを利用した多彩な芳香族化合物の合成2017

    • Author(s)
      隅田有人,隅田ともえ,細谷孝充
    • Organizer
      第137回日本薬学会
    • Place of Presentation
      東北大学 仙台
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] Synthesis of Unsymmetrical Triphenylenes via Cross-Selective [2+2+2] Cycloaddition Between Aryne_Ni Complex and Two Arynes2017

    • Author(s)
      隅田有人, 隅田ともえ, 細谷孝充
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ホウ素化合物を起点とする多彩な芳香族化合物の合成法の開発2017

    • Author(s)
      隅田有人
    • Organizer
      第11回六甲有機合成研究会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Arynes and Aryne_Nickel Complexes From ortho-Borylaryl Triflates2017

    • Author(s)
      Yuto Sumida, Tomoe Sumida, Takamitsu Hosoya
    • Organizer
      IMEBORON 16
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Unsymmetrical Triphenylenes via Cross-Selective [2+2+2] Cycloaddition of Aryne_Nickel Complex with Two Arynes2017

    • Author(s)
      Tomoe Sumida, Yuto Sumida, Takamitsu Hosoya
    • Organizer
      OMCOS 19
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Nickel-Catalyzed Reductive Alkylation of Aryl and Alkenyl Sulfonates with Alkyl Iodides2017

    • Author(s)
      Yuto Sumida, Tomoe Sumida, Takamitsu Hosoya
    • Organizer
      OMCOS 19
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 共通前駆体からのアライン発生およびアライン-ニッケル錯体調製と複雑芳香環合成への応用2017

    • Author(s)
      隅田有人, 隅田ともえ, 細谷孝充
    • Organizer
      第15回次世代を担う有機化学シンポジウム講演要旨集
    • Related Report
      2017 Annual Research Report
  • [Presentation] Ir触媒による1-ヒドロシリルナフタレンのペリ位選択的C-Hホウ素化2017

    • Author(s)
      隅田有人, 原田龍, 細谷孝充
    • Organizer
      第97回日本化学会春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 神経新生促進によるダウン症モデルにおける脳発達障害の是正2017

    • Author(s)
      小林亜希子, 粟屋智就, 喜井勲, 隅田有人, 奥野友紀子, 和根崎圭子, 吉田優, 隅田ともえ, 井上治久, 細谷孝充, 萩原正敏
    • Organizer
      第90回日本生化学会大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] アライン-ニッケル錯体の簡便調製法の開発とそれを利用した多彩な芳香族化合物の合成2017

    • Author(s)
      隅田有人, 隅田ともえ, 細谷孝充
    • Organizer
      第137回日本薬学会年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Aryne-nickel complexes: a facile synthetic method and application to the synthesis of diverse aromatic compounds based on their unique reactivity2016

    • Author(s)
      Yuto SUMIDA, Tomoe SUMIDA, Takamitsu HOSOYA
    • Organizer
      International Symposium on C-O activation
    • Place of Presentation
      Himeji Chamber of Commerce and Industry Hyogo Japan
    • Year and Date
      2016-10-25
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Generation of Arynes and Preparation of Aryne-nickel Complexes From ortho-borylaryl Triflates2016

    • Author(s)
      Yuto SUMIDA, Tomoe SUMIDA, Takamitsu HOSOYA
    • Organizer
      ICOMC 2016
    • Place of Presentation
      Melbourne Australia
    • Year and Date
      2016-07-17
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Convenient Synthesis and Synthetic Applications of Aryne-Nickel Complexes2016

    • Author(s)
      Yuto SUMIDA, Tomoe SUMIDA, Takamitsu HOSOYA
    • Organizer
      ISOR-12
    • Place of Presentation
      Kyoto Terrsa Kyoto Japan
    • Year and Date
      2016-04-22
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research

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Published: 2016-04-21   Modified: 2019-03-29  

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