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Expansion of Frustration Revival Strategy

Research Project

Project/Area Number 18K14219
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

HOSHIMOTO Yoichi  大阪大学, 工学研究科, 准教授 (30710074)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywordsカルベン / ホスフィンイミド / 水素 / 触媒 / N-ヘテロ環状カルベン / ホスフィンオキシド / 二酸化炭素 / トリアリールホウ素 / ルイス酸 / ルイス塩基 / Frustrated Lewis Pairs / ホウ素
Outline of Final Research Achievements

This research project has developed a novel N-heterocyclic carbenes bearing a variety of N-phosphinimidoyl substituents. This substituents include an enantio-pure sufonyl group as well as amino-acid derivatives, which were rarely introduced in the reported carbene molecules. In additions, we successfully expanded our original frustration revival strategy by using PimIms.

Academic Significance and Societal Importance of the Research Achievements

本研究は反応性が高い化学種であるカルベンに、世界で初めてホスフィンイミド基を導入した。導入したホスフィンイミド基には、これまでに合成されてきたカルベン種には適用が困難であった光学活性なスルホニル基やアミノ酸誘導体が含まれる。これを活用し、研究者達が開発した、用途の乏しい酸-塩基付加体から高反応性化学種を再生する手法を拡張することに成功した。本研究により、薬や機能性材料を作る際の非金属触媒の設計に、新たな指針を加えることが可能となった。

Report

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

    (30 results)

All 2021 2020 2019 2018 Other

All Int'l Joint Research (2 results) Journal Article (10 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 10 results,  Open Access: 5 results) Presentation (18 results) (of which Int'l Joint Research: 3 results,  Invited: 2 results)

  • [Int'l Joint Research] アルバータ大学(カナダ)

    • Related Report
      2019 Research-status Report
  • [Int'l Joint Research] CSIR-CDRI(インド)

    • Related Report
      2019 Research-status Report
  • [Journal Article] Development of Metal Complexes Equipped with Structurally Flexible Carbenes2021

    • Author(s)
      Yoichi Hoshimoto * and Sensuke Ogoshi *
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 94 Issue: 1 Pages: 323-338

    • DOI

      10.1246/bcsj.20200293

    • NAID

      130007968755

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] N‐Phosphine Imide‐Substituted Imidazolylidenes (PimIms)2021

    • Author(s)
      Hoshimoto Yoichi、Nagai Shun、Hinogami Takaya、Hazra Sunit、Ogoshi Sensuke
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: - Issue: 5 Pages: 1085-1089

    • DOI

      10.1002/ajoc.202100109

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rotation-Triggered Transmetalation on a Heterobimetallic Cu/Al N-Phosphine-Oxide-Substituted Imidazolylidene Complex2020

    • Author(s)
      Asada, T. Hoshimoto, Y. Ogoshi, S.
    • Journal Title

      Journal of the American Chemical Society

      Volume: 142 Issue: 21 Pages: 9772-9784

    • DOI

      10.1021/jacs.0c03252

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Axial Chirality around N-P Bonds Induced by Complexation between E(C6F5)3 (E = B, Al) and an N-Phosphine Oxide-Substituted Imidazolinylidene: A Key Intermediate in the Catalytic Phosphinoylation of CO22020

    • Author(s)
      Asada Takahiro、Hoshimoto Yoichi、Kawakita Takahiro、Kinoshita Takuya、Ogoshi Sensuke
    • Journal Title

      The Journal of Organic Chemistry

      Volume: - Issue: 22 Pages: 14333-14341

    • DOI

      10.1021/acs.joc.9b03210

    • Related Report
      2020 Annual Research Report 2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Enantioselective Synthesis of Polycyclic γ-Lactams with Multiple Chiral Carbon Centers via Ni(0)-Catalyzed Asymmetric Carbonylative Cycloadditions without Stirring2020

    • Author(s)
      Ashida Keita、Hoshimoto Yoichi、Tohnai Norimitsu、Scott David E.、Ohashi Masato、Imaizumi Hanae、Tsuchiya Yuichiro、Ogoshi Sensuke
    • Journal Title

      Journal of the American Chemical Society

      Volume: 142 Issue: 3 Pages: 1594-1602

    • DOI

      10.1021/jacs.9b12493

    • Related Report
      2020 Annual Research Report 2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Ni(0)-Catalyzed Synthesis of Polycyclic α,β-Unsaturated γ-Lactams via Intramolecular Carbonylative Cycloaddition of Yne-imines with CO2020

    • Author(s)
      Keita Ashida, Yoichi Hoshimoto, Sensuke Ogoshi
    • Journal Title

      Synlett

      Volume: 31 Issue: 15 Pages: 1537-1541

    • DOI

      10.1055/s-0040-1707308

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Synthesis of Isoquinolines via Intramolecular Migration of N-Aryl Sulfonyl Groups on 1,5-Yne-Imines2020

    • Author(s)
      Hoshimoto Yoichi、Nishimura Chika、Sasaoka Yukari、Kumar Ravindra、Ogoshi Sensuke
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 93 Issue: 2 Pages: 182-186

    • DOI

      10.1246/bcsj.20190301

    • NAID

      130007798364

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Triarylborane-Catalyzed Reductive N-Alkylation of Amines: A Perspective2019

    • Author(s)
      Hoshimoto Yoichi、Ogoshi Sensuke
    • Journal Title

      ACS Catalysis

      Volume: 9 Issue: 6 Pages: 5439-5444

    • DOI

      10.1021/acscatal.9b01356

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Complexation between MOTf (M = Li and Na) and N-Phosphine Oxide-substituted Imidazolylidenes via Coordination of the N-Phosphoryl Groups2019

    • Author(s)
      Kinoshita Takuya、Sakuraba Mahiro、Hoshimoto Yoichi、Ogoshi Sensuke
    • Journal Title

      Chemistry Letters

      Volume: 48 Issue: 3 Pages: 230-233

    • DOI

      10.1246/cl.180930

    • NAID

      130007607701

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Main-Group-Catalyzed Reductive Alkylation of Multiply Substituted Amines with Aldehydes Using H22018

    • Author(s)
      Hoshimoto Yoichi、Kinoshita Takuya、Hazra Sunit、Ohashi Masato、Ogoshi Sensuke
    • Journal Title

      Journal of the American Chemical Society

      Volume: 140 Issue: 23 Pages: 7292-7300

    • DOI

      10.1021/jacs.8b03626

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] ホスフィンイミドを導入したN-テヘロ環状カルベンの合成2021

    • Author(s)
      長井駿、星本陽一、生越專介
    • Organizer
      日本化学会第101回春季年会(2021)
    • Related Report
      2020 Annual Research Report
  • [Presentation] 窒素上にホスフィンオキシドを有するN-ヘテロ環状カルベンを用いたニッケルカルボニル錯体の合成と反応性2021

    • Author(s)
      山内泰宏、川北崇裕、星本陽一、生越專介
    • Organizer
      日本化学会第101回春季年会(2021)
    • Related Report
      2020 Annual Research Report
  • [Presentation] 芳香族複素環化合物の水素化反応におけるトリアリールホウ素触媒のメタ位置換基効果2021

    • Author(s)
      橋本大輝、浅田貴大、星本陽一、生越專介
    • Organizer
      日本化学会第101回春季年会(2021)
    • Related Report
      2020 Annual Research Report
  • [Presentation] 有機ホウ素化合物を触媒とする含窒素環式化合物の連続的な水素化/脱水素化反応2020

    • Author(s)
      橋本大輝、浅田貴大、星本陽一、生越專介
    • Organizer
      第10回CSJ化学フェスタ2020
    • Related Report
      2020 Annual Research Report
  • [Presentation] ホスフィンイミドを有するN-ヘテロ環状カルベンの開発と反応性に関する研究2020

    • Author(s)
      長井駿、日野上貴哉、星本陽一、生越專介
    • Organizer
      第10回CSJ化学フェスタ2020
    • Related Report
      2020 Annual Research Report
  • [Presentation] 含窒素環式化合物の触媒的水素化/脱水素化反応を利用した水素精製2020

    • Author(s)
      橋本大輝、浅田貴大、星本陽一、生越專介
    • Organizer
      第9回JACI/GSCシンポジウム
    • Related Report
      2020 Annual Research Report
  • [Presentation] ホスフィノイル基をN上に導入した環状へテロカルベンの合成と利用2019

    • Author(s)
      星本陽一、生越專介
    • Organizer
      創造機能化学第116委員会
    • Related Report
      2019 Research-status Report
  • [Presentation] 窒素上にホスフィンオキシドを導入したN-ヘテロ環状カルベン を配位子とするW(0)錯体の合成とその反応性2019

    • Author(s)
      川北崇裕、星本陽一、生越專介
    • Organizer
      第52回有機金属若手の会 夏の学校
    • Related Report
      2019 Research-status Report
  • [Presentation] PoxIm とASB。ざっくりとしたアイデアに本気で向かい合ってみた結果。2019

    • Author(s)
      星本陽一
    • Organizer
      応用化学セミナーミニシンポジウム
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] 多機能多用途カルベンの活用2019

    • Author(s)
      星本陽一
    • Organizer
      第1回機能分子化学若手シンポジウム
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] Phosphorylation of carbon-oxygen bond mediated by N-phosphine oxide-substituted imidazolylidenes2019

    • Author(s)
      Takahiro Asada, Yoichi Hoshimoto, Sensuke Ogoshi
    • Organizer
      ACS Fall 2019 National Meeting & Exposition
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Complexation between Al(C6F5)3 and N-Phoshpnine Oxide-Substituted Imidazolidenes2019

    • Author(s)
      Takahiro Asada, Yoichi Hoshimoto, Sensuke Ogoshi
    • Organizer
      27th International Society of Heterocyclic Chemistry Congress(ISHC)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] 窒素上にホスフィンオキシドを導入したN-ヘテロ環状カルベンを配位子とするW(0)錯体の合成と反応性2019

    • Author(s)
      川北崇裕、星本陽一、生越專介
    • Organizer
      第66回有機金属化学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] 窒素上にホスフィンオキシドを導入したN-ヘテロ環状カルベンを配位子とするNi(0)カルボニル錯体の合成2019

    • Author(s)
      川北崇裕、星本陽一、生越専介
    • Organizer
      第9回CSJ化学フェスタ2019
    • Related Report
      2019 Research-status Report
  • [Presentation] 有機分子触媒を用いた1,5-イン-イミンからのN-ス ルホニル基転位を経由するイソキノリンの合成2019

    • Author(s)
      西村知華、星本陽一、生越専介
    • Organizer
      第9回CSJ化学フェスタ2019
    • Related Report
      2019 Research-status Report
  • [Presentation] 窒素上にホスフィンオキシドを導入したN-ヘテロ環状カルベンを配位子とするW(0) カルボニル錯体のルイス酸に対する反応性2019

    • Author(s)
      川北崇裕、星本陽一、生越專介
    • Organizer
      第46回有機典型元素化学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] 窒素上にホスフィンオキシドを導入したNーヘテロ環状カルベンと典型元素または遷移金属から成る錯体の合成および反応性2018

    • Author(s)
      木下拓也、櫻羽真煕、大保政貴、Manussada Ratanasak、星本陽一、長谷川淳也、生越專介
    • Organizer
      第45回有機典型元素化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] Synthesis and Reactivity of Metal Complexes Bearing N-Phosphine Oxide-Substituted Imidazolylidenes2018

    • Author(s)
      Yoichi Hoshimoto, Yasuhiro Yamauchi, Takuya Kinoshita, Sensuke Ogoshi
    • Organizer
      XXVIII International Conference on Organometallic Chemistry
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research

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Published: 2018-04-23   Modified: 2023-03-23  

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