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Novel synthesis of biaryls via metal-free cross-coupling reaction and its application

Research Project

Project/Area Number 23790030
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionRitsumeikan University

Principal Investigator

MORIMOTO Koji  立命館大学, 立命館グローバル・イノベー ション研究機構, ポストドクトラルフェロ (10543952)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2012: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2011: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords有機合成化学 / 芳香族 / 超原子価ヨウ素 / 機能性有用化合物 / クロスカップリング / ビアリール類 / 機能性材料 / 酸化的カップリング / ビアリール / チオフェン類 / 芳香族化合物
Research Abstract

Biaryl compounds are versatile building blocks in the synthesis of natural products, pharmaceuticals, agricultural chemicals and π-conjugated organic materials. Therefore, the development of convenient cross-coupling reaction for giving biaryls is one of the important subjects in organic chemistry.Recently, we have developed a new synthetic method that enables metal-free regioselective oxidative coupling of 3-substituted thiphenes using hypervalent iodine(III) reagents. I have applied our coupling reaction of thiphenes to the synthesis of thiophene organic dyes as MK-2. Futher study for the oxidative coupling reaction, we also developed a metal-free direct synthesis of the discotic liquid crystal hexahydroxytriphenylene (HHTP) using hypervalent iodine reagent.

Report

(3 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Research-status Report
  • Research Products

    (40 results)

All 2013 2012 2011 Other

All Journal Article (10 results) (of which Peer Reviewed: 10 results) Presentation (27 results) Book (1 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Oxidative Trimerization of Catechol to Hexahydroxytriphenylene2013

    • Author(s)
      Morimoto, Koji; Dohi, Toshifumi;Kita, Yasuyuki,
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2013 Issue: 9 Pages: 1659-1662

    • DOI

      10.1002/ejoc.201201515

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Efficient Synthesis of Regioregular Oligothiophene Photovaltaic Dye Molecules, MK-2 and Related Compounds : A Cooperative Hypervalent Iodine and Metal Catalyzed Synthetic Route2013

    • Author(s)
      Nobutaka Yamaoka, Yasuyuki Kita, et al.
    • Journal Title

      Chemistry A European Journal

      Volume: 19 Issue: 6 Pages: 2067-2075

    • DOI

      10.1002/chem.201203503

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Boron-Substituted Diaryliodonium Salts and Selective Transformation into Functionalized ArylBoronates2012

    • Author(s)
      T. Dohi, Y. Kita et al.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 51 Issue: 50 Pages: 12555-12558

    • DOI

      10.1002/anie.201206917

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] An excellent dual recycling strategy for the hypervalent iodine/nitrosyl radical mediated selective oxidation of alcohols to aldehydeds and ketones2012

    • Author(s)
      T. Dohi, Y. Kita et al.
    • Journal Title

      Green Chem.

      Volume: 14 Issue: 5 Pages: 1493-1501

    • DOI

      10.1039/c2gc16632a

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hypervalent iodine induced metal-free C-H cross couplings to biaryls2011

    • Author(s)
      Kita, Yasuyuki; Dohi, Toshifumi; Morimoto, Koji
    • Journal Title

      Yuki Gosei Kagaku Kyokaishi

      Volume: 69 Pages: 1241-1250

    • NAID

      10029927823

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Metal-free C-H cross-coupling toward oxygenated naphthalene-benzene linked biaryls2011

    • Author(s)
      Dohi T., Ito M., Itani I., Yamaoka N., Morimoto K., Fujioka H., Kita Y.
    • Journal Title

      Organic Letters

      Volume: 13 Pages: 6208-6211

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Metal-free oxidative coupling reactions via iodonium intermediates: The efficient synthesis of bithiophenes using hypervalent iodine reagents2011

    • Author(s)
      Morimoto K., Nakae T., Yamaoka N., Dohi T., Kita Y.
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 31 Pages: 6326-6334

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Hypervalent iodine induced metal-free C-H cross couplings to biaryls2011

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

      Yuki Gosei Kagaku Kyokaishi

      Volume: 69 Pages: 1241-1250

    • NAID

      10029927823

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Metal-free direct biaryl coupling reaction of heteroaromatic compounds via iodonium intermediate2011

    • Author(s)
      Morimoto K.
    • Journal Title

      Yakugaku Zasshi

      Volume: 131 Pages: 1339-1345

    • NAID

      130001871941

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] The synthetic and biological studies of discorhabdins and related compounds2011

    • Author(s)
      Wada Y., Harayama Y., Kamimura D., Yoshida M., Shibata T., Fujiwara K., Morimoto K., Fujioka H., Kita Y.
    • Journal Title

      Organic and Biomolecular Chemistry

      Volume: 9 Pages: 4959-4976

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] 効率的なフェノール類の酸化的クロスカップリング反応の開発2013

    • Author(s)
      森本功治,坂本一真,大西佑亮,土肥寿文,北泰行
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      パシフィコ横浜(神奈川県)
    • Year and Date
      2013-03-30
    • Related Report
      2012 Final Research Report
  • [Presentation] 超原子価ヨウ素カップリングを利用するチオフェン系有機色素の効率的合成2013

    • Author(s)
      土肥寿文,山岡信貴,住田康平, 中村彰太,森本功治,北 泰行
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      パシフィコ横浜(神奈川県)
    • Year and Date
      2013-03-29
    • Related Report
      2012 Final Research Report
  • [Presentation] 効率的なフェノール類の酸化的クロスカップリング反応の開発2013

    • Author(s)
      森本功治、坂本-真、大西佑亮、土肥寿文、北 泰行
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      パシフィコ横浜 (神奈川県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 超原子価ヨウ素カップリングを利用するチオフェン系有機色素の効率的合成2013

    • Author(s)
      土肥寿文、山岡信貴、住田康平、中村彰太、森本功治、北 泰行
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      パシフィコ横浜 (神奈川県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 天然物 Lactonamycin を志向した芳香族酸化型スピロラクトン骨格構築法2012

    • Author(s)
      森本功治、仲江朋史、宮本健 志、畑佳世子、Simon B. Cammerer、土肥寿 文、北泰行
    • Organizer
      第102回有機合成シンポジウム
    • Place of Presentation
      早稲田国際会議場(東京都)
    • Year and Date
      2012-11-09
    • Related Report
      2012 Final Research Report
  • [Presentation] 含窒素ヘテロ芳香族ヨードニウム化合物のカップリング反応研究2012

    • Author(s)
      森本功治、大西佑亮、山岡信 貴、土肥寿文、北 泰行
    • Organizer
      第62回日本薬学会近畿支部総会・大会
    • Place of Presentation
      武庫川女子大学(兵庫県)
    • Year and Date
      2012-10-20
    • Related Report
      2012 Final Research Report
  • [Presentation] ヨウ素反応剤を用いるフェノール類と芳香族化合物とのク ロスカップリング2012

    • Author(s)
      森本功治、坂本一真、井谷 樹、土肥寿文、北 泰行
    • Organizer
      第62回 日本薬学会近畿支部総会・大会
    • Place of Presentation
      武庫川女子大学(兵庫県)
    • Year and Date
      2012-10-20
    • Related Report
      2012 Final Research Report
  • [Presentation] Metal-Free Oxidative Coupling Reaction: The Efficient Synthesis of Bithiophenes Using Hypervalent Iodine Reagent2012

    • Author(s)
      Morimoto Koji
    • Organizer
      International Conference 'Catalysis in Organic Synthesis'
    • Place of Presentation
      Moscow, Rosia
    • Year and Date
      2012-09-17
    • Related Report
      2012 Final Research Report
  • [Presentation] The Synthetic and Biological Studies of Discorhabdin Analogues2012

    • Author(s)
      Morimoto Koji
    • Organizer
      9th International Conference on Organic Synthesis
    • Place of Presentation
      Melbourne,Australia
    • Year and Date
      2012-07-03
    • Related Report
      2012 Final Research Report
  • [Presentation] 置換チオフェン類の効率的酸化的カップリング 反応2012

    • Author(s)
      森本 功治,山岡 信貴,仲江 朋史,土肥 寿文,北 泰行
    • Organizer
      日本薬学会 132 年会
    • Place of Presentation
      北海道大学(北海道)
    • Year and Date
      2012-03-30
    • Related Report
      2012 Final Research Report
  • [Presentation] 効率的なフェノール類の酸化的脱芳香化を伴う官能基化反応2012

    • Author(s)
      森本功治,仲江朋史,畑佳 世子,B. Cammerer SIMON,土肥寿文,北 泰行
    • Organizer
      日本薬学会132年会
    • Place of Presentation
      北海道大学(北海道)
    • Year and Date
      2012-03-29
    • Related Report
      2012 Final Research Report
  • [Presentation] Metal-Free Oxidative Coupling Reaction: The Efficient Synthesis of Bithiophenes Using Hypervalent Iodine Reagent2012

    • Author(s)
      Koji Morimoto
    • Organizer
      International Conference 'Catalysis in Organic Synthesis',
    • Place of Presentation
      Moscow (Russia)
    • Related Report
      2012 Annual Research Report
  • [Presentation] The Synthetic and Biological Studies of Discorhabdin Analogues2012

    • Author(s)
      Koji Morimoto
    • Organizer
      9th International Conference on Organic Synthesis
    • Place of Presentation
      Melbourne (Australia)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 置換チオフェン類の効率的酸化的カップリング反応2012

    • Author(s)
      ◯森本 功治,山岡 信貴,仲江 朋史,土肥 寿文,北 泰行
    • Organizer
      日本薬学会132年会
    • Place of Presentation
      北海道大学(北海道)
    • Related Report
      2011 Research-status Report
  • [Presentation] 効率的なフェノール類の酸化的脱芳香化を伴う官能基化反応2012

    • Author(s)
      森本 功治,◯仲江 朋史,畑 佳世子,B. Cammerer SIMON,土肥 寿文,北 泰行
    • Organizer
      日本薬学会132年会
    • Place of Presentation
      北海道大学(北海道)
    • Related Report
      2011 Research-status Report
  • [Presentation] TheSynthetic and Biological Studies ofDiscorhabdin Analogues2011

    • Author(s)
      Morimoto Koji
    • Organizer
      8th AFMC International Medicinal Chemistry Symposium (AIMECS)
    • Place of Presentation
      京王プラザ ホテル(東京都)
    • Year and Date
      2011-12-01
    • Related Report
      2012 Final Research Report
  • [Presentation] ヘテ ロ芳香族化合物の位置選択的な酸化的カップリング反応2011

    • Author(s)
      森本功治・山岡信貴・仲江 朋文・土肥寿文・北 泰行
    • Organizer
      第14回 ヨウ素学会シンポジウム
    • Place of Presentation
      千葉大学けやき会館(千葉県)
    • Year and Date
      2011-11-18
    • Related Report
      2012 Final Research Report
  • [Presentation] 遷移金属触媒を用いないヘテロ芳香族化合物のクロスカップリング反応の開発2011

    • Author(s)
      森本功治
    • Organizer
      第61回 日本薬学会近畿支部総会・大会
    • Place of Presentation
      神戸学院大学ポートアイランドキャンパス(兵庫県)
    • Year and Date
      2011-10-22
    • Related Report
      2012 Final Research Report
  • [Presentation] 超原子価ヨウ素反応剤を用いた効率的スピロラクトン形成反応の開発と天然物合成への応用2011

    • Author(s)
      森本 功治、仲江 朋史、畑 佳 世子、Simon B. Cammerer、土肥 寿文、北泰行
    • Organizer
      第41回複素環化学討論会
    • Place of Presentation
      熊本市民会館(崇城大学市民ホール)(熊本県)
    • Year and Date
      2011-10-20
    • Related Report
      2012 Final Research Report
  • [Presentation] Metal-Free Oxidative Biaryl Coupling via the Iodonium(III)-Intermediate2011

    • Author(s)
      Morimoto Koji
    • Organizer
      The 23rd International Congress on Heterocyclic Chemistry (ICHC-23)
    • Place of Presentation
      Glasgow, UK
    • Year and Date
      2011-08-02
    • Related Report
      2012 Final Research Report
  • [Presentation] KitaThe Synthetic and Biological Studies of Discorhabdin Analogues2011

    • Author(s)
      Yasufumi Wada, ○Koji Morimoto, Hiromichi Fujioka, and Yasuyuki
    • Organizer
      8th AFMC International Medicinal Chemistry Symposium (AIMECS)
    • Place of Presentation
      KEIO PLAZA HOTEL TOKYO(東京都)
    • Related Report
      2011 Research-status Report
  • [Presentation] ヘテロ芳香族化合物の位置選択的な酸化的カップリング反応2011

    • Author(s)
      ○森本功治・山岡信貴・仲江朋史・土肥寿文・北 泰行
    • Organizer
      第14回 ヨウ素学会シンポジウム
    • Place of Presentation
      千葉大学 けやき会館(千葉県)
    • Related Report
      2011 Research-status Report
  • [Presentation] 遷移金属触媒を用いないヘテロ芳香族化合物のクロスカップリング反応の開発2011

    • Author(s)
      ○森本功治
    • Organizer
      第61 回 日本薬学会近畿支部総会・大会
    • Place of Presentation
      神戸学院大学(兵庫県)
    • Related Report
      2011 Research-status Report
  • [Presentation] 超原子価ヨウ素反応剤を用いた効率的スピロラクトン化反応の開発と天然物への応用2011

    • Author(s)
      森本功治,○仲江朋史,畑佳世子,Simon B. Cammerer,土肥寿文,北 泰行
    • Organizer
      第41回複素環化学討論会
    • Place of Presentation
      崇城大学市民ホール(熊本県)
    • Related Report
      2011 Research-status Report
  • [Presentation] KitaMetal-Free Oxidative Biaryl Coupling via the Iodonium(III)-Intermediate2011

    • Author(s)
      ○Koji Morimoto, Nobutaka Yamaoka, Tomofumi Nakae, Toshifumi Dohi and Yasuyuki
    • Organizer
      The 23rd International Congress on Heterocyclic Chemistry (ICHC-23)
    • Place of Presentation
      Scottish Exhibition and Conference Centre Glasgow, UK(スコットランド)
    • Related Report
      2011 Research-status Report
  • [Presentation] ヨウ素反応剤を用いるフェノール類と芳香族化合物とのクロスカップリング

    • Author(s)
      森本功治、坂本一真、井谷 樹、土肥寿文、北 泰行
    • Organizer
      第62回 日本薬学会近畿支部総会・大会
    • Place of Presentation
      武庫川女子大学薬学部 (兵庫県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 含窒素ヘテロ芳香族ヨードニウム化合物のカップリング反応研究

    • Author(s)
      森本功治、大西佑亮、山岡信貴、土肥寿文、北 泰行
    • Organizer
      第62回 日本薬学会近畿支部総会・大会
    • Place of Presentation
      武庫川女子大学薬学部 (兵庫県)
    • Related Report
      2012 Annual Research Report
  • [Book] 化学 66 巻 Non-レアメタルなクロスカップリング反応2011

    • Author(s)
      北 泰行・土肥寿文・森本功治
    • Publisher
      化学同人
    • Related Report
      2012 Final Research Report
  • [Patent(Industrial Property Rights)] 2,3,6,7,10,11-ヘキサヒドロキシト リフェニレン類の製造方法2012

    • Inventor(s)
      北 泰行,土肥寿文、森本功治
    • Industrial Property Rights Holder
      学校法人 立命館
    • Filing Date
      2012-08-06
    • Related Report
      2012 Final Research Report
  • [Patent(Industrial Property Rights)] 2,3,6,7,10,11-ヘキサヒドロキシト リフェニレン類の製造方法2012

    • Inventor(s)
      北 泰行,土肥寿文、森本功治
    • Industrial Property Rights Holder
      学校法人 立命館
    • Filing Date
      2012-08-06
    • Related Report
      2012 Final Research Report

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Published: 2011-08-05   Modified: 2019-07-29  

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