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Development of Organic Main-group Metal Catalysts by Expansion of Vacant Orbitals

Research Project

Project/Area Number 16K05719
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Inorganic chemistry
Research InstitutionOsaka University

Principal Investigator

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

Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2018: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2017: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2016: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Keywords触媒開発 / 有機合成反応 / ルイス酸触媒 / 有機金属化合物 / アルミニウム / 有機化学
Outline of Final Research Achievements

In this study, Pheox- and Phebox-Al complexes stabilized by intramolecular coordination were synthesized and their Lewis acidic properties were controlled by hydrocarbyl ligands. The exchange of counter anions also succeeded in the expression of higher Lewis acidity. It is noteworthy that when the synthesized aluminum complex was applied to catalysis, it showed high activity in the hydroboration reaction of aldehydes and functioned as a more efficient catalyst than typical aluminum chloride and the like.

Academic Significance and Societal Importance of the Research Achievements

金属触媒は現代の化学において、重要な役割を担っている。遷移金属触媒は多機能および高活性金属錯体が多く開発されており、医薬品、機能性高分子、有機電子材料などの精密化成品の合成に欠かせない存在である。しかし、遷移金属の多くは希少で、資源の枯渇が危惧されている。一方で、典型金属は豊富で安価であるために、遷移金属触媒の代わりに典型金属触媒を利用できれば、元素戦略の観点からもその意義は大きい。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (40 results)

All 2019 2018 2017 2016

All Journal Article (12 results) (of which Peer Reviewed: 12 results,  Open Access: 2 results,  Acknowledgement Compliant: 3 results) Presentation (27 results) (of which Int'l Joint Research: 3 results,  Invited: 2 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Regio- and Stereoselective Allylindation of Alkynes Using InBr3 and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes2018

    • Author(s)
      Yoshihiro Nishimoto, Junyi Yi, Tatsuaki Takata, Akio Baba, and Makoto Yasuda
    • Journal Title

      Molecules

      Volume: 23 Issue: 8 Pages: 1884-1897

    • DOI

      10.3390/molecules23081884

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Selective Oxymetalation of Terminal Alkynes via 6-Endo Cyclization: Mechanistic Investigation and Application to the Efficient Synthesis of 4-Substituted Isocoumarins2018

    • Author(s)
      Yuji Kita, Tetsuji Yata, Yoshihiro Nishimoto, Kouji Chiba, and Makoto Yasuda
    • Journal Title

      Chem. Sci.

      Volume: 9 Issue: 28 Pages: 6041-6052

    • DOI

      10.1039/c8sc01537f

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Anti-Carboalumination of Alkynes Using Aluminum Trihalide and Silyl Ketene Imines: Stereo- and Regioselective Synthesis of Alkenylaluminum Compounds Bearing a Cyano Group2018

    • Author(s)
      Yoshihiro Nishimoto, Rina Hirase, and Makoto Yasuda
    • Journal Title

      Org. Lett.

      Volume: 20 Issue: 12 Pages: 3651-3655

    • DOI

      10.1021/acs.orglett.8b01371

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Regio- and Stereo-controlled Addition Reaction of Aminoallylic Stannanes to Aldehydes Mediated by Germanium Dichloride2018

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

      Chem. Lett.

      Volume: 47 Issue: 7 Pages: 821-824

    • DOI

      10.1246/cl.180291

    • NAID

      130007402813

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Deposition of Indium Nanoparticles on Powdered Material by Pulse Arc Plasma to Synthesize Catalysts for Friedel-Crafts Alkylation2018

    • Author(s)
      Yoshimura Satoru、Nishimoto Yoshihiro、Sugimoto Satoshi、Kiuchi Masato、Yasuda Makoto
    • Journal Title

      e-Journal of Surface Science and Nanotechnology

      Volume: 16 Issue: 0 Pages: 105-110

    • DOI

      10.1380/ejssnt.2018.105

    • NAID

      130006727036

    • ISSN
      1348-0391
    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Indium Catalyzed Hydrofunctionalization of Styrene Derivatives Bearing a Hydroxy Group with Organosilicon Nucleophiles2018

    • Author(s)
      Yuji Kita, Tetsuji Yata, Yoshihiro Nishimoto, and Makoto Yasuda
    • Journal Title

      J. Org. Chem.

      Volume: 83 Issue: 2 Pages: 740-753

    • DOI

      10.1021/acs.joc.7b02739

    • Related Report
      2018 Annual Research Report 2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Generation of α-Iminyl Radicals from α-Bromo Cyclic N-Sulfonylimines and Application to Coupling with Various Radical Acceptors Using a Photoredox Catalyst2017

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

      Chem. Eur. J.

      Volume: 24 Issue: 2 Pages: 312-316

    • DOI

      10.1002/chem.201704060

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Regio- and Stereoselective Anti-Carbozincation of Alkynyl Ethers Using ZnBr2 toward (Z)-β-Zincated Enol Ether Synthesis2017

    • Author(s)
      Nishimoto Yoshihiro、Kang Kyoungmin、Yasuda Makoto
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 14 Pages: 3927-3930

    • DOI

      10.1021/acs.orglett.7b01847

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] First anti-Selective Direct Michael Addition of α-Alkoxy Ketones to Enones by Cooperative Catalysis of Samarium(III) Trifluoromethanesulfonate and Tributyltin Methoxide2017

    • Author(s)
      Esumi Naoto、Nishimoto Yoshihiro、Yasuda Makoto
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2017 Issue: 19 Pages: 2831-2835

    • DOI

      10.1002/ejoc.201700501

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [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 Research-status 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 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [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 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] PheoxおよびPhebox配位子を有する有機アルミニウム錯体の合成とルイス酸触媒反応への応用2019

    • Author(s)
      中尾秀一, 西本能弘, 安田 誠
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 臭化インジウムと有機ケイ素求核剤を用いたイナミドへのカルボインジウム化によるアミノアルケニルインジウムの位置および立体選択的合成2019

    • Author(s)
      カン ギョンミン, 坂本宏介, 西本能弘, 安田 誠
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Synthesis, Luminescence Properties, and Synthetic Application of Multi-Substituted 2-Pyrones Including a Carbon-Indium Bond2019

    • Author(s)
      矢田哲治, 喜多悠二, 西本能弘, 安田 誠
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Cross-Coupling Reaction of Enol Derivatives with Silyl Ketene Acetals or Silyl Ketene Imines2018

    • Author(s)
      西本 能弘
    • Organizer
      The 13th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-13))
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] α-アミノアリルスズを用いたラジカルアリル化によるE体選択的エナミド合成2018

    • Author(s)
      鈴木健介, 西本能弘, 安田 誠
    • Organizer
      第65回有機金属化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] オキシインジウム化を鍵としたα-ピロン骨格を有する有機インジウム化合物の合成とその応用2018

    • Author(s)
      喜多悠二, 矢田哲治, 西本能弘, 安田 誠
    • Organizer
      第65回有機金属化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 3位に炭素-金属結合を有する2,4,6-トリアリールピリリウム類の選択的合成2018

    • Author(s)
      喜多悠二, 西本能弘, 安田 誠
    • Organizer
      第48回複素環化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] オキシインジウム化を鍵とした炭素-金属結合を有するα-ピロンの合成と応用2018

    • Author(s)
      矢田哲治, 喜多悠二, 西本能弘, 安田 誠
    • Organizer
      第48回複素環化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 含窒素アリルスズを用いたラジカル開始剤によるE体選択的エナミド合成2018

    • Author(s)
      鈴木健介, 西本能弘, 安田 誠
    • Organizer
      第7回CSJ化学フェスタ
    • Related Report
      2018 Annual Research Report
  • [Presentation] 臭化インジウムと有機ケイ素求核剤を用いたイナミドへのアンチ付加型カルボメタル化2018

    • Author(s)
      カン ギョンミン, 坂本宏介, 西本能弘, 安田 誠
    • Organizer
      第45回有機典型元素化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Synthesis of C,N-Chelated Organoaluminum Complexes and Application to Lewis Acid Catalyst2018

    • Author(s)
      中尾秀一, 西本能弘, 安田 誠
    • Organizer
      IKCOC-14
    • Related Report
      2018 Annual Research Report
  • [Presentation] Lewis 酸-Lewis 塩基触媒を指向した13 族金属Pheox 錯体の合成2018

    • Author(s)
      西本 能弘、大下倉 太朗、安田 誠
    • Organizer
      日本化学会代98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 分子内オキシメタル化による炭素ーインジウム結合を有するピリリウム誘導体の合成2018

    • Author(s)
      喜多悠二, 西本能弘, 安田 誠
    • Organizer
      日本化学会代98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] PheoxおよびPhebox配位子を有する有機アルミニウム錯体の合成とβ-アルコキシエノンとシリルエノラートとのカップリング反応への応用2018

    • Author(s)
      中尾秀一, 西本能弘, 安田 誠
    • Organizer
      日本化学会代98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] Cross-Coupling Reaction of Enol Derivatives with Silyl Ketene Acetals or Silyl Ketene Imines2017

    • Author(s)
      西本能弘
    • Organizer
      ISPAC 2017
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis of Isocoumarins by Intramolecular Oxyindation of Alkynes2017

    • Author(s)
      喜多悠二, 西本能弘, 安田 誠
    • Organizer
      ISPAC 2017
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] 新規有機アルミニウム錯体の合成とエノールエーテルとシリルエノラートのカップリング反応への応用2017

    • Author(s)
      西本能弘、中尾秀一、町中翔太、安田誠
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] インジウム塩を用いたアルキンの位置選択的分子内オキシメタル化を鍵としたイソクマリン類の合成2017

    • Author(s)
      喜多悠二, 西本能弘, 千葉貢治, 安田 誠
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 新規有機アルミニウム錯体Pheox-AlおよびPhebox-Alの合成と触媒能評価2017

    • Author(s)
      西本能弘, 中尾秀一, 町中翔太, 安田 誠
    • Organizer
      第7回CSJ化学フェスタ
    • Related Report
      2017 Research-status Report
  • [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
      日本化学会代96春季年会
    • Place of Presentation
      慶応義塾大学
    • Related Report
      2016 Research-status 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
      日本化学会代96春季年会
    • Place of Presentation
      慶応義塾大学
    • Related Report
      2016 Research-status 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
      日本化学会代96春季年会
    • Place of Presentation
      慶応義塾大学
    • Related Report
      2016 Research-status 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
      日本化学会代96春季年会
    • Place of Presentation
      慶応義塾大学
    • Related Report
      2016 Research-status 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
      日本化学会代96春季年会
    • Place of Presentation
      慶応義塾大学
    • Related Report
      2016 Research-status 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
      日本化学会代96春季年会
    • Place of Presentation
      慶応義塾大学
    • Related Report
      2016 Research-status 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 Research-status 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、Kang Kyoungmin、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 Research-status Report
  • [Patent(Industrial Property Rights)] アルコキシヒドロシランの製造方法、及びアルコキシハロシランの製造方法2017

    • Inventor(s)
      佐藤章徳、安田誠、西本能弘
    • Industrial Property Rights Holder
      佐藤章徳、安田誠、西本能弘
    • Industrial Property Rights Type
      特許
    • Filing Date
      2017
    • Related Report
      2017 Research-status Report

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Published: 2016-04-21   Modified: 2020-03-30  

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