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Development of Coupling Reactions between Enol Ethers with Metal Enolates via Characteristic Lewis Acids

Research Project

Project/Area Number 24750090
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(系)研究科(研究院), 助教 (30550115)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2013: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Fiscal Year 2012: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords有機合成化学 / 有機金属化学 / カップリング反応 / エノールエーテル
Outline of Final Research Achievements

The coupling reaction between enol ethers and silyl ketene acetals in the presence of gallium tribromide catalyst. In this reaction system, various types of enol ethers and silyl ketene acetals were applicable. As far as enol ethers, not only vinyl ethers but also substituted alkenyl ethers were found to be suitable substrates. The scope of silyl ketene acetals was also wide so that diallkyl-, diaryl-, and alkylarylsubstituted ones afforded the corresponding products in high yields. The observation of the reaction intermediate and kinetic study revealed that the coupling reaction proceeds via carbogallation among gallium tribromide, an enol ether, and a silyl ketene acetal.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (30 results)

All 2015 2014 2013 2012

All Journal Article (12 results) (of which Peer Reviewed: 12 results,  Acknowledgement Compliant: 1 results) Presentation (18 results) (of which Invited: 1 results)

  • [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 Annual Research 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 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Indium Triiodide Catalyzed Reductive Functionalization of Amides via the Single-Stage Treatment of Hydrosilanes and Organosilicon Nucleophiles2013

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

      Org. Lett.

      Volume: 15 Issue: 13 Pages: 3452-3455

    • DOI

      10.1021/ol4015317

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Alkylbismuths by Regiodivergent Carbobismuthination of Simple Alkenes2013

    • Author(s)
      Yoshihiro Nishimoto, Midori Takeuchi, Makoto Yasuda, Akio Baba
    • Journal Title

      Chem. Eur. J.

      Volume: 19 Issue: 43 Pages: 14411-14415

    • DOI

      10.1002/chem.201302194

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Syntheses of Aldol Products and Cyanohydrins from Carboxylic Acids Using Hydrosilanes, Organosilicon Reagents, and Indium Triiodide Catalyst2013

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

      Chemistry Letters

      Volume: 42 Issue: 12 Pages: 1551-1553

    • DOI

      10.1246/cl.130790

    • NAID

      130004867849

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Direct Use of Esters in the Mukaiyama Aldol Reaction: A Powerful and Convenient Alternative to Aldehydes2012

    • Author(s)
      Inamoto, Y.
    • Journal Title

      Org. Lett.

      Volume: 14 Issue: 4 Pages: 1168-1171

    • DOI

      10.1021/ol3001443

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Regio- and Stereoselective Carbobismuthination of Alkynes2012

    • Author(s)
      西本能弘
    • Journal Title

      Angew.Chem.Int.Ed.

      Volume: 51 Issue: 4 Pages: 1051-1054

    • DOI

      10.1002/anie.201107127

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of a Wide Range of Thioethers by Indium Triiodide Catalyzed Direct Coupling between Alkyl Acetates and Thiosilanes2012

    • Author(s)
      Nishimoto, Y.; Okita, A.; Yasuda, M.; Baba, A
    • Journal Title

      Org. Lett

      Volume: 14 Issue: 7 Pages: 1846-1849

    • DOI

      10.1021/ol300450j

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Dependence of catalytic properties of indium-implanted SiO_2 thin films on the energy and dose of incident indium ions2012

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

      Thin Solid Films

      Volume: 520 Issue: 15 Pages: 4894-4897

    • DOI

      10.1016/j.tsf.2012.03.028

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Low Energy Metal Ion Beam Production with a Modified Freeman-Type Ion Source for Development of Novel Catalysts2012

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

      e-Journal of Surface Science and Nanotechnology

      Volume: 10 Issue: 0 Pages: 139-144

    • DOI

      10.1380/ejssnt.2012.139

    • NAID

      130004438798

    • ISSN
      1348-0391
    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Gallium Tribromide Catalyzed Coupling Reaction of Alkenyl Ethers with Ketene Silyl Acetals2012

    • Author(s)
      Nishimoto, Y.; Ueda, H.; Yasuda, M.; Baba, A
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 51 Issue: 32 Pages: 8073-8076

    • DOI

      10.1002/anie.201203778

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] InCl_3/Me_3SiCl-Catalyzed Direct Michael Addition of Enol Acetates to α,β-Unsaturated Ketones2012

    • Author(s)
      大西祥晴・米田勇樹・西本能弘・安田 誠・馬場章夫
    • Journal Title

      Organic Letter

      Volume: 14 Issue: 22 Pages: 5788-5791

    • DOI

      10.1021/ol302888k

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [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 Annual Research 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 Annual Research 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
      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 Annual Research 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
      大阪大学(大阪府豊中市)
    • Year and Date
      2014-10-09 – 2014-10-10
    • Related Report
      2014 Annual Research 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 Annual Research 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 Annual Research 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 Annual Research Report
  • [Presentation] Coupling Reactions of Enol Ethers with Ketene Silyl Acetals and Silyl Ketene Imines Catalyzed by Group 13 Lewis Acids2014

    • Author(s)
      Yoshihiro Nishimoto
    • Organizer
      COMC 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 Annual Research Report
    • Invited
  • [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
      ロイトン札幌(北海道札幌市)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] Three-component Reaction of Esters with Silyl Cyanide and Ketene Silyl Acetals Catalyzed by Gallium Trihalides2014

    • Author(s)
      Yoshihiro Inamoto, Yuta Kaga, Yoshihiro Nishimoto, Makoto Yasuda, Akio Baba
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis of Alkylbismuths by Carbobismuthination of Alkenes and Its Application to Reaction Integration2013

    • Author(s)
      Yoshihiro Nishimoto, Midori Takeuchi, Makoto Yasuda, and Akio Baba
    • Organizer
      第8回集積有機合成国際シンポジウム
    • Place of Presentation
      東大寺総合文化センター
    • Related Report
      2013 Research-status Report
  • [Presentation] Gallium Tribromide-Catalyzed Coupling Reaction of Enol Derivatives with Ketene Silyl Acetals2013

    • Author(s)
      Yoshihiro Nishimoto, Hiroki Ueda, Hiroto Imaoka, Makoto Yasuda, Akio Baba
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Direct Introduction of Two Kinds of Carbon Nucleophiles into Esters Using Organosilicon Reagents and Lewis Acid Catalyst2013

    • Author(s)
      Yoshihiro Inamoto, Yuta Kaga, Yoshihiro Nishimoto, Makoto Yasuda, Akio Baba
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Research-status Report
  • [Presentation] ヨウ化インジウム触媒によるヒドロシランと有機ケイ素求核剤を用いたアミドの多置換アミンへの直接変換反応2013

    • Author(s)
      稲本 佳寛・加賀 悠太・西本 能弘・安田 誠・馬場 章夫
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学 びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] インジウム触媒と有機ケイ素化合物を利用したカルボン酸から第二級アルコールへの変換反応2013

    • Author(s)
      稲本 佳寛・西本 能弘・安田 誠・馬場 章夫
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学 びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] ヨウ化インジウムを用いたアレニルエーテルとケテンシリルアセタールのカップリング反応2013

    • Author(s)
      西村 貴至・西本 能弘・安田 誠・馬場 章夫
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学 びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] 臭化ガリウム触媒によるケテンシリルアセタールとアルケニルエーテル類とのカップリング反応2013

    • Author(s)
      西本 能弘・上田 博紀・今岡 洋人・安田 誠・馬場 章夫
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学 びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] 臭化ビスマスとケテンシリルアセタールによる アルキンの位置および立体選択的カルボビスマス化2012

    • Author(s)
      西本 能弘・竹内 翠・安田 誠・馬場 章 夫
    • Organizer
      第 59 回 有機金属化学討論会
    • Place of Presentation
      大阪大学吹田キャンパス
    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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