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Development of Practical Synthetic Methods for Substituted Aromatic Compounds

Research Project

Project/Area Number 20750069
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionChiba University

Principal Investigator

YOSHIDA Kazuhiro  Chiba University, 大学院・理学研究科, 准教授 (60375607)

Project Period (FY) 2008 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2009: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2008: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywordsメタセシス / 閉環 / グラブス触媒 / 芳香族化合物 / オレフィンメタセシス / ベンゼン / フェノール / スチレン
Research Abstract

The demand for functionalized aromatic compounds is growing rapidly in many research fields. Therefore, the efficient synthesis of desired aromatic compounds is a critical issue in organic synthesis. In this study, we developed new synthetic approaches to versatile aromatic compounds, such as phenols, benzenes, 3-hydroxypyridines, and styrenes, by ring-closing olefin metathesis (RCM)/aromatization and ring-closing enyne metathesis (RCEM)/aromatization of acyclic precursors. The advantages in terms of simplicity, flexibility, and avoidance of the formation of regioisomers are proof of the versatility of this method for the synthesis of aromatic compounds.

Report

(3 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • Research Products

    (30 results)

All 2010 2009 2008 Other

All Journal Article (14 results) (of which Peer Reviewed: 14 results) Presentation (9 results) Remarks (3 results) Patent(Industrial Property Rights) (4 results)

  • [Journal Article] Synthesis of Substituted Aromatic Compounds Using Ruthenium-Catalyzed Ring-Closing Metathesis2009

    • Author(s)
      Kazuhiro Yoshida, Tsuneo Imamoto, Akira Yanagisawa
    • Journal Title

      J. Synth. Org. Chem., Jpn. 67

      Pages: 876-888

    • NAID

      10025399994

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Carbocyclic Aromatic Compounds Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis2009

    • Author(s)
      Hidetoshi Takahashi, Kazuhiro Yoshida, Akira Yanagisawa
    • Journal Title

      J. Org. Chem. 74

      Pages: 3632-3640

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 3-Hydroxypyridines Using Ruthenium-Catalyzed Ring-Closing Olefin Metathesis2009

    • Author(s)
      Kazuhiro Yoshida, Fumihiro Kawagoe, Kazushi Hayashi, Shingo Horiuchi, Tsuneo Imamoto, Akira Yanagisawa
    • Journal Title

      Org. Lett. 11

      Pages: 515-518

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 3-Hydroxypyridines Using Ruthenium-Catalyzed Ring-Closing Olefin Metathesis2009

    • Author(s)
      Kazuhiro Yoshida
    • Journal Title

      Organic Letters 11

      Pages: 515-518

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 3-Hydroxypyridines Using Ruthenium-Catalyzed Ring-Closing Olefin Metathesis2009

    • Author(s)
      Kazuhiro Yoshida
    • Journal Title

      J.Org.Chem. 74

      Pages: 3632-3640

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Substituted Aromatic Compounds Using Ruthenium-Catalyzed Ring-Closing Metathesis2009

    • Author(s)
      Kazuhiro Yoshida
    • Journal Title

      J.Synth.Org.Chem., Jpn. 67

      Pages: 876-888

    • NAID

      10025399994

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Substituted Phenols by Using the Ring-Closing Metathesis/Isoaromatization Approach2008

    • Author(s)
      Kazuhiro Yoshida, Rintaro Narui, Tsuneo Imamoto
    • Journal Title

      Chem. Eur. J. 14

      Pages: 9706-9713

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Styrenes Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis2008

    • Author(s)
      Kazuhiro Yoshida, Yuka Shishikura, Hidetoshi Takahashi, Tsuneo Imamoto
    • Journal Title

      Org. Lett. 10

      Pages: 2777-2780

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Substituted Benzenes and Phenols via Ring-Closing Olefin Metathesis2008

    • Author(s)
      Kazuhiro Yoshida, Hidetoshi Takahashi, Tsuneo Imamoto
    • Journal Title

      Chem. Eur. J. 14

      Pages: 8246-8261

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Aromatic Compounds Using Combinations of Ring-Closing Olefin Metathesis, Dehydration, Oxidation, and Tautomerization2008

    • Author(s)
      Kazuhiro Yoshida, Takeharu Toyoshima, Tsuneo Imamoto
    • Journal Title

      Bull. Chem. Soc. Jpn. 81

      Pages: 1512-1517

    • NAID

      10024446816

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Substituted Phenols by Using the Ring-Closing Metathesis/ Isoaromatization Approach2008

    • Author(s)
      Kazuhiro Yoshida
    • Journal Title

      Chemistry-A European Journal 14

      Pages: 9706-9713

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Styrenes Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis2008

    • Author(s)
      Kazuhiro Yoshida
    • Journal Title

      Organic Letters 10

      Pages: 2777-2780

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Substituted Benzenes and Phenols via Ring-Closing Olefin Metathesis2008

    • Author(s)
      Kazuhiro Yoshida
    • Journal Title

      Chemistry-A European Journal 14

      Pages: 8246-8261

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Aromatic Compounds Using Combinations of Ring-Closing Olefin Metathesis, Dehydration, Oxidation, and Tautomerization2008

    • Author(s)
      Kazuhiro Yoshida
    • Journal Title

      Bulletin of the Chemical Society of Japan 81

      Pages: 1512-1517

    • NAID

      10024446816

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] タンデム閉環エンインメタセシス/オレフィンメタセシスを用いるビアリール化合物の合成2010

    • Author(s)
      志田寛明
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      京都
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] ルテニウム触媒閉環メタセシスを用いるインドールおよびカルバゾールの合成2010

    • Author(s)
      林和史
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      京都
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] Synthesis of Heterocyclic Aromatic Compounds Using Ruthenium-Catalyzed Ring-Closing Metathesis2009

    • Author(s)
      林和史
    • Organizer
      11th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2009-11-11
    • Related Report
      2009 Annual Research Report
  • [Presentation] 閉環エンインメタセシスを利用する芳香族化合物合成法の開発2009

    • Author(s)
      高橋英寿
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2009-03-30
    • Related Report
      2008 Annual Research Report
  • [Presentation] 閉環メタセシスを利用する芳香族化合物合成2009

    • Author(s)
      吉田和弘
    • Organizer
      平成20年度第2回有機金属若手研究者の会
    • Place of Presentation
      東京
    • Year and Date
      2009-03-26
    • Related Report
      2008 Annual Research Report
  • [Presentation] A Synthetic Approach to Aromatic Compounds Using Ring-Closing Olefin Metathesis and Ring-Closing Enyne Metathesis2008

    • Author(s)
      高橋英寿
    • Organizer
      第55回有機金属討論会
    • Place of Presentation
      大阪
    • Year and Date
      2008-09-30
    • Related Report
      2008 Annual Research Report
  • [Presentation] 閉環オレフィンメタセシスを利用する芳香族化合物の合成2008

    • Author(s)
      吉田和弘
    • Organizer
      第2回関東支部大会(有機合成化学協会関東支部)
    • Place of Presentation
      (桐生)[招待講演]
    • Year and Date
      2008-09-18
    • Related Report
      2009 Final Research Report
  • [Presentation] 閉環オレフィンメタセシスを利用する芳香族化合物の合成2008

    • Author(s)
      吉田和弘
    • Organizer
      第2回有機合成化学協会関東支部大会
    • Place of Presentation
      桐生
    • Year and Date
      2008-09-18
    • Related Report
      2008 Annual Research Report
  • [Presentation] A Synthetic Approach to Aromatic Compounds Using Ring-Closing Olefi n Metathesis and Ring-Closing Enyne Metathesis2008

    • Author(s)
      高橋英寿
    • Organizer
      17th International Conference on Organic Synthesis
    • Place of Presentation
      Daejeon, South Korea
    • Year and Date
      2008-06-26
    • Related Report
      2008 Annual Research Report
  • [Remarks]

    • URL

      http://ceres.s.chiba-u.ac.jp/

    • Related Report
      2009 Final Research Report
  • [Remarks]

    • URL

      http://ceres.s.chiba-u.ac.jp/

    • Related Report
      2009 Annual Research Report
  • [Remarks]

    • URL

      http://ceres.s:chiba-u.ac.jp/

    • Related Report
      2008 Annual Research Report
  • [Patent(Industrial Property Rights)] ビアリール化合物を製造する方法2009

    • Inventor(s)
      吉田和弘、高橋英寿、柳澤章
    • Industrial Property Rights Holder
      国立大学法人千葉大学
    • Industrial Property Number
      2009-055577
    • Filing Date
      2009-03-09
    • Related Report
      2009 Final Research Report
  • [Patent(Industrial Property Rights)] ビアリール化合物を製造する方法2009

    • Inventor(s)
      吉田和弘, 高橋英寿, 柳澤章
    • Industrial Property Rights Holder
      国立大学法人千葉大学
    • Industrial Property Number
      2009-055577
    • Filing Date
      2009-03-09
    • Related Report
      2008 Annual Research Report
  • [Patent(Industrial Property Rights)] ベンゼン誘導体の製造方法及びそれに有用なシクロヘキセン誘導体の製造方法2008

    • Inventor(s)
      吉田和弘、豊島武春、今本恒雄
    • Industrial Property Rights Holder
      国立大学法人千葉大学
    • Patent Publication Number
      2008-106004
    • Acquisition Date
      2008-05-08
    • Related Report
      2009 Final Research Report
  • [Patent(Industrial Property Rights)] ベンゼン誘導体の製造方法及びそれに有用なシクロヘキセン誘導体の製造方法2008

    • Inventor(s)
      吉田和弘, 豊島武春, 今本恒雄
    • Industrial Property Rights Holder
      国立大学法人千葉大学
    • Patent Publication Number
      2008-106004
    • Filing Date
      2008-05-08
    • Related Report
      2008 Annual Research Report

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Published: 2008-04-01   Modified: 2016-04-21  

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