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Development of New Catalytic Reactions Based on New Elementene Species

Research Project

Project/Area Number 18H01976
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionKyoto University

Principal Investigator

Ohe Kouichi  京都大学, 工学研究科, 教授 (90213636)

Co-Investigator(Kenkyū-buntansha) 岡本 和紘  京都大学, 工学研究科, 助教 (30552658)
Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥18,070,000 (Direct Cost: ¥13,900,000、Indirect Cost: ¥4,170,000)
Fiscal Year 2020: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Fiscal Year 2019: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Fiscal Year 2018: ¥12,610,000 (Direct Cost: ¥9,700,000、Indirect Cost: ¥2,910,000)
Keywordsニトレン / 含窒素複素環 / 不斉合成 / シリレン / ゲルミレン / ホスフィニデン / α-アミノ酸 / ボリレン / 二環性ヘテロサイクル / 有機不飽和活性種 / 触媒反応 / キラル触媒 / 複素環 / α-アミノ酸誘導体
Outline of Final Research Achievements

A new approach to a range of elementene species, such as carbenes and nitrenes allows us to develop the new methodology to incorporate such species into organic products and complexes composed of transition metals. To comprehensively exploit the elementene chemistry, the rational design and synthesis of thermodynamically stabilized precursors for elementene species are highly demanded. In the course of this study, we successfully developed new methodologies incorporating elementene species in heterocyclic organic compounds and complexes of transition metals by using cyclic precursors.

Academic Significance and Societal Importance of the Research Achievements

カルベンやニトレンに代表されるエレメンテン(原子価結合欠損型活性種の総称)は,高活性で短寿命のためフラスコ中で保存できない。したがって,取扱いの容易な前駆体の設計は重要な意味を持つ。我々は,従来の発生法とは異なる反応性原理に基づき,高い安定性を持ち,分子内に比較的結合エネルギーの小さい結合を有する環状化合物前駆体を開発した。これを用いることによって,様々な遷移金属錯体触媒を用いて,エレメンテンを取り込ませた新規有機化合物の合成法開発に成功した。これらの成果は、新物質開発の方法論を大きく変えうる新手法の重要性を示した。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • Research Products

    (18 results)

All 2021 2020 2019 2018 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (7 results) (of which Int'l Joint Research: 1 results,  Invited: 5 results) Book (2 results) Remarks (2 results)

  • [Journal Article] Properties and Reactivities of Zwitterionic Platinum(II)-ate Complexes Generated by Transforming Coordination of an Alkyne-Bisphosphine Ligand2021

    • Author(s)
      K. Okamoto, K. Sasakura, S. Funasaka, H. Watanabe, M. Suezaki, and K. Ohe
    • Journal Title

      Organometallics

      Volume: 40 Issue: 7 Pages: 848-856

    • DOI

      10.1021/acs.organomet.0c00759

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chemistry of 2H-Azirines from Old to New — Selective Synthesis and Transformation2020

    • Author(s)
      岡本和紘,江口 輝,大江浩一
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 78 Issue: 12 Pages: 1126-1137

    • DOI

      10.5059/yukigoseikyokaishi.78.1126

    • NAID

      130007951778

    • ISSN
      0037-9980, 1883-6526
    • Year and Date
      2020-12-01
    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The Reaction Pathway Leading to Dinuclear Rhodium and Iridium Complexes from Alkyne-containing Bisphosphine Ligands2020

    • Author(s)
      K. Sasakura, K. Okamoto, S. Sakaki, K. Ohe
    • Journal Title

      Bulletin of The Chemical Society

      Volume: - Issue: 6 Pages: 794-798

    • DOI

      10.1246/bcsj.20200036

    • NAID

      130007856023

    • Related Report
      2020 Annual Research Report 2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Bimetallic Reactivities of Dinuclear Iridium and Rhodium Complexes Generated from Two Types of Alkyne-containing Bisphosphine Ligands2020

    • Author(s)
      K. Sasakura, K. Okamoto, K. Ohe
    • Journal Title

      European Journal of Inorganic Chemistry

      Volume: - Issue: 19 Pages: 1894-1901

    • DOI

      10.1002/ejic.202000132

    • Related Report
      2020 Annual Research Report 2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Recent Progress on Cyclic Nitrenoid Precursors in Transition-metal-catalyzed Nitrene-transfer Reactions2019

    • Author(s)
      T. Shimbayashi, K. Sasakura, A. Eguchi, K. Okamoto, K. Ohe
    • Journal Title

      Chem. Eur. J.

      Volume: 25 Issue: 13 Pages: 3156-3180

    • DOI

      10.1002/chem.201803716

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Selective Formation of Substituted Pyrroles from Alkene-tethered Cyclic Oxime Esters2018

    • Author(s)
      Kazuhiro Okamoto, Tomohiro Oda, Gaku Matsushita, Takuya Shimbayashi, Kohei Sasakura, and Kouichi Ohe
    • Journal Title

      Heterocycles

      Volume: 97 Issue: 1 Pages: 218-231

    • DOI

      10.3987/com-17-s(t)4

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Divergent Catalytic Approach from Cyclic Oxime Esters to Nitrogen-Containing Heterocycles with Group 9 Metal Catalysts2018

    • Author(s)
      Takuya Shimbayashi, Gaku Matsushita, Atsushi Nanya, Akira Eguchi, Kazuhiro Okamoto, and Kouichi Ohe
    • Journal Title

      ACS Catalysis

      Volume: 8 Issue: 9 Pages: 7773-7780

    • DOI

      10.1021/acscatal.8b01646

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Presentation] Ir-Ir結合を有する1,3-ブタジエン-1,4-ジイル錯体における配位子置換反応および11族金属イオンの取りこみ2020

    • Author(s)
      笹倉康平、岡本和紘、大江浩一
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 軸性キラリティーを有する3,3'-二置換2,2'-ビピリジン配位子を有する二核白金錯体の合成と光学特性2020

    • Author(s)
      末崎雅大、笹倉康平、岡本和紘、三木康嗣、大江浩一
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] オキシム誘導体を利用する鉄触媒ラジカル反応2019

    • Author(s)
      大江浩一
    • Organizer
      第6回次世代の有機化学・広島シンポジウム
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Iron-Catalyzed Radical Reactions Based on N-O Bond Cleavage of Oxime Derivatives2019

    • Author(s)
      K. Ohe
    • Organizer
      The 14th Kinki-Youngnam Joint Symposium on Organometallic Chemistry
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Iron-Catalyzed Radical Reactions Triggered by N-O Bond Cleavage of Oxime Derivatives2019

    • Author(s)
      K. Ohe
    • Organizer
      The 8th Kansai-CMDS Meeting on OMCOS, 2019
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 閉殻および開殻窒素活性種による複素環合成2018

    • Author(s)
      大江浩一
    • Organizer
      平成30年度有機合成化学北陸セミナー
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Iron-Catalyzed Radical Reactions Triggered by N-O Bond Cleavage of Oxime Esters2018

    • Author(s)
      T. Shimbayashi, K. Okamoto, K. Ohe
    • Organizer
      JGP Chem & ChemEn International Workshop: Sustainability-Oriented Organic Synthesis
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Book] Science of Synthesis Knowledge Updates, Vol. 2020/1, Section 4.4.40.722020

    • Author(s)
      Kazuhiro Okamoto and Kouichi Ohe
    • Total Pages
      158
    • Publisher
      Thieme
    • Related Report
      2020 Annual Research Report
  • [Book] Science of Synthesis Knowledge Updates2020

    • Author(s)
      K. Okamoto, K. Ohe
    • Total Pages
      159
    • Publisher
      Thieme Chemistry
    • Related Report
      2019 Annual Research Report
  • [Remarks] 京都大学工学研究科物質エネルギー化学専攻基礎物質化学講座基礎炭化水素化学分野 大江研究室

    • URL

      http://www.ehcc.kyoto-u.ac.jp/eh31/home/index-j.html

    • Related Report
      2020 Annual Research Report
  • [Remarks] 京都大学工学研究科物質エネルギー化学専攻基礎物質化学講座基礎炭化水素化学分野

    • URL

      http://www.ehcc.kyoto-u.ac.jp/eh31/home/index-j.html

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report

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Published: 2018-04-23   Modified: 2022-01-27  

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