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2023 Fiscal Year Annual Research Report

Development of SpiroBipyridine Ligands for Efficient and Selective C-H Activation

Publicly Offered Research

Project AreaDigitalization-driven Transformative Organic Synthesis (Digi-TOS)
Project/Area Number 22H05384
Research InstitutionInstitute of Physical and Chemical Research

Principal Investigator

イリエシュ ラウレアン  国立研究開発法人理化学研究所, 環境資源科学研究センター, チームリーダー (40569951)

Project Period (FY) 2022-06-16 – 2024-03-31
Keywordsorganic synthesis
Outline of Annual Research Achievements

The purpose of this research is the development of new spirobipyridine ligands and of reaction conditions for the efficient and site-selective catalytic functionalization of arenes. During FY2023, we performed a mechanistic study by computations and an unprecedented ligand kinetic isotope effect to prove that a noncovalent interaction between a C-H bond of the spirobipyridine ligand's backbone and the pi electrons of the arene substrate can accelerate the iridium-catalyzed activation of arenes.
We also developed spirobipyridine ligands bearing hydroxyl (OH) groups capable of recognizing pyridine substrates through hydrogen bonding, and both accelerate and control the site selectivity in iridium-catalyzed borylation.
Finally, we developed a spirobipyridine ligand that enables meta-selective iridium-catalyzed silylation of monosubstituted arenes.

Research Progress Status

令和5年度が最終年度であるため、記入しない。

Strategy for Future Research Activity

令和5年度が最終年度であるため、記入しない。

  • Research Products

    (25 results)

All 2024 2023 Other

All Int'l Joint Research (1 results) Journal Article (2 results) (of which Peer Reviewed: 2 results,  Open Access: 1 results) Presentation (20 results) (of which Int'l Joint Research: 9 results,  Invited: 10 results) Remarks (2 results)

  • [Int'l Joint Research] National Institute of Material Physics(ルーマニア)

    • Country Name
      ROMANIA
    • Counterpart Institution
      National Institute of Material Physics
  • [Journal Article] Noncovalent interaction with a spirobipyridine ligand enables efficient iridium-catalyzed C-H activation2024

    • Author(s)
      Jin Yushu、Ramadoss Boobalan、Asako Sobi、Ilies Laurean
    • Journal Title

      Nature Communications

      Volume: 15 Pages: 2886

    • DOI

      10.1038/s41467-024-46893-6

    • Peer Reviewed / Open Access
  • [Journal Article] Remote Steric Control for Site-Selective Synthesis2023

    • Author(s)
      Asako Sobi、Ilies Laurean
    • Journal Title

      Synlett

      Volume: 34 Pages: 2110~2116

    • DOI

      10.1055/a-2126-1835

    • Peer Reviewed
  • [Presentation] Substrate Recognition and Reaction Control by Functional Spirobipyridines2024

    • Author(s)
      Asako Sobi, Jin Yushu, Ramadoss Boobalan, De Bhusan Pinaki, Ilies Laurean
    • Organizer
      CEMS International Symposium on Supramolecular Chemistry and Functional Materials 2024
  • [Presentation] Remote Regiocontrol in Iridium-Catalyzed C-H Silylation of Arenes Enabled by SpiroBipyridine Ligand2024

    • Author(s)
      Jin Yushu, Sekar Jayakumar, Asako Sobi, Ilies Laurean
    • Organizer
      The 104th CSJ Annual Meeting
  • [Presentation] Ligand-Enabled Iridium-Catalyzed Regiodivergent C-H Borylation of Pyridines and Quinolines2024

    • Author(s)
      De Bhusan Pinaki, Okamoto Kazuhiro, Asako Sobi, Ilies Laurean
    • Organizer
      The 104th CSJ Annual Meeting
  • [Presentation] Development of catalytic systems for selective organic transformations2023

    • Author(s)
      Laurean Ilies
    • Organizer
      Smart Diaspora 2023, Exploratory Workshop: Transboundary Chemistry at the Forefront of Molecular Sciences
    • Int'l Joint Research / Invited
  • [Presentation] Catalyst Design for Selective and Efficient Reactions2023

    • Author(s)
      Laurean Ilies
    • Organizer
      Seminar on Organic Molecule Transformations of Institute for Chemical Research, Kyoto University
    • Invited
  • [Presentation] Catalyst-Enabled Selective Functionalization of Arenes2023

    • Author(s)
      Laurean Ilies
    • Organizer
      Tateshina Conference on Organic Chemistry
  • [Presentation] Design of New Ligands for Selective & Efficient Catalytic Transformations2023

    • Author(s)
      Laurean Ilies
    • Organizer
      International Virtual Conference on “Recent Trends in Organometallics and Material Science"
    • Int'l Joint Research / Invited
  • [Presentation] Ligand Design for Regioselective C-H Activation2023

    • Author(s)
      Laurean Ilies
    • Organizer
      The 22nd European Symposium on Organic Chemistry
    • Int'l Joint Research / Invited
  • [Presentation] My Research Journey in Japan2023

    • Author(s)
      Laurean Ilies
    • Organizer
      Seminar of the Faculty of Chemistry and Chemical Engineering, Babes-Bolyai University
    • Int'l Joint Research / Invited
  • [Presentation] Spirobipyridine Ligand for Remote Steric Control in Iridium-Catalyzed C-H Borylation of Arenes2023

    • Author(s)
      Asako Sobi, Jin Yushu, Ramadoss Boobalan, Ilies Laurean
    • Organizer
      21st International Symposium on Organometallic Chemistry Directed Toward Organic Synthesis
    • Int'l Joint Research
  • [Presentation] スピロビピリジン:イリジウム触媒によるC-Hホウ素化反応における遠隔位立体制御および反応加速2023

    • Author(s)
      Asako Sobi, Jin Yushu, Ramadoss Boobalan, Ilies Laurean
    • Organizer
      第33回基礎有機化学討論会
  • [Presentation] Iridium-Catalyzed Regioswitchable C-H Borylation Enabled by Hydroxyspirobipyridine Ligands2023

    • Author(s)
      Pinaki Bhusan De, Kazuhiro Okamoto, Sobi Asako, Laurean Ilies
    • Organizer
      The 69th Symposium on Organometallic Chemistry
  • [Presentation] Catalyst Design for Selective and Efficient Reactions2023

    • Author(s)
      Laurean Ilies
    • Organizer
      第16回ChemBioハイブリッドレクチャー
    • Invited
  • [Presentation] Remote steric control and acceleration in iridium-catalyzed C-H borylation of arenes enabled by spirobipyridine ligand2023

    • Author(s)
      Asako Sobi, Jin Yushu, Ramadoss Boobalan, Ilies Laurean
    • Organizer
      The XXIII International Conference on Organic Synthesis
    • Int'l Joint Research
  • [Presentation] 配位子設計による選択的なC-H結合変換反応の開発2023

    • Author(s)
      Laurean Ilies
    • Organizer
      近畿化学協会有機金属部会第3回例会
    • Invited
  • [Presentation] Spirobipyridine Enables Remote Steric Control and Rate Acceleration in Iridium-Catalyzed Aromatic C-H Borylation2023

    • Author(s)
      Asako Sobi, Jin Yushu, Ramadoss Boobalan, Ilies Laurean
    • Organizer
      The 15th International Kyoto Conference on New Aspects of Organic Chemistry
    • Int'l Joint Research
  • [Presentation] Catalyst Design for Selectivity and Reactivity2023

    • Author(s)
      Laurean Ilies
    • Organizer
      Seminar of the Faculty of Chemistry, University of Bucharest
    • Int'l Joint Research / Invited
  • [Presentation] Catalyst Design for Selectivity and Reactivity2023

    • Author(s)
      Laurean Ilies
    • Organizer
      Seminar of the National Institute of Material Physics, Magurele
    • Int'l Joint Research / Invited
  • [Presentation] Remote Substrate Recognition for Selectivity and Reactivity2023

    • Author(s)
      Laurean Ilies
    • Organizer
      International Joint Symposium 2023 on Synthetic Organic Chemistry
  • [Presentation] 触媒設計による選択的・効率的な合成反応の開発2023

    • Author(s)
      Laurean Ilies
    • Organizer
      理研シンポジウム 「第 21 回 分析・解析技術と化学の最先端」
    • Invited
  • [Remarks] “弱い相互作用”で炭化水素資源の変換反応を大きく加速

    • URL

      https://www.riken.jp/press/2024/20240417_4/index.html

  • [Remarks] Ilies Team Home Page

    • URL

      http://iliesteam.riken.jp/home.html

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Published: 2024-12-25  

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