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Development of the para-selective functionalization of benzene derivatives

Research Project

Project/Area Number 16K05771
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionNagoya University

Principal Investigator

Segawa Yasutomo  名古屋大学, 理学研究科, 特任准教授 (60570794)

Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2017: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2016: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsホウ素化反応 / 選択的官能基化 / ベンゼン環パラ位 / C-Hホウ素化 / ベンゼン環 / パラ位 / ベンゼン / C-H官能基化 / ホウ素化
Outline of Final Research Achievements

It is known that the boryl group can be converted into various functional groups. If para-selective C-H bond direct borylation is possible, various functionalization of the para-positions of the benzene rings can be realized. The Iridium-catalyzed C-H borylation reaction proceeds at the meta- and para-positions of monosubstituted benzenes, and regioselectivity has not been controlled. In this study, we developed a novel catalytic system for para-selective C-H borylation to synthesize molecules with various functions and properties. In addition, this reaction was used to construct libraries for functional organic molecules and complex natural organic compounds via borylation at the late-stage of synthesis.

Academic Significance and Societal Importance of the Research Achievements

本研究では、新しい有機合成反応を開発し、それをもとに有用な分子の迅速な合成を可能にした。これは、LEDや太陽電池に代表される電子デバイスの部品となる機能性有機分子や、医薬品の候補となる生理活性分子として有用な分子を見つけるプロセスを大幅に簡略化するだけでなく、これまで手にすることのできなかった種類の有機分子を合成できるようになった。実際にバイオイメージングに応用したように、本研究によって新たに得られた有機分子は今後さまざまな場面で活用されると期待される。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (54 results)

All 2019 2018 2017 2016 Other

All Int'l Joint Research (2 results) Journal Article (14 results) (of which Int'l Joint Research: 6 results,  Peer Reviewed: 12 results,  Open Access: 3 results,  Acknowledgement Compliant: 1 results) Presentation (38 results) (of which Int'l Joint Research: 11 results,  Invited: 5 results)

  • [Int'l Joint Research] ボストン・カレッジ(米国)

    • Related Report
      2017 Research-status Report
  • [Int'l Joint Research] エモリー大学(米国)

    • Related Report
      2016 Research-status Report
  • [Journal Article] Polycyclic Arene Synthesis by Annulative pi-Extension2019

    • Author(s)
      Hideto Ito, Yasutomo Segawa, Kei Murakami, and Kenichiro Itami
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 141 Issue: 1 Pages: 3-10

    • DOI

      10.1021/jacs.8b09232

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Structural Features of Thiophene-fused Analogues of Warped Nanographene and Quintuple Helicene2019

    • Author(s)
      Hsing-An Lin, Kenta Kato, Yasutomo Segawa, Lawrence T. Scott, and Kenichiro Itami
    • Journal Title

      Chem. Sci.

      Volume: 10 Issue: 8 Pages: 2326-2330

    • DOI

      10.1039/c8sc04470h

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Synthesis and Size-Dependent Properties of [12], [16], and [24]Carbon Nanobelts2018

    • Author(s)
      Guillaume Povie, Yasutomo Segawa, Taishi Nishihara, Yuhei Miyauchi, and Kenichiro Itami
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 140 Issue: 31 Pages: 10054-10059

    • DOI

      10.1021/jacs.8b06842

    • NAID

      120006545941

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Symmetric Multiple Carbohelicenes2018

    • Author(s)
      Kenta Kato, Yasutomo Segawa, and Kenichiro Itami
    • Journal Title

      Synlett

      Volume: 30 Issue: 04 Pages: 370-377

    • DOI

      10.1055/s-0037-1610283

    • NAID

      120006545942

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] A Quintuple [6]Helicene with a Corannulene Core as a C5-symmetric Propeller-shaped マ?System2018

    • Author(s)
      Kenta Kato, Yasutomo Segawa, Lawrence T. Scott, and Kenichiro Itami
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 57 Issue: 5 Pages: 1337-1341

    • DOI

      10.1002/anie.201711985

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] A Water-soluble Warped Nanographene: Synthesis and Applications for Photo-induced Cell Death2018

    • Author(s)
      Hsing-An Lin, Yoshikatsu Sato, Yasutomo Segawa, Taishi Nishihara, Nagisa Sugimoto, Lawrence T. Scott, Tetsuya Higashiyama, and Kenichiro Itami
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 57 Issue: 11 Pages: 2874-2878

    • DOI

      10.1002/anie.201713387

    • NAID

      120006473539

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Synthesis and Structure of a Propeller-shaped Polycyclic Aromatic Hydrocarbon Containing Seven-Membered Rings2018

    • Author(s)
      Kazuya Kawai, Kenta Kato, Lingqing Peng, Yasutomo Segawa, Lawrence T. Scott, Kenichiro Itami
    • Journal Title

      Org Lett.

      Volume: 20 Issue: 7 Pages: 1932-1935

    • DOI

      10.1021/acs.orglett.8b00477

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis of a Carbon Nanobelt2017

    • Author(s)
      Guillaume Povie, Yasutomo Segawa, Taishi Nishihara, Yuhei Miyauchi, Kenichiro Itami
    • Journal Title

      Science

      Volume: 356 Issue: 6334 Pages: 172-175

    • DOI

      10.1126/science.aam8158

    • NAID

      120006318708

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Properties, and Crystal Structures of pi-Extended Double [6]Helicenes: Contorted Multi-Dimensional Stacking Lattice2017

    • Author(s)
      Takao Fujikawa, Nobuhiko Mitoma, Atsushi Wakamiya, Akinori Saeki, Yasutomo Segawa, and Kenichiro Itami
    • Journal Title

      Org. Biomol. Chem.

      Volume: 15 Issue: 21 Pages: 4697-4703

    • DOI

      10.1039/c7ob00987a

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Laterally pi-Extended Dithia[6]helicenes with Heptagons: Saddle-Helix Hybrid Molecules2017

    • Author(s)
      Takao Fujikawa, Yasutomo Segawa, and Kenichiro Itami
    • Journal Title

      J. Org. Chem.

      Volume: 82 Issue: 15 Pages: 7745-7749

    • DOI

      10.1021/acs.joc.7b01540

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Hole-transporting materials based on thiophene-fused arenes from sulfur-mediated thienannulations2017

    • Author(s)
      Lin Hsing-An, Nobuhiko Mitoma, Meng Lingkui, Yasutomo Segawa, Atsushi Wakamiya, and Kenichiro Itami
    • Journal Title

      Mater. Chem. Front.

      Volume: 2 Issue: 2 Pages: 275-280

    • DOI

      10.1039/c7qm00473g

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] カーボンナノベルトの合成2017

    • Author(s)
      瀬川泰知・伊丹健一郎
    • Journal Title

      現代化学

      Volume: 7 Pages: 36-39

    • NAID

      40021219716

    • Related Report
      2017 Research-status Report
  • [Journal Article] カーボンナノベルト合成までの軌跡 12年の歴史とドラマ2017

    • Author(s)
      伊丹健一郎・瀬川泰知・大町遼・八木亜樹子
    • Journal Title

      化学

      Volume: 72 Pages: 29-37

    • Related Report
      2017 Research-status Report
  • [Journal Article] Flexible Reaction Pocket on Bulky Diphosphine-Ir Complex Controls Regioselectivity in para-Selective C-H Borylation of Arenes2016

    • Author(s)
      Brandon E. Haines, Yutaro Saito, Yasutomo Segawa, Kenichiro Itami, Djamaladdin G. Musaev
    • Journal Title

      ACS Catalysis

      Volume: 6 Issue: 11 Pages: 7536-7546

    • DOI

      10.1021/acscatal.6b02317

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Presentation] One-dimensional Self-assembly of a Negatively Curved Aromatic Hydrocarbon2019

    • Author(s)
      KATO, Kenta; HIJIKATA, Yuh; PIRILLO, Jenny; NISHIHARA, Taishi; NAKANISHI, Yusuke; SEGAWA, Yasutomo; SCOTT, Lawrence T.; ITAMI, Kenichiro
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Ir触媒C-Hホウ素化を用いたデカアリールワープドナノグラフェンの合成2019

    • Author(s)
      加藤 健太・林 興安・瀬川 泰知・スコット ローレンス・伊丹 健一郎
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] オールベンゼンカテナンおよびトレフォイルノットの合成2019

    • Author(s)
      瀬川 泰知・桑山 元伸・土方 優・伏見 雅子・西原 大志・ピリッロ ジェニー・白崎 淳哉・久保田 夏実・伊丹 健一郎
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Synthetic Chemistry of Strained Molecular Nanocarbons2019

    • Author(s)
      瀬川泰知
    • Organizer
      JST ERATO Itami Molecular Nanocarbon Project Final Symposium
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and Properties of a Quintuple [6]Helicene with a Corannulene Core2018

    • Author(s)
      加藤健太・瀬川泰知・Scott T. Lawrence・伊丹健一郎
    • Organizer
      Enabling Excellence Japanege-European Workshop -Carbon Nanoscience and Nanotechnology-
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] One-dimentional Self-assembly of Warped Nanographene2018

    • Author(s)
      加藤健太・瀬川泰知・Lawrence T. Scott・伊丹健一郎
    • Organizer
      第50回構造有機若手の会
    • Related Report
      2018 Annual Research Report
  • [Presentation] One-dimentional Self-assembly of Warped Nanographene2018

    • Author(s)
      加藤健太・瀬川泰知・Lawrence T. Scott・伊丹健一郎
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 湾曲ナノグラフェンの一次元自己集積化2018

    • Author(s)
      加藤健太・瀬川泰知・Lawrence T. Scott・伊丹健一郎
    • Organizer
      第67回高分子討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] One-dimentional Self-assembly of Warped Nanographene2018

    • Author(s)
      加藤健太・瀬川泰知・Lawrence T. Scott・伊丹健一郎
    • Organizer
      第5回π造形科学若手研究会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Synthesis and Structure of a Propeller-Shaped Polycyclic Aromatic Hydrocarbon Containing Seven-Membered Rings2018

    • Author(s)
      川井 一矢・加藤 健太・Lingqing Peng・瀬川 泰知・Lawrence T. Scott・伊丹 健一郎
    • Organizer
      第5回π造形科学若手研究会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 湾曲ナノグラフェンの一次元自己集積化2018

    • Author(s)
      加藤健太・瀬川泰知・Lawrence T. Scott・伊丹健一郎
    • Organizer
      ITbM/IGER Chemistry Workshop
    • Related Report
      2018 Annual Research Report
  • [Presentation] シクロパラフェニレンカテナンの合成2018

    • Author(s)
      瀬川泰知・桑山元伸・伏見雅子・西原大志・伊丹健一郎
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] Synthesis and Properties of a Quintuple [6]Helicene with a Corannulene Core2018

    • Author(s)
      加藤健太・瀬川泰知・Scott T. Lawrence・伊丹健一郎
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] Synthesis and stractures of a corannulene-cored quintuple [6]helicene2018

    • Author(s)
      加藤健太・瀬川泰知・Lawrence T. Scott・伊丹健一郎
    • Organizer
      IGER Annual Meeting 2017
    • Related Report
      2017 Research-status Report
  • [Presentation] Aromatic C_H Borylation Controlled by Remote Steric Effect2018

    • Author(s)
      齋藤雄太朗・瀬川泰知・伊丹健一郎
    • Organizer
      IGER Annual Meeting 2017
    • Related Report
      2017 Research-status Report
  • [Presentation] 予期しなかった芳香環C-H官能基化反応の発見と展開2017

    • Author(s)
      瀬川泰知
    • Organizer
      東京大学大学院工学系研究科化学生命工学専攻セミナー
    • Place of Presentation
      東京大学
    • Year and Date
      2017-01-30
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] Para-Selective C-H Functionalization of Benzene Derivatives2017

    • Author(s)
      齋藤雄太朗、瀬川泰知、伊丹健一郎
    • Organizer
      グリーン自然科学国際教育研究プログラム IGER 2016年度年次報告会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2017-01-13
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] 湾曲した芳香族炭化水素の合成化学2017

    • Author(s)
      瀬川泰知
    • Organizer
      第八回南方研若手研究者セミナー
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] カーボンナノベルトの合成2017

    • Author(s)
      瀬川泰知・Guillaume Povie・西原大志・宮内雄平・伊丹健一郎
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] カーボンナノベルトの合成と構造2017

    • Author(s)
      瀬川泰知
    • Organizer
      π造形科学 第4回公開シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] カーボンナノベルトができるまで2017

    • Author(s)
      瀬川泰知
    • Organizer
      第4回π造形科学若手研究会
    • Related Report
      2017 Research-status Report
  • [Presentation] 高度に湾曲したプロペラ型π共役炭化水素の合成と構造2017

    • Author(s)
      川井一矢・瀬川泰知・伊丹健一郎
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] コラニュレンを中心にもつ5重ヘリセンの合成と構造2017

    • Author(s)
      加藤健太・瀬川泰知・伊丹健一郎
    • Organizer
      第7回CSJ化学フェスタ2017
    • Related Report
      2017 Research-status Report
  • [Presentation] コラニュレンを基盤とする新奇湾曲芳香族炭化水素の合成と構造2017

    • Author(s)
      加藤健太・瀬川泰知・Lawrence T. Scott・伊丹健一郎
    • Organizer
      π造形科学 第4回公開シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] 高度に湾曲したプロペラ型π共役炭化水素の合成と構造2017

    • Author(s)
      川井一矢・瀬川泰知・伊丹健一郎
    • Organizer
      第4回π造形科学若手研究会
    • Related Report
      2017 Research-status Report
  • [Presentation] コラニュレンを基盤とする新奇湾曲多環芳香族炭化水素の合成と構造2017

    • Author(s)
      加藤健太・瀬川泰知・伊丹健一郎
    • Organizer
      第4回π造形科学若手研究会
    • Related Report
      2017 Research-status Report
  • [Presentation] Synthesis of a Carbon Nanobelt2017

    • Author(s)
      瀬川泰知
    • Organizer
      International Symposium on Pure & Applied Chemistry (ISPAC) 2017
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis of a Carbon Nanobelt2017

    • Author(s)
      瀬川泰知
    • Organizer
      17th International Symposium on Novel Aromatic Compounds (ISNA2017)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemical Synthesis of Molecular Nanocarbons2017

    • Author(s)
      瀬川泰知
    • Organizer
      International ERATO Itami Molecular Nanocarbon Symposium 2017 "The Power of Carbon-based Materials"
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis and structures of a corannulene-cored quintuple [6]helicene2017

    • Author(s)
      加藤健太・瀬川泰知・Lawrence T. Scott・伊丹健一郎
    • Organizer
      17th International Symposium on Novel Aromatic Compounds (ISNA2017)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Structure of Corannulene-Based Quintuple [6]helicene2017

    • Author(s)
      加藤健太・瀬川泰知・Lawrence T. Scott・伊丹健一郎
    • Organizer
      International ERATO Itami Molecular Nanocarbon Symposium 2017 "The Power of Carbon-based Materials"
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Structure of a Highly Warped Propeller-Shaped π-Conjugated Hydrocarbon2017

    • Author(s)
      川井一矢・瀬川泰知・伊丹健一郎
    • Organizer
      International ERATO Itami Molecular Nanocarbon Symposium 2017 "The Power of Carbon-based Materials"
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] C_H Borylation of Benzene Derivatives with Remote Steric Control2017

    • Author(s)
      齋藤雄太朗・瀬川泰知・伊丹健一郎
    • Organizer
      International ERATO Itami Molecular Nanocarbon Symposium 2017 "The Power of Carbon-based Materials"
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] 遠隔立体制御による芳香環の位置選択的C_Hホウ素化反応の開発と応用2017

    • Author(s)
      齋藤雄太朗・瀬川泰知・伊丹健一郎
    • Organizer
      第35回メディシナルケミストリーシンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] 遠隔立体制御による芳香環の位置選択的C_Hホウ素化反応の開発と応用2017

    • Author(s)
      齋藤雄太朗・瀬川泰知・伊丹健一郎
    • Organizer
      第7回CSJ化学フェスタ2017
    • Related Report
      2017 Research-status Report
  • [Presentation] 遠隔立体制御によるベンゼン誘導体のC_Hホウ素化反応2017

    • Author(s)
      齋藤雄太朗・瀬川泰知・伊丹健一郎
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] ベンゼン誘導体のパラ位選択的官能基化法の開発2016

    • Author(s)
      齋藤雄太朗、瀬川泰知、伊丹健一郎
    • Organizer
      第34回メディシナルケミストリーシンポジウム
    • Place of Presentation
      つくば国際会議場
    • Year and Date
      2016-12-01
    • Related Report
      2016 Research-status Report
  • [Presentation] Para-Selective C-H Functionalization of Benzene Derivatives2016

    • Author(s)
      齋藤雄太朗、瀬川泰知、伊丹健一郎
    • Organizer
      2016 International C-H Functionalization Workshop
    • Place of Presentation
      名古屋大学
    • Year and Date
      2016-06-16
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research

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Published: 2016-04-21   Modified: 2022-02-21  

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