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Application Wheel-Shaped Cationic Complexes to Catalytic Molecular Transformations

Research Project

Project/Area Number 21K14627
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionOsaka University

Principal Investigator

Nishii Yuji  大阪大学, 大学院工学研究科, 准教授 (70773787)

Project Period (FY) 2021-04-01 – 2024-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2022: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2021: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Keywords有機分子触媒 / トリプチセン / ハロゲン / 芳香族化合物 / カチオン / 求電子置換反応 / 有機機能性材料 / ナノカーボン
Outline of Research at the Start

本研究では、トリプチセン骨格によって誘起される特異な活性化メカニズムを理解し、芳香族分子に対する新機軸の化学修飾法として一般化することにある。ハロゲンの活性化に限らず、多様な求電子試薬を「高反応性カチオンとして芳香環に届ける」触媒反応系を構築することにより、従来法では実現できなかった高難度反応を達成する。この合成技術の確立は、付加価値の高い化合物群への迅速なアクセスを可能とし、新たな学問領域を開拓するための合成ツールとして活用が期待できる。

Outline of Final Research Achievements

Based on the previous study on TripSMe-catalyzed aromatic halogenation reaction, new catalytic reactions were establish and a novel catalyst platform was developed. In particular; (1) DFT calculations revealed the effect of molecular structure and charge distribution on catalytic performance, (2) metal-free direct trifluoromethylthiolation reaction was developed, and (3) several boron cluster compounds were found to be effective catalyst platform for the aromatic halogenation reactions.

Academic Significance and Societal Importance of the Research Achievements

本研究の遂行により、機能性に優れた有機分子触媒の開発に向け、新たな設計指針を提案することができた。この成果は有機合成プロセスの効率化に貢献するとともに、従来法では構築の困難であった分子構造へのアクセスを可能とする。こうした観点から、有機光電子デバイスの開発や超分子化学、有機金属化学といった関連分野に波及効果を及ぼすものと期待できる。

Report

(4 results)
  • 2023 Annual Research Report   Final Research Report ( PDF )
  • 2022 Research-status Report
  • 2021 Research-status Report
  • Research Products

    (29 results)

All 2024 2023 2022 2021 Other

All Journal Article (16 results) (of which Peer Reviewed: 16 results,  Open Access: 1 results) Presentation (9 results) (of which Int'l Joint Research: 3 results,  Invited: 2 results) Remarks (3 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Aromatic halogenation using carborane catalyst2024

    • Author(s)
      Kona Chandrababu Naidu、Oku Rikuto、Nakamura Shotaro、Miura Masahiro、Hirano Koji、Nishii Yuji
    • Journal Title

      Chem

      Volume: 10 Issue: 1 Pages: 402-413

    • DOI

      10.1016/j.chempr.2023.10.006

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Tunable mechanochromic luminescence of benzofuran-fused pyrazine: effects of alkyl chain length and branching pattern2024

    • Author(s)
      Nakamura Shotaro、Okubo Kohei、Nishii Yuji、Hirano Koji、Tohnai Norimitsu、Miura Masahiro
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 12 Issue: 7 Pages: 2370-2378

    • DOI

      10.1039/d3tc04748b

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Rhodium-Catalyzed Isoquinoline Synthesis Using Vinyl Selenone as Oxidizing Acetylene Surrogate2023

    • Author(s)
      Inami Ayumi、Nishii Yuji、Hirano Koji、Miura Masahiro
    • Journal Title

      Organic Letters

      Volume: 25 Issue: 18 Pages: 3206-3209

    • DOI

      10.1021/acs.orglett.3c00826

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stimuli‐Responsive Properties on a Bisbenzofuropyrazine Core: Mechanochromism and Concentration‐Controlled Vapochromism2023

    • Author(s)
      Nakamura Shotaro、Okubo Kohei、Nishii Yuji、Hirano Koji、Tohnai Norimitsu、Miura Masahiro
    • Journal Title

      Chemistry A European Journal

      Volume: 29 Issue: 68

    • DOI

      10.1002/chem.202302605

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Isoselenazole Synthesis by Rh-Catalyzed Direct Annulation of Benzimidates with Sodium Selenite2023

    • Author(s)
      Xu-Xu Qing-Feng、Nishii Yuji、Miura Masahiro
    • Journal Title

      Chemistry

      Volume: 5 Issue: 4 Pages: 2068-2074

    • DOI

      10.3390/chemistry5040140

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Axially Chiral Bibenzo[g]coumarin Derivatives by Rhodium-Catalyzed Oxidative Annulation of Thiocarbamates2023

    • Author(s)
      Nishii Yuji、Miura Masahiro、Takishima Ryo、Ghosh Koushik
    • Journal Title

      Synlett

      Volume: - Issue: 08 Pages: 925-929

    • DOI

      10.1055/a-2202-4667

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Direct Vinylene Annulation of 2-Aryloxazolines and Cascade Ring-Opening Using a Vinyl Selenone2023

    • Author(s)
      Nishii Yuji、Miura Masahiro、Kitano Junya、Hirano Koji
    • Journal Title

      Synlett

      Volume: -

    • DOI

      10.1055/a-2214-5299

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium‐Catalyzed α‐Selective Halogenation of Triptycene Using Sulfur Directing Group2023

    • Author(s)
      Ueno Keisuke、Nishii Yuji、Hirano Koji、Miura Masahiro
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 12 Issue: 12

    • DOI

      10.1002/ajoc.202300588

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective Synthesis of C4-Functionalized Benzofurans by Rhodium-Catalyzed Vinylene Transfer: Computational Study on the Cyclopentadienyl Ligand2022

    • Author(s)
      Kitano Junya、Nishii Yuji、Miura Masahiro
    • Journal Title

      Organic Letters

      Volume: 24 Issue: 31 Pages: 5679-5683

    • DOI

      10.1021/acs.orglett.2c02030

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Diarylselenides through Rh-Catalyzed Direct Diarylation of Elemental Selenium with Benzamides2022

    • Author(s)
      Xu-Xu Qing-Feng、Nishii Yuji、Miura Masahiro
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 87 Issue: 24 Pages: 16887-16894

    • DOI

      10.1021/acs.joc.2c02131

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Structure, and Chiroptical Properties of Indolo‐ and Pyridopyrrolo‐Carbazole‐Based C2‐Symmetric Azahelicenes2021

    • Author(s)
      T. Taniguchi, U. Nishii, T. Mori, K. Nakayama, M. Miura
    • Journal Title

      Chem. Eur. J.

      Volume: 27 Issue: 26 Pages: 1-7

    • DOI

      10.1002/chem.202100327

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Peri-Selective Direct Acylmethylation and Amidation of Naphthalene Derivatives Using Iridium and Rhodium Catalysts2021

    • Author(s)
      Nishii Yuji、Miura Masahiro、Kona Chandrababu Naidu、Oku Rikuto
    • Journal Title

      Synthesis

      Volume: 53 Issue: 17 Pages: 3126-3136

    • DOI

      10.1055/a-1472-1059

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Electrophilic Substitution of Asymmetrically Distorted Benzenes within Triptycene Derivatives2021

    • Author(s)
      Ueno Keisuke、Nishii Yuji、Miura Masahiro
    • Journal Title

      Organic Letters

      Volume: 23 Issue: 9 Pages: 3552-3556

    • DOI

      10.1021/acs.orglett.1c00970

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Rhodium-catalysed direct formylmethylation using vinylene carbonate and sequential dehydrogenative esterification2021

    • Author(s)
      Kato Moena、Ghosh Koushik、Nishii Yuji、Miura Masahiro
    • Journal Title

      Chemical Communications

      Volume: 57 Issue: 67 Pages: 8280-8283

    • DOI

      10.1039/d1cc03362j

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Sulfur-Directed C7-Selective Alkenylation of Indoles under Rhodium Catalysis2021

    • Author(s)
      Kona Chandrababu Naidu、Nishii Yuji、Miura Masahiro
    • Journal Title

      Organic Letters

      Volume: 23 Issue: 16 Pages: 6252-6256

    • DOI

      10.1021/acs.orglett.1c01990

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Benzoisoselenazolones via Rh(III)‐Catalyzed Direct Annulative Selenation by Using Elemental Selenium2021

    • Author(s)
      Xu‐Xu Qing‐Feng、Nishii Yuji、Uetake Yuta、Sakurai Hidehiro、Miura Masahiro
    • Journal Title

      Chemistry - A European Journal

      Volume: 27 Issue: 71 Pages: 17952-17959

    • DOI

      10.1002/chem.202103485

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Presentation] Aromatic Halogenation Using Carborane Catalyst2023

    • Author(s)
      Yuji Nishii, Chandrababu Naidu Kona, Rikuto Oku, Shotaro Nakamura, Masahiro Miura, Koji Hirano
    • Organizer
      16th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-16)
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] New Lewis Base Catalysts for Aromatic Halogenation2023

    • Author(s)
      Yuji Nishii, Chandrababu Naidu Kona, Rikuto Oku, Shotaro Nakamura, Koji Hirano, Masahiro Miura
    • Organizer
      21st International Symposium on Organometallic Chemistry Directed Toward Organic Synthesis (OMCOS 21)
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Spinyカルボラン触媒を用いた芳香族ハロゲン化反応2023

    • Author(s)
      西井祐二、中村彰太郎、三浦雅博、平野康次
    • Organizer
      第33回基礎有機化学討論会
    • Related Report
      2023 Annual Research Report
  • [Presentation] カルボランスルフィド触媒による芳香族化合物の求電子的ハロゲン化反応2023

    • Author(s)
      西井祐二、Chandrababu Naidu Kona、奥陸人、中村彰太郎、平野康次、三浦雅博
    • Organizer
      第50回有機典型元素化学討論会
    • Related Report
      2023 Annual Research Report
  • [Presentation] Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation2022

    • Author(s)
      Yuji Nishii
    • Organizer
      International Congress on Pure & Applied Chemistry Kota Kinabalu (ICPAC KK) 2022
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Selective Synthesis of C4-Substituted Benzofurans Through Rhodium-Catalyzed Vinylene Transfer2022

    • Author(s)
      北野 淳也, 西井 祐二, 三浦 雅博
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2022 Research-status Report
  • [Presentation] Rhodium-Catalyzed Site-Selective Direct Amidation of Naphthalenes Using Sulfur Directing Group2022

    • Author(s)
      奥 陸人, C. N. Kona, 西井 祐二, 三浦 雅博
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2022 Research-status Report
  • [Presentation] Selective Synthesis of C4-Substituted Benzofurans by Catalytic Vinylene Transfer Reaction2022

    • Author(s)
      西井 祐二, 三浦 雅博
    • Organizer
      第51回 複素環化学討論会
    • Related Report
      2022 Research-status Report
  • [Presentation] 芳香族求電子的ハロゲン化反応に対する高活性スルフィド触媒の開発2021

    • Author(s)
      西井 祐二、三浦 雅博
    • Organizer
      第31回基礎有機化学討論会
    • Related Report
      2021 Research-status Report
  • [Remarks] Researchmap

    • URL

      https://researchmap.jp/y_nishii

    • Related Report
      2023 Annual Research Report
  • [Remarks] 大阪大学工学研究科 平野研究室

    • URL

      https://www-chem.eng.osaka-u.ac.jp/hirano-lab/index.html

    • Related Report
      2022 Research-status Report
  • [Remarks] 反応分子化学領域ホームページ

    • URL

      http://www.chem.eng.osaka-u.ac.jp/~miura-lab/index.html

    • Related Report
      2021 Research-status Report
  • [Patent(Industrial Property Rights)] カルボラン化合物及びそれを用いたハロゲン化芳香族化合物の製造方法2023

    • Inventor(s)
      西井祐二
    • Industrial Property Rights Holder
      西井祐二
    • Industrial Property Rights Type
      特許
    • Filing Date
      2023
    • Related Report
      2023 Annual Research Report

URL: 

Published: 2021-04-28   Modified: 2025-01-30  

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