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Development of rhenium-catalyzed carbon-carbon and carbon-heteroatom bonds

Research Project

Project/Area Number 18K05131
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionKansai University

Principal Investigator

Nishiyama Yutaka  関西大学, 化学生命工学部, 教授 (30180665)

Co-Investigator(Kenkyū-buntansha) 梅田 塁  関西大学, 化学生命工学部, 教授 (70467512)
Project Period (FY) 2018-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2020: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2019: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2018: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsレニウム / 触媒反応 / アルコール / π共役芳香族分子 / ジヒドロイソキノリン / イソキノリン / 多環式芳香族化合物 / 炭素 / 有機ケイ素化合物 / ヘテロ原子
Outline of Final Research Achievements

We have recently disclosed that rhenium complex, such as ReX(CO)5 (X = Br and Cl), serves as an air and moisture-tolerant catalyst for various organic reactions instead of various Lewis acid catalysts. In the continuation of the development of rhenium-catalyzed synthetic reactions, we investigated the new carbon-carbon and carbon-heteroatom bond formations used alcohols, esters, and ethers as the carbon sources in this research. In this research, we have found the rhenium complex acts as a useful catalyst on the carbon-carbon bond formations between alcohols and organosilicon compounds such as alkenyl and allyl silanes. We also found that rhenium catalyzed the deoxygenation and silylation of alcohols by hydrosilane.
In addition, we have shown that various polycyclic aromatic compounds, which were used as organic functional materials, were easily and efficiently synthesized by the use of rhenium complex catalyst.

Academic Significance and Societal Importance of the Research Achievements

本研究期間中に、安価かつ容易に入手可能なアルコールならびにアルコール誘導体を直接利用した、汎用性の高い多くの合成反応がレニウム錯体を用いることで触媒的に進行することを明らかにした。特に、アルコールならびにアルコール誘導体を用いため、従来法と比べ、副生成物の排出も少なく、原子効率の高い環境調和型合成反応が可能となった。また、レニウム錯体の特徴を利用することで、有機機能性材料への利用が期待される、種々のπ共役芳香族分子の効率的かつ簡便な合成が達成された。
以上のように。レニウム錯体特有の触媒反応を多く見出し、有機合成反応におけるレニウム触媒の有用性を明らかにした。

Report

(5 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Research-status Report
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (18 results)

All 2022 2021 2020 2019 2018 Other

All Journal Article (7 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 7 results) Presentation (10 results) (of which Int'l Joint Research: 3 results) Remarks (1 results)

  • [Journal Article] Rhenium complex-catalyzed deoxygenation and silylation of alcohols with hydrosilane2022

    • Author(s)
      Yutaka Nishiyama, Xu Shijie, Yuuki Hanatani, Susumu Tsuda, and Rui Umeda
    • Journal Title

      Tetrahedron Letters

      Volume: -

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective sunthesis of 1-halonaphthalenes by copper-catalyzed benzannulation2021

    • Author(s)
      Rui Umeda, Ryo Ueda, Taiki Tanaka, Akitsugu Hayashi, Masahiro Ikeshita, Shuichi Suzuki, Takeshi Naota, Yutaka Nishiyama
    • Journal Title

      Tetrahedron

      Volume: 79 Pages: 131872-131872

    • DOI

      10.1016/j.tet.2020.131872

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis and Physical Properties of π-Extended Molecules having p-Methylenequinone Unit2020

    • Author(s)
      Rui Umeda, Masamichi Nakatsukasa, Yutaka Nishiyama
    • Journal Title

      Heterocycles

      Volume: 101 Issue: 1 Pages: 318-327

    • DOI

      10.3987/com-19-s(f)12

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Nitroselenation of carbon-carbon triple bond by PhSeSePh and NO/O2 or NO22019

    • Author(s)
      Yutaka Nishiyama, Mari Sumuda, Noboru Sonoda
    • Journal Title

      Heteroatom Chemistry

      Volume: 29 Issue: 5-6

    • DOI

      10.1002/hc.21480

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Rhenium complex-catalyzed carbon-carbon formation of alcohols and organosilicon compounds2018

    • Author(s)
      Rui Umeda, Toshifumi Jikyo, Kazuki Toda, Issey Osaka, Yutaka Nishiyama
    • Journal Title

      Tetrahedron Letters

      Volume: 59 Issue: 12 Pages: 1121-1124

    • DOI

      10.1016/j.tetlet.2018.02.019

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 1,2-Dihydroisoquinolines via Rhenium-catalyzed Tandem Cyclization and Nucleophilic Addition of 2-(1-Alkyeny)arylaldimines2018

    • Author(s)
      Rui Umeda, Tetsuya Ishida, Yota Nakagawa, Mitsuru Inoue, Tatsuo Yajima, Yutaka Nishiyama
    • Journal Title

      Chemistry Letters

      Volume: 47 Issue: 6 Pages: 753-755

    • DOI

      10.1246/cl.180200

    • NAID

      130007384475

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Rhenium-catalyzed alpha-alkylation of enol acetates with alcohols or ethers2018

    • Author(s)
      Rui Umeda, Yuuki Takahashi, Takaaki Yamamoto, Hideki Iseki, Issey Osaka, Yutaka Nishiyama,
    • Journal Title

      Journal of Organometallic Chemistry

      Volume: 877 Pages: 92-101

    • DOI

      10.1016/j.jorganchem.2018.09.010

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] 鈴木-宮浦クロスカップリング反応を用いた [c2]daisy chain型ロタキサンの合成2022

    • Author(s)
      中村友哉、津田 進、藤原眞一、西山 豊
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 2つのオリゴフェニルアセチレン骨格を内包した[c2]daisy chain型ロタキサンの合成とその物性2022

    • Author(s)
      安村尚人、津田 進、藤原眞一、西山 豊
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] レニウム触媒存在下、2-Ethynylbenzaldimineの分子内閉環反応を利用したイソキノリン誘導体のone pot 合成2021

    • Author(s)
      八島弘樹、西山 豊、石田哲也
    • Organizer
      第50回複素環化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] レニウム触媒を用いた、2-Ethynylbenzaldimineからのイソキノリン誘導体のone pot合成2020

    • Author(s)
      八島弘樹、西山 豊、石田哲也
    • Organizer
      石油学会関西支部第29回、日本エネルギー学会関西支部第65回合同研究発表会
    • Related Report
      2020 Research-status Report
  • [Presentation] Kinetic Stabilization of Unstable Molecules by Highly Hindered π-System2019

    • Author(s)
      Rui Umeda and Yutaka Nishiyama
    • Organizer
      18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] サイズ選択的なナフチレンオリゴマーの合成2019

    • Author(s)
      安藤 翔生、能登 準也、梅田 塁、西山 豊
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] ピレン骨格を有する立体的に込み合った多置換ナフタレンの合成と物性2019

    • Author(s)
      津野 有輝、三木 悠平、角谷 翔太、梅田 塁、西山 豊
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] π拡張オキセピン誘導体の効率的合成2019

    • Author(s)
      橋本 勝慶、清水 祐児、猪田 裕太、梅田 塁、西山 豊
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] Synthesis and Photophysical Properties of Dicyanobisbenzodioxin2018

    • Author(s)
      Haruki Enomoto, Rui Umeda, and Yutaka Nishiyama
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-14)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Tetraarylethylene Derivatives by Benzannulation Reaction and Their Photophysical Properties2018

    • Author(s)
      Yuhei Miki, Rui Umeda, and Yutaka Nishiyama
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-14)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Remarks]

    • URL

      http://gakujo.kansai-u.ac.jp/profile/ja/gO0c810233e5da1a2)f895f0cece.html

    • Related Report
      2020 Research-status Report

URL: 

Published: 2018-04-23   Modified: 2023-01-30  

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