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Synthesis of Polyaromatics by Dehydrate Annulation of Aromatic Carboxylic Acids with Alkynes

Research Project

Project/Area Number 17K05866
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

Fukuyama Takahide  大阪府立大学, 理学(系)研究科(研究院), 准教授 (60332962)

Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2019: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2017: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords多環方向族化合物 / 芳香族カルボン酸 / アルキン / 脱水型環化反応 / 多環芳香族化合物 / 環化反応 / シクロヘプタフルオレン / シクロヘプタカルバゾール / ロジウム / 触媒反応
Outline of Final Research Achievements

In this study, synthesis of a variety of polycyclic aromatic compounds was investigated via transition metal-catalyzed dehydrate annulation of aromatic carboxylic acids with alkynes involving successive C-O/C-H bond activation. Polycyclic aromatic hydrocarbons, such as perinaphthenones and phenanthrenes, and heteroaromatic compounds, such as quinolinones and thiochromenones were successfully synthesized through rhodium catalyzed dehydrate annulation of aromatic carboxylic acids with alkynes. The reaction of fluorenone carboxylic acid with alkynes proceeded with construction of seven-menvered ring to give a tetracyclic aromatic compound, cycloheptafluorendione.

Academic Significance and Societal Importance of the Research Achievements

本研究は、容易に利用可能なカルボン酸とアルキンを基質とし、C-O/C-H結合の連続活性化に基づいた、水を副生成物とする環境調和型の多環式化合物の構築法を提案するものであり、種々の方向族カルボン酸とアルキンとの反応により、ペリナフテノンやフェナントレン、シクロヘプタフルオレンジオンなどの多環芳香族炭化水素やキノリノン、チオクロメノン等のヘテロ原子を含む多環方向族複素環の効率合成を達成した。さらなる発展的研究により、機能性材料の開発研究、生物活性物質の開発研究を加速化させ、医学・薬学・材料科学等の広範な分野に貢献することが期待される。

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • 2017 Research-status Report
  • Research Products

    (29 results)

All 2020 2019 2018 2017 Other

All Int'l Joint Research (3 results) Journal Article (13 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 13 results,  Open Access: 7 results) Presentation (13 results) (of which Int'l Joint Research: 7 results,  Invited: 6 results)

  • [Int'l Joint Research] Sorbonne University(フランス)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] 台湾交通大学(その他の国・地域)

    • Related Report
      2018 Research-status Report
  • [Int'l Joint Research] ソルボンヌ大学(フランス)

    • Related Report
      2018 Research-status Report
  • [Journal Article] Synthesis of Aliphatic Amides through a Photoredox Catalyzed Radical Carbonylation Involving Organosilicates as Alkyl Radical, Precursors2020

    • Author(s)
      A, Cartier, E. Levernier, A-L. Dhimane, T. Fukuyama, C. Ollivier, I. Ryu, L. Fensterbank
    • Journal Title

      Adv. Synth. Catal.

      Volume: - Issue: 11 Pages: 2254-2259

    • DOI

      10.1002/adsc.202000314

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Site-Selective C(sp3)-H Functionalization of Fluorinated Alkanes Driven by Polar Effects Using a Tungstate Photocatalyst2019

    • Author(s)
      Fukuyama Takahide、Nishikawa Tomohiro、Ryu Ilhyong
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2020 Issue: 10 Pages: 1424-1428

    • DOI

      10.1002/ejoc.201901135

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Controlled [3+2] and [2+2] Cycloadditions of 1,3-Bifunctional Allenes with C60 by Using a Flow Reaction System2019

    • Author(s)
      Ueda Mitsuhiro、Hayama Miho、Hashishita Hiroyuki、Munechika Aiko、Fukuyama Takahide
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2019 Issue: 40 Pages: 6764-6769

    • DOI

      10.1002/ejoc.201901072

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 4,4-Difluoroalkenes by Coupling of α-Substituted α,α-Difluoromethyl Halides with Allyl Sulfones under Photoredox Catalyzed Conditions2019

    • Author(s)
      Uno Misae、Sumino Shuhei、Fukuyama Takahide、Matsuura Makoto、Kuroki Yoshichika、Kishikawa Yosuke、Ryu Ilhyong
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 84 Issue: 14 Pages: 9330-9338

    • DOI

      10.1021/acs.joc.9b00901

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Br-radical-mediated [3+2] Annulation: Synthesis of 2-Bromomethylsubstituted Alkenylcyclopentanes by the Reaction of Alkenylcyclopropanes with Allyl Bromides under Photo irradiation2019

    • Author(s)
      T. Fukuyama, T. Kippo, K. Hamaoka, I. Ryu,
    • Journal Title

      Sci. China Chem

      Volume: 62 Issue: 11 Pages: 1525-1528

    • DOI

      10.1007/s11426-019-9595-0

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Radical Mediated Aza‐Pauson‐Khand Reaction of Acetylenes, Imines, and CO Leading to Five‐Membered Unsaturated Lactams2019

    • Author(s)
      Fukuyama Takahide、Okada Takuma、Nakashima Nao、Ryu Ilhyong
    • Journal Title

      Helvetica Chimica Acta

      Volume: 102 Issue: 10

    • DOI

      10.1002/hlca.201900186

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Kinetically Controlled Fischer Glycosidation under Flow Conditions: A New Method for Preparing Furanosides2019

    • Author(s)
      Fukase Koichi、Masui Seiji、Manabe Yoshiyuki、Hirao Kohtaro、Shimoyama Atsushi、Fukuyama Takahide、Ryu Ilhyong
    • Journal Title

      Synlett

      Volume: 30 Issue: 04 Pages: 397-400

    • DOI

      10.1055/s-0037-1611643

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Bromine-Radical-Mediated Site-Selective Allylation of C(sp3)-H Bonds2019

    • Author(s)
      Ueda Mitsuhiro、Maeda Ayami、Hamaoka Kanako、Sasano Mika、Fukuyama Takahide、Ryu Ilhyong
    • Journal Title

      Synthesis

      Volume: 51 Issue: 05 Pages: 1171-1177

    • DOI

      10.1055/s-0037-1610413

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Carbonylation of Alkyl Radicals Derived from Organosilicates through Visible-Light Photoredox Catalysis2019

    • Author(s)
      Cartier, A.; Levernier, E.; Corce, V.; Fukuyama, T.; Dhimane, A.-L.; Ollivier, C.; Ryu, I,; Fensterbank, L.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 58 Issue: 6 Pages: 1789-1793

    • DOI

      10.1002/anie.201811858

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Electron transfer-induced reduction of organic halides with amines2018

    • Author(s)
      Fukuyama, T.; Fujita, Y.; Miyoshi, H.; Ryu, I. Kao, S.-C.; Wu, Y.-K.
    • Journal Title

      Chem. Commun.

      Volume: 54 Issue: 44 Pages: 5582-5585

    • DOI

      10.1039/c8cc02445f

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Electron-Transfer-Induced Intramolecular Heck Carbonylation Reactions Leading to Benzolactones and Benzolactams2018

    • Author(s)
      Fukuyama, T.; Bando, T.; Ryu, I.
    • Journal Title

      Synthesis

      Volume: 50 Issue: 15 Pages: 3015-3021

    • DOI

      10.1055/s-0037-1609964

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of perinaphthenones through rhodium-catalyzed dehydrative annulation of 1-naphthoic acids with alkynes2018

    • Author(s)
      Fukuyama, T.; Sugimori, T.; Ryu, I
    • Journal Title

      Org. Biomol. Chem.

      Volume: 16 Issue: 41 Pages: 7583-7587

    • DOI

      10.1039/c8ob01453a

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Ionic Liquids Are not Innocent in Pd Catalysis. C-H Arylation of Thiazolium and Imidazolium Ionic Liquids with Aryl Halides,2017

    • Author(s)
      T. Fukuyama, M. T. Rahman, H. Mashima, H. Takahashi, I. Ryu,
    • Journal Title

      Org. Chem. Front.

      Volume: 4 Issue: 9 Pages: 1863-1866

    • DOI

      10.1039/c7qo00331e

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] 新規光反応開発とフローリアクターを用いた光反応の効率化2019

    • Author(s)
      福山高英
    • Organizer
      第54回有機反応若手の会
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] ペルオキソ二硫酸塩を用いた環状ケトンの位置選択的C-Hビニル化反応2019

    • Author(s)
      上川 和也・植田 光洋・福山 高英・柳 日馨
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] フロー系でのアルキンの光ラジカルブロモアリル化反応2019

    • Author(s)
      福山 高英・嶽肩 亜季・笠門 崇好・柳 日馨
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] トラネキサム酸のワンフロー合成2019

    • Author(s)
      草加 達也・福山 高英・大平 雅之・柳 日馨
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] Catalytic Cyclization of Aromatic Carboxylic Acids and Catalytic Reactions in Flow2018

    • Author(s)
      Fukuyama, T.
    • Organizer
      The 1st Hsinchu Workshop on Organic Chemistry
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Rhodium-Catalyzed Dehydrative Annulation of Biaryl Carboxylic Acids with Alkynes2018

    • Author(s)
      Fukuyama, T.; Sakate, T.; Ryu, I.
    • Organizer
      The Fourth International Symposium on C-H Activation
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Recent Advances for Heterogeneous Catalysis in Flow2017

    • Author(s)
      T. Fukuyama
    • Organizer
      Asia Pacific Confederation of Chemical Engineers Congress
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Efficient Flow Photoreactions Using Photo-Microreactor2017

    • Author(s)
      T. Fukuyama
    • Organizer
      ISONIS-11&ISMMS-3
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 有機合成におけるフロー反応装置の利用2017

    • Author(s)
      福山 高英
    • Organizer
      化学工学会関西支部 マイクロプロセス最前線シリーズ
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] 有機合成におけるフロー反応装置の利用2017

    • Author(s)
      福山 高英
    • Organizer
      第29回グリーンケミストリーフォーラム
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] Synthesis of Thiochromenones via Rh-Catalyzed Annulation of Thiosalicylic Acids with Alkynes2017

    • Author(s)
      T. Fukuyama, T. Sugimori, I. Ryu
    • Organizer
      OMCOS19
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Rhodium-Catalyzed Reaction of Biarylcarboxylic Acids with Alkynes Leading to Phenanthrenes2017

    • Author(s)
      T. Fukuyama, T. Sakate, I. Ryu
    • Organizer
      OMCOS19
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Rh-Catalyzed Synthesis of Quinolinone Derivatives by Carboamination of Anthranilic Acids to Alkynes2017

    • Author(s)
      T. Fukuyama, T. Furukawa, I. Ryu
    • Organizer
      OMCOS19
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research

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Published: 2017-04-28   Modified: 2021-02-19  

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