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Development of Coupling Reaction of Enol Derivatives as Electrophiles Using Well-Controlled Lewis Acids

Research Project

Project/Area Number 26810059
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionOsaka University

Principal Investigator

Nishimoto Yoshihiro  大阪大学, 工学研究科, 助教 (30550115)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2014: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsカップリング反応 / ルイス酸 / 有機合成化学
Outline of Final Research Achievements

A cross-coupling reaction is one of the most important method for carbon-carbon bond formation. Generally, organic halides are used as electrophiles due to high reactivity, but they are expensive and potentially toxic. In contrast, oxygen-based electrophiles such as alcohol-, arenol-, enol-derivatives have attracted much attention. These compounds have several advantages over organic halides. However, this type of coupling reaction is very difficult because of the inert carbon-oxygen bond. I have established coupling reactions using enol ethers with ketene silyl acetals catalyzed by gallium bromide. And, the coupling with silyl ketene imines was also achieved. Both coupling reactions proceed via addition-elimination mechanism involving region- and stereoselective carbometalation.
Various types of enol derivatives, ketene silyl acetals, and silyl ketene imines were applicable.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (35 results)

All 2017 2016 2015 2014

All Journal Article (7 results) (of which Peer Reviewed: 7 results,  Acknowledgement Compliant: 6 results,  Open Access: 1 results) Presentation (28 results) (of which Int'l Joint Research: 5 results)

  • [Journal Article] Coupling Reaction of Enol Derivatives with Silyl Ketene Acetals Catalyzed by Gallium Trihalides2016

    • Author(s)
      Yoshihiro Nishimoto, Yuji Kita, Hiroki Ueda, Hiroto Imaoka, Kouji Chiba, Makoto Yasuda, and Akio Baba
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 33 Pages: 11837-11845

    • DOI

      10.1002/chem.201602150

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Thioethers by InI3-Catalyzed Substitution of Siloxy Group Using Thiosilanes2016

    • Author(s)
      Yoshihiro Nishimoto, Aya Okita, Akio Baba, Makoto Yasuda
    • Journal Title

      Molecules

      Volume: 21 Issue: 10 Pages: 1330-1336

    • DOI

      10.3390/molecules21101330

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Synthesis of 1,4-Dicarbonyl Compounds from Silyl Enol Ethers and Bromocarbonyls, Catalyzed by an Organic Dye under Visible Light Irradiation with Perfect Selectivity for the Halide Moiety over the Carbonyl Group2016

    • Author(s)
      Naoto Esumi, Kensuke Suzuki, Yoshihiro Nishimoto, and Makoto Yasuda
    • Journal Title

      Org. Lett.

      Volume: 18 Issue: 21 Pages: 5704-5707

    • DOI

      10.1021/acs.orglett.6b02869

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Indium Tribromide Catalyzed Coupling Reaction of Enol Ethers with Silyl Ketene Imines toward Synthesis of ß,γ-Unsaturated Nitriles2015

    • Author(s)
      Yoshihiro Nishimoto, Takashi Nishimura, Makoto Yasuda
    • Journal Title

      Chem. Eur. J.

      Volume: 21 Issue: 50 Pages: 18301-18308

    • DOI

      10.1002/chem.201503414

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Indium implantation onto zeolite by pulse arc plasma process for the development of novel catalysts2015

    • Author(s)
      S. Yoshimura, Y. Nishimoto, M. Kiuchi, M. Yasuda
    • Journal Title

      Chemistry Letters

      Volume: 44 Issue: 10 Pages: 1292-1294

    • DOI

      10.1246/cl.150499

    • NAID

      130005101464

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Gallium Trihalide Catalyzed Sequential Addition of Two Different Carbon Nucleophiles to Esters by Using Silyl Cyanide and Ketene Silyl Acetals2014

    • Author(s)
      Yoshihiro Inamoto, Yuta Kaga, Yoshihiro Nishimoto, Makoto Yasuda, Akio Baba
    • Journal Title

      Chemistry - A European Journal

      Volume: 37 Issue: 37 Pages: 11664-11668

    • DOI

      10.1002/chem.201403734

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Indium Chloride Catalyzed Alkylative Rearrangement of Propargylic Acetates Using Alkyl Chlorides, Alcohols, and Acetates: Facile Synthesis of α-Alkyl-α,β-Unsaturated Carbonyl Compounds2014

    • Author(s)
      Yoshiharu Onishi, Yoshihiro Nishimoto, Makoto Yasuda, Akio Baba
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 4 Pages: 1176-1179

    • DOI

      10.1021/ol500046e

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Presentation] サマリウムトリフラート・スズアルコキシド協働触媒によるα-アルコキシケトンの不飽和ケトン類への高ジアステレオ選択的直接マイケル付加2017

    • Author(s)
      江住直人、西本能弘、安田誠
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthesis of Isocoumarin by Intramolecular Oxyindation of Alkynes with Indium Triiodide2017

    • Author(s)
      喜多悠二、西本能弘、安田誠
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学
    • Related Report
      2016 Annual Research Report
  • [Presentation] イノールエーテルへの位置および立体選択的なカルボジンケーションを利用したβ-アリーロキシアルケニル亜鉛種の合成2017

    • Author(s)
      西本能弘、カン ギョンミン、安田誠
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学
    • Related Report
      2016 Annual Research Report
  • [Presentation] トリアリールビスマスを用いた1,2-ジアミンの酸化的開裂反応2017

    • Author(s)
      西本能弘、中尾秀一、安田誠
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学
    • Related Report
      2016 Annual Research Report
  • [Presentation] アルミニウム塩を直接用いたアルキンへのアンチ付加型カルボアルミニウム化2017

    • Author(s)
      西本能弘、平瀬璃奈、安田誠
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学
    • Related Report
      2016 Annual Research Report
  • [Presentation] 有機色素光触媒を用いたシリルエノールエーテルとα-ブロモカルボニル化合物の選択的ハライド置換反応による1,4-ジカルボニル化合物の合成2017

    • Author(s)
      江住直人、鈴木健介、西本能弘、安田誠
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学
    • Related Report
      2016 Annual Research Report
  • [Presentation] 中程度のルイス酸性と高いπ電子親和性を兼ね備えた高周期典型金属を活用したカルボメタル化2017

    • Author(s)
      西本能弘
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学
    • Related Report
      2016 Annual Research Report
  • [Presentation] インジウム塩を用いた炭素炭素多重結合のオキシメタル化とその応用2016

    • Author(s)
      喜多悠二、西本能弘、安田誠
    • Organizer
      第63回有機金属化学討論会
    • Place of Presentation
      早稲田大学
    • Related Report
      2016 Annual Research Report
  • [Presentation] 亜鉛塩によるイノールエーテルへのカルボジンク化を鍵としたβ―アルコキシアルケニル亜鉛種の合成2016

    • Author(s)
      西本能弘、カン ギョンミン、安田誠
    • Organizer
      第63回有機金属化学討論会
    • Place of Presentation
      早稲田大学
    • Related Report
      2016 Annual Research Report
  • [Presentation] Development of cross-coupling reaction between enol derivatives and silyl ketene acetals catalyzed by gallium trihalides2015

    • Author(s)
      Yoshihiro Nishimoto, Yuji Kita, Makoto Yasuda, Akio Baba
    • Organizer
      Pacifichem 2015 meeting
    • Place of Presentation
      ホノルル、ハワイ、アメリカ
    • Year and Date
      2015-12-17
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis of organobismuth compounds by carbobismuthination of alkynes and alkenes using bismuth trihalides and ketene silyl acetals2015

    • Author(s)
      Yoshihiro Nishimoto, Midori Takeuchi, Makoto Yasuda, Akio Baba
    • Organizer
      Pacifichem 2015 meeting
    • Place of Presentation
      ホノルル、ハワイ、アメリカ
    • Year and Date
      2015-12-17
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Regio- and stereoselective carboindation of ynol ethers using indium tribromide and silyl enolates2015

    • Author(s)
      Kang Kyoungmin, Yoshihiro Nishimoto, Makoto Yasuda
    • Organizer
      Pacifichem 2015 meeting
    • Place of Presentation
      ホノルル、ハワイ、アメリカ
    • Year and Date
      2015-12-17
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Development and Mechanistic Investigation of Cross-Coupling Reaction between Enol Derivatives and Silyl Ketene Acetals Catalyzed by Gallium Trihalides2015

    • Author(s)
      NiShimoto Yoshihiro, Kita Yuji, Yasuda Makoto
    • Organizer
      The Thirteenth International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-13)
    • Place of Presentation
      Rihga Royal Hotel, Kyoto, Japan
    • Year and Date
      2015-11-10
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] nBr3/Me3SiBr-Catalyzed Coupling Reaction of Enol Ethers with Silyl Ketene Imines2015

    • Author(s)
      Yoshihiro Nishimoto, Takashi Nishimura, Makoto Yasuda
    • Organizer
      The Thirteenth International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-13)
    • Place of Presentation
      Rihga Royal Hotel, Kyoto, Japan
    • Year and Date
      2015-11-10
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 臭化ガリウムが触媒するエノール誘導体とシリルケテンアセタールのクロスカップリング反応の機構解明2015

    • Author(s)
      西本能弘、喜多悠二、安田誠
    • Organizer
      第5回CSJ化学フェスタ
    • Place of Presentation
      東京都江戸川区タワーホール船堀
    • Year and Date
      2015-10-13
    • Related Report
      2015 Research-status Report
  • [Presentation] 臭化インジウム触媒による電子不足エノールエーテルとケイ素エノラートのカップリング反応2015

    • Author(s)
      西本 能弘、飛鷹 富美子、安田 誠
    • Organizer
      第5回CSJ化学フェスタ
    • Place of Presentation
      東京都江戸川区タワーホール船堀
    • Year and Date
      2015-10-13
    • Related Report
      2015 Research-status Report
  • [Presentation] Indium Tribromide Catalyzed Coupling Reaction of Enol Ethers with Silyl Ketene Imines Using Bromotrimethylsilane as Co-catalyst2015

    • Author(s)
      Yoshihiro Nishimoto, Takashi Nishimura, Makoto Yasuda, and Akio Baba
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学
    • Year and Date
      2015-09-08
    • Related Report
      2015 Research-status Report
  • [Presentation] 立体および位置選択的イノールエーテルのカルボインジウム化2015

    • Author(s)
      Kang Kyoungmin, 西本 能弘, 安田 誠
    • Organizer
      第35回有機合成若手セミナー「明日の有機合成を担う人のために」
    • Place of Presentation
      京都府立大学
    • Year and Date
      2015-08-01
    • Related Report
      2015 Research-status Report
  • [Presentation] InBr3触媒による電子不足エノールエーテルとケイ素エノラートのカップリング反応2015

    • Author(s)
      西本 能弘、飛鷹 富美子、安田 誠
    • Organizer
      第35回有機合成若手セミナー「明日の有機合成を担う人のために」
    • Place of Presentation
      京都府立大学
    • Year and Date
      2015-08-01
    • Related Report
      2015 Research-status Report
  • [Presentation] 複素環を骨格に導入したかご型ホウ素錯体の光によるルイス酸性制御2015

    • Author(s)
      安永 亮佑・西本 能弘・安田 誠
    • Organizer
      日本化学会代95春季年会
    • Place of Presentation
      日本大学(千葉県船橋市)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Research-status Report
  • [Presentation] エノール誘導体とシリルケテンアセタールの臭化ガリウム触媒カップリングの反応機構解明2015

    • Author(s)
      西本 能弘・喜多 悠二・安田 誠・馬場 章夫
    • Organizer
      日本化学会代95春季年会
    • Place of Presentation
      日本大学(千葉県船橋市)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Research-status Report
  • [Presentation] Development of GaBr3-Catalyzed Cross Coupling Using Enol Derivatives as Alkenyl Electrophiles2014

    • Author(s)
      Yoshihiro Nishimoto, Yuji Kita, Makoto Yasuda, Akio Baba
    • Organizer
      The 2nd International Conference on Organometallics and Catalysis
    • Place of Presentation
      奈良市東大寺総合文化センター(奈良県奈良市)
    • Year and Date
      2014-10-26 – 2014-10-29
    • Related Report
      2014 Research-status Report
  • [Presentation] GaBr3-Catalyzed Cross-Coupling Reaction between Enol Derivatives and Ketene Silyl Acetals via Carbogallation2014

    • Author(s)
      Yoshihiro Nishimoto, Yuji Kita, Makoto Yasuda, Akio Baba
    • Organizer
      ETH Zurich-Osaka Univ. Joint Symposium
    • Place of Presentation
      日本大学(千葉県船橋市)
    • Year and Date
      2014-10-09
    • Related Report
      2014 Research-status Report
  • [Presentation] 臭化ガリウム触媒を用いるエノール誘導体とケテンシリルアセタールのカップリング反応の展開と機構解明2014

    • Author(s)
      西本能弘・喜多悠二・安田 誠・馬場章夫
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学(福岡県福岡市)
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Research-status Report
  • [Presentation] 配位子修飾によるかご型錯体の芳香族選択性制御2014

    • Author(s)
      丸山 輝・安永亮佑・西本能弘・安田 誠・馬場章夫
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学(宮城県仙台市)
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Research-status Report
  • [Presentation] 複素環導入によるかご型ホウ素錯体のルイス酸性の精密制御2014

    • Author(s)
      安永 亮佑・西本 能弘・安田 誠・馬場章夫
    • Organizer
      第34回有機合成若手セミナー 明日の有機合成を担う人のために
    • Place of Presentation
      大阪大学(大阪府豊中市)
    • Year and Date
      2014-08-05
    • Related Report
      2014 Research-status Report
  • [Presentation] Coupling Reactions of Enol Ethers with Ketene Silyl Acetals and Silyl Ketene Imines Catalyzed by Group 13 Lewis Acids2014

    • Author(s)
      西本 能弘
    • Organizer
      ICOMC 2014 Post-Symposium in Osaka: New Aspects on Reactive Organometallic Complexes of Transition Metals
    • Place of Presentation
      大阪大学(大阪府吹田市)
    • Year and Date
      2014-07-19
    • Related Report
      2014 Research-status Report
  • [Presentation] Carbobismuthination of Carbon-Carbon Multiple Bonds by Using Bismuth Trihalides and Ketene Silyl Acetals2014

    • Author(s)
      西本能弘・竹内 翠・安田 誠・馬場章夫
    • Organizer
      The XXXVI International Conference on Organometallic Chemistry
    • Place of Presentation
      北海道札幌市 ロイトン札幌
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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