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Innovative metal-free oxidative bond formation of aromatic compounds having heteroatoms

Research Project

Project/Area Number 17K08230
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionRitsumeikan University

Principal Investigator

Morimoto Koji  立命館大学, 薬学部, 助教 (10543952)

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: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2018: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywords超原子価ヨウ素 / ヘテロ原子 / グリコシル化 / カップリング / 窒素 / ヨウ素 / 芳香族化合物 / 有機化学
Outline of Final Research Achievements

The bond formation reaction by the oxidation of an aromatic compound having a hetero atom is an extremely important reaction in terms of synthetic chemistry and biosynthetic mechanism. In this study, we developed a bond formation reaction by activation of heteroatoms using a hypervalent iodine reagent. The establishment of this method has become a new alternative to the coupling reaction using transition metals, which is currently widely used.

Academic Significance and Societal Importance of the Research Achievements

有機化合物中の触媒を用いて結合させるクロスカップリング反応は、日本で生まれた化学分野の革新技術として世界からも高く評価され、その応用は多岐にわたっている。現在最も汎用されているクロスカップリング反応は、レアメタルであるパラジウムを用いた根岸カップリングや鈴木カップリングに代表される手法であるが触媒として高価なレアメタルを用い、芳香環にハロゲンやメタルを導入して官能基化を行う必要があり、そのために反応工程が長くなることが課題とされている。本手法の確立は、現在汎用とされている遷移金属を用いたクロスカップリング反応に代わるものとして期待できる。

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

All Journal Article (11 results) (of which Peer Reviewed: 6 results,  Open Access: 6 results,  Acknowledgement Compliant: 1 results) Presentation (18 results) (of which Int'l Joint Research: 4 results,  Invited: 2 results)

  • [Journal Article] N-Glycosylation Reaction of Thio-Glycoside Using Hypervalent Iodine(Ill) Reagent2020

    • Author(s)
      Morimoto Koji、Yanase Kana、Ikeda Takumi、Uchikawa Chihiro、Kita Yasuyuki、Kajimoto Tetsuya
    • Journal Title

      HETEROCYCLES

      Volume: 101 Issue: 2 Pages: 621-630

    • DOI

      10.3987/com-19-s(f)53

    • Related Report
      2019 Annual Research Report
  • [Journal Article] Metal-Free Oxidative Cross-Coupling Reaction of Heteroaromatic and Related Compounds2019

    • Author(s)
      Morimoto Koji
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 67 Issue: 12 Pages: 1259-1270

    • DOI

      10.1248/cpb.c19-00286

    • NAID

      130007754111

    • ISSN
      0009-2363, 1347-5223
    • Year and Date
      2019-12-01
    • Related Report
      2019 Annual Research Report
  • [Journal Article] Controlled-coupling of quinone monoacetals by new activation methods: Regioselective synthesis of phenol-derived compounds2019

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

      Synlett

      Volume: 30 Issue: 10 Pages: 1125-1143

    • DOI

      10.1055/s-0037-1611735

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 超原子価ヨウ素反応剤を活性化剤としたグリコシル化反応の開発2019

    • Author(s)
      森本功治、北泰行、梶本哲也
    • Journal Title

      化学工業

      Volume: 70 Pages: 650-657

    • Related Report
      2019 Annual Research Report
  • [Journal Article] Enviromentally-Benign Glycosylation Reaction Using Odorless Thio-Glycosides and Hypervalent Iodine(III) Reagent2019

    • Author(s)
      Kita Yasuyuki、Kajimoto Tetsuya、Morimoto Koji、Yanase Kana、Odaka Ibuki
    • Journal Title

      HETEROCYCLES

      Volume: 99 Issue: 1 Pages: 680-680

    • DOI

      10.3987/com-18-s(f)35

    • Related Report
      2018 Research-status Report
  • [Journal Article] Selective carboxylation of reactive benzylic C-H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system2018

    • Author(s)
      Dohi Toshifumi、Ueda Shohei、Iwasaki Kosuke、Tsunoda Yusuke、Morimoto Koji、Kita Yasuyuki
    • Journal Title

      Beilstein Journal of Organic Chemistry

      Volume: 14 Pages: 1087-1094

    • DOI

      10.3762/bjoc.14.94

    • Related Report
      2018 Research-status Report
    • Open Access
  • [Journal Article] Metal-free oxidative cross-coupling of pyrroles with electron-rich arenes using recyclable hypervalent iodine(III) reagent2018

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

      Heterocycles

      Volume: 97 Issue: 1 Pages: 632-645

    • DOI

      10.3987/com-18-s(t)52

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Oxidative biaryl coupling of N-aryl anilines using hypervalent iodine(III) reagent2017

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

      Synlett

      Volume: 28 Issue: 20 Pages: 2941-2945

    • DOI

      10.1055/s-0036-1590875

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Selective aryl radical transfers into N-heteroaromatics from diaryliodonoium salts with trimethoxybenzene auxiliary2017

    • Author(s)
      T. Dohi, S. Ueda, A. Hirai, Y. Kojima, K. Morimoto, Y. Kita
    • Journal Title

      Heterocycles

      Volume: 95 Issue: 2 Pages: 1272-1284

    • DOI

      10.3987/com-16-s(s)90

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Metal-free Oxidative Cross-Coupling Reaction of Aromatic Compounds Containing Heteroatoms2017

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

      Synlett

      Volume: 28 Issue: 14 Pages: 1680-1694

    • DOI

      10.1055/s-0036-1588455

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Metal-free O-arylation of carboxylic acid by active diaryliodonium(III) intermediates generated in situ from iodosoarenes2017

    • Author(s)
      Dohi T., Koseki D., Sumida K., Okada K., Mizuno S., Kato A., Morimoto K., Kita Y.
    • Journal Title

      Adv. Synth. Catal.

      Volume: 359 Issue: 20 Pages: 3503-3508

    • DOI

      10.1002/adsc.201700843

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] 超原子価ヨウ素反応剤を用いたチオグリコシドとアゾール類とのN-グリコシル化反応2020

    • Author(s)
      森本功治、柳瀬伽奈、池田拓未、内川千尋、北 泰行、梶本哲也
    • Organizer
      日本薬学会第140年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Hypervalent Iodine(III) Induced Oxidative Cross-Coupling of Phenols2019

    • Author(s)
      K. Morimoto, K. Toda, H. Takeuchi, T. Dohi, Y. Kita
    • Organizer
      27th International Society of Heterocyclic Chemistry
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] N-Glycosylation Reaction of Thioglycoside using Hypervalent Iodine(III) Reagent2019

    • Author(s)
      K. Morimoto, K. Yanase, T. Ikeda, C. Uchikawa, Y. Kita, T. Kajimoto
    • Organizer
      27th International Society of Heterocyclic Chemistry
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 超原子価ヨウ素反応剤をチオグリコシドの活性化剤に用いたトリアゾール類とのN-グリコシル化反応2019

    • Author(s)
      森本功治、柳瀬伽奈、池田拓未、内川千尋、北 泰行、梶本哲也
    • Organizer
      第69回日本薬学会関西支部総会・大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 超原子価ヨウ素反応剤を用いたチオグリコシドとアゾール類とのN-グリコシル化反応2019

    • Author(s)
      森本功治、柳瀬伽奈、池田拓未、内川千尋、北 泰行、梶本哲也
    • Organizer
      第45回反応と合成の進歩シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] Hypervalent Iodine(III) Reagent Induced N-Glycosylation Reaction of Thioglycoside2019

    • Author(s)
      K. Morimoto, K. Yanase, T. Ikeda, C. Uchikawa, Y. Kita, T. Kajimoto
    • Organizer
      第12回有機触媒シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] 超原子価ヨウ素反応剤を活性化剤とするチオグリコシドのグリコシル化反応の開発2018

    • Author(s)
      森本 功治
    • Organizer
      第37回日本糖質学会年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 超原子価ヨウ素反応剤を用いた新規グルクロニル化反応の開発2018

    • Author(s)
      森本 功治
    • Organizer
      第44回反応と合成の進歩シンポジウム
    • Related Report
      2018 Research-status Report
  • [Presentation] Glucuronydation Reaction using Hypervalent Iodine(III) as an Excellent Promoter2018

    • Author(s)
      Koji Morimoto
    • Organizer
      The 6th International Conference on Hypervalent Iodine Chemistry (ICHIC 2018)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] 超原子価ヨウ素反応剤を活性化剤としたグルクロニル化反応の開発2018

    • Author(s)
      森本 功治
    • Organizer
      第 11 回有機触媒シンポジウム
    • Related Report
      2018 Research-status Report
  • [Presentation] ヘテロ芳香族及び関連化合物のメタルフリー酸化的結合形成反応2017

    • Author(s)
      森本功治
    • Organizer
      第3回近畿薬学シンポジウム:化学系の若い力
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] Organo-Iodine(III) Catalyzed Oxidative Cross-coupling of Phenols2017

    • Author(s)
      K. Morimoto. K. Samkamoto, T. Dohi, Y. Kita
    • Organizer
      26th International Society of Heterocyclic Chemistry Congress
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] ヘテロ原子を有する芳香族化合物類の革新的なメタルフリー酸化的結合形成2017

    • Author(s)
      森本功治
    • Organizer
      産研若手合成セミナー
    • Related Report
      2017 Research-status Report
  • [Presentation] 超原子価ヨウ素反応剤を用いた N-アリールアニリン類の酸化的カップリング反応2017

    • Author(s)
      森本功治 、小関大地 、土肥寿文 、北 泰行
    • Organizer
      第 67 回 日本薬学会近畿支部総会・大会
    • Related Report
      2017 Research-status Report
  • [Presentation] キノンモノアセタールとフェノール類のクロスカップリングを応用した縮環ベンゾフラン合成2017

    • Author(s)
      上田中 徹 坪島昂平 森本功治 土肥寿文 北 泰行
    • Organizer
      第 47 回 複素環化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] ヘテロ原子を有する芳香族化合物類の革新的なメタルフリー酸化的結合形成2017

    • Author(s)
      森本功治
    • Organizer
      第43回 反応と合成の進歩シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] ヘテロ原子を有する芳香族化合物類の革新的なメタルフリー酸化的結合形成2017

    • Author(s)
      森本功治
    • Organizer
      近畿大学 若手セミナー
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] 有機ヨウ素触媒を用いたフェノール類の酸化的クロスカップリング反応2017

    • Author(s)
      森本功治、坂本一真、高橋優介、土肥寿文、北 泰行
    • Organizer
      第10回有機触媒シンポジウム
    • Related Report
      2017 Research-status Report

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

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