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2013 Fiscal Year Final Research Report

Development of chemical fixation of ubiquitous molecules with bifunctional molecular catalysts

Research Project

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Project/Area Number 22225004
Research Category

Grant-in-Aid for Scientific Research (S)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

IKARIYA Takao  東京工業大学, 理工学研究科, 教授 (30107552)

Co-Investigator(Renkei-kenkyūsha) KUWATA Shigeki  東京工業大学, 大学院・理工学研究科, 准教授 (10292781)
DGRIDNEV Ilya  東北大学, 大学院・理学研究科, 准教授 (60374906)
KAYAKI Yoshihito  東京工業大学, 大学院・理工学研究科, 助教 (20572704)
Project Period (FY) 2010-05-31 – 2014-03-31
Keywords協奏機能触媒 / 均一系触媒 / 不斉合成 / 水素化 / 小分子活性化
Research Abstract

On the basis of our accumulated knowledge in the bifunctional catalysis, we tried 1) to design new mono- and multi-nuclear transition metal-based complexes bearing cooperating ligands, and 2) to demonstrate perfect chemical reactions by extension of the scope of the applicability of the bifunctional catalysis, and finally 3) to explore the chemical fixation of the ubiquitous molecules into useful compounds and materials by development of the practical bifunctional molecular catalysts. The emergence of powerful bifunctional molecular catalysts provided efficient, sustainable and green production processes in the field of organic synthesis. In addition, the bifunctional catalyst promoted powerful chemical fixation technology of ubiquitous molecules including H2O, H2, O2, N2, and CO2 available in huge amounts can help to replace the fossil resources.

  • Research Products

    (38 results)

All 2013 2012 2011 2010 Other

All Journal Article (13 results) (of which Peer Reviewed: 13 results) Presentation (12 results) Book (5 results) Remarks (4 results) Patent(Industrial Property Rights) (4 results)

  • [Journal Article] Practical Selective Hydrogenation of α-Fluorinated Esters with Bifunctional Pincer-Type Ruthenium(II) Catalysts Leading to Fluorinated Alcohols or Fluoral Hemiacetals2013

    • Author(s)
      Takashi Ootsuka, Akihiro Ishii, Pavel A. Dub, Takao Ikariya
    • Journal Title

      J. Am. Chem. Soc

      Volume: Vol.135 Pages: 9600-9603

    • DOI

      10.1021/ja403852e

    • Peer Reviewed
  • [Journal Article] C-F Bond Breaking through Aromatic Nucleophilic Substitution with a Hydroxo Ligand Mediated via Water Bifunctional Activation2013

    • Author(s)
      Pavel A. Dub, Hui Wang, Asuka Matsunami, Ilya D. Gridnev, Shigeki Kuwata, Takao Ikariya
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: Vol. 86 Pages: 557-568

    • DOI

      10.1246/bcsj.20120359

    • Peer Reviewed
  • [Journal Article] N-N Bond Cleavage of Hydrazines with a Multiproton-Responsive Pincer-Type Iron Complex2013

    • Author(s)
      Kazuki Umehara, Shigeki Kuwata, Takao Ikariya
    • Journal Title

      J. Am. Chem. Soc

      Volume: Vol.135 Pages: 6754-6757

    • DOI

      10.1021/ja3122944

    • Peer Reviewed
  • [Journal Article] Quantum Chemical Calculations with the Inclusion of Nonspecific and Specific Solvation : Asymmetric Transfer Hydrogenation with Bifunctional Ruthenium Catalysts2013

    • Author(s)
      Pavel A. Dub, Takao Ikariya
    • Journal Title

      J. Am. Chem. Soc

      Volume: Vol.135 Pages: 2604-2619

    • DOI

      10.1021/ja3097674

    • Peer Reviewed
  • [Journal Article] Catalytic Reductive Transformations of Carboxylic and Carbonic Acid Derivatives Using Molecular Hydrogen2012

    • Author(s)
      Pavel A. Dub, Takao Ikariya
    • Journal Title

      ACS Catal

      Volume: Vol. 2 Pages: 1718-1741

    • DOI

      10.1021/cs300341g

    • Peer Reviewed
  • [Journal Article] Oxo-Tethered Ruthenium(II) Complex as a Bifunctional Catalyst for Asymmetric Transfer Hydrogenation and H_2 Hydrogenation2011

    • Author(s)
      Taichiro Touge, Tomohiko Hakamata, Hideki Nara, Tohru Kobayashi, Noboru Sayo, Takao Saito, Yoshihito Kayaki, Takao Ikariya
    • Journal Title

      J. Am. Chem. Soc

      Volume: Vol. 133 Pages: 14960-14963

    • DOI

      10.1021/ja207283t

    • Peer Reviewed
  • [Journal Article] H-H and N-H Bond Cleavage of Dihydrogen and Ammonia with Bifunctional Parent Imido (NH)-Bridged Diiridium Complex2011

    • Author(s)
      Takashi Kimura, Naoyuki Koiso, Koji Ishiwata, Shigeki Kuwata, Takao Ikariya
    • Journal Title

      J. Am. Chem. Soc

      Volume: Vol.133 Pages: 8880-8883

    • DOI

      10.1021/ja203538b

    • Peer Reviewed
  • [Journal Article] β-Protic Pyrazole and N-Heterocyclic Carbene Complexes : Synthesis, Properties, and Metal-Ligand Cooperative Bifunctional Catalysis2011

    • Author(s)
      Shigeki Kuwata, Takao Ikariya
    • Journal Title

      Chem. Eur. J

      Volume: Vol.17 Pages: 3542-3556

    • DOI

      10.1002/chem.201003296

    • Peer Reviewed
  • [Journal Article] Catalytic Hydrogenation of Carboxamides and Esters by Well-Defined Cp*Ru Complexes Bearing a Protic Amine Ligand2011

    • Author(s)
      Masato Ito, Takashi Ootsuka, Ryo Watari, Akira Shiibashi, Akio Himizu, Takao Ikariya
    • Journal Title

      J. Am. Chem. Soc

      Volume: Vol. 133 Pages: 4240-4242

    • DOI

      10.1021/ja1117254

    • Peer Reviewed
  • [Journal Article] Mechanism of Enantioselective C-C Bond Formation with Bifunctional Chiral Ru Catalysts : NMR and DFT Study2010

    • Author(s)
      Ilya D. Gridnev, Masahito Watanabe, Hui Wang, Takao Ikariya
    • Journal Title

      J. Am. Chem. Soc

      Volume: Vol. 132 Pages: 16637-16650

    • DOI

      10.1021/ja107597w

    • Peer Reviewed
  • [Journal Article] Enantioselective and Z/E-Selective Conjugate Addition of α-Substituted Cyanoacetates to Acetylenic Esters Catalyzed by Bifunctional Ruthenium and Iridium Complexes2010

    • Author(s)
      Yasuharu Hasegawa, Ilya D. Gridnev, Takao Ikariya
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: Vol. 49 Pages: 8157-8160

    • DOI

      10.1002/anie.201003585

    • Peer Reviewed
  • [Journal Article] Highly Enantioselective Hydrogenative Desymmetrization of Bicyclic Imides Leading to Multiply Functionalized Chiral Cyclic Compounds2010

    • Author(s)
      Masato Ito, Chika, Kobayashi, Akio Himizu, Takao Ikariya
    • Journal Title

      J. Am. Chem. Soc

      Volume: Vol. 132 Pages: 11414-11415

    • DOI

      10.1021/ja105048c

    • Peer Reviewed
  • [Journal Article] Quest for Metal/NH Bifunctional Bioinspired Catalysis in a Dinuclear Platform2010

    • Author(s)
      Shigeki Kuwata, Takao Ikariya
    • Journal Title

      Dalton Trans

      Pages: 2984-2992

    • DOI

      10.1039/B927357C

    • Peer Reviewed
  • [Presentation] Recent Progress in Concerto Molecular Catalysis with Bifunctional Catalysts2013

    • Author(s)
      Takao Ikariya
    • Organizer
      IUPAC 44th World Chemistry Congress
    • Place of Presentation
      Istanbul, Turkey
    • Year and Date
      20130811-16
  • [Presentation] 力量ある協奏機能分子触媒の開発2013

    • Author(s)
      碇屋隆雄
    • Organizer
      日本プロセス化学会2013サマーシンポジウム
    • Place of Presentation
      つくば国際会議場
    • Year and Date
      2013-07-18
  • [Presentation] Recent Progress in Concerto Molecular Catalysis2012

    • Author(s)
      Takao Ikariya
    • Organizer
      Chiral India 2012 (Chiral Technologies for Pharmaceutical Fine Chemicals)
    • Place of Presentation
      Hyderabad, India
    • Year and Date
      2012-12-05
  • [Presentation] ものづくりに役立つ革新的触媒の開発に向けて2012

    • Author(s)
      碇屋隆雄
    • Organizer
      第2回CSJフェスタ
    • Place of Presentation
      東京工業大学
    • Year and Date
      2012-10-26
  • [Presentation] Chemistry of Concerto Molecular Catalysis2011

    • Author(s)
      Takao Ikariya
    • Organizer
      Catalyst 2011, Dr. Reddy's Chemistry Conclave
    • Place of Presentation
      Hyderabad, India
    • Year and Date
      2011-12-16
  • [Presentation] Utilization of Carbon Dioxide in Organic Synthesis2011

    • Author(s)
      碇屋隆雄
    • Organizer
      第18回グリーンケミストリーフォーラム
    • Place of Presentation
      岡山コンベンションセンター
    • Year and Date
      2011-10-31
  • [Presentation] Activation of Molecular Hydrogen and Hydrogenation with Bifunctional Molecular Catalysis2011

    • Author(s)
      Takao Ikariya
    • Organizer
      Korea-Japan Joint Symposium on Organometallic and Coordination Chemistry
    • Place of Presentation
      Jeju, Korea
    • Year and Date
      2011-10-07
  • [Presentation] Recent Advances in Concerto Molecular Catalysis2011

    • Author(s)
      Takao Ikariya
    • Organizer
      France-Japan Joint Forum on Chemistry of Functional Organic Chemicals
    • Place of Presentation
      Université de Strasbourg, France
    • Year and Date
      2011-06-24
  • [Presentation] 協奏機能触媒の化学2011

    • Author(s)
      碇屋隆雄
    • Organizer
      有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      千葉大学
    • Year and Date
      2011-05-22
  • [Presentation] Carbon Dioxide as a Greener Solvent and Reactant for Catalytic Reactions2010

    • Author(s)
      Takao Ikariya
    • Organizer
      Green Solvent Conference
    • Place of Presentation
      ベルヒテスガーデン(ドイツ)
    • Year and Date
      20101010-13
  • [Presentation] Concerto Molecular Catalysis for Stereo-, Regio-, and Chemo-selective Transformation2010

    • Author(s)
      Takao Ikariya
    • Organizer
      Symposium Chiral China 2010
    • Place of Presentation
      天津(中国)
    • Year and Date
      2010-10-17
  • [Presentation] Oxidative Transformation with Bifunctional Molecular Catalysts2010

    • Author(s)
      Takao Ikariya
    • Organizer
      Presymposium of the 24th International Conference of Organometallic Chemistry
    • Place of Presentation
      台北(台湾)
    • Year and Date
      2010-07-18
  • [Book] 新しい溶媒を用いた有機合成2013

    • Author(s)
      榧木啓人, 碇屋隆雄
    • Total Pages
      1-28, 48-55
    • Publisher
      S&T 出版
  • [Book] Iridium, [N-[(1R,2R)-2-(amino-κN) cyclohexyl]-4-methylbenzenesulfonamidato-κN]chloro [(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4,-cyclopentadi en-1-yl]-, stereoisomer; Iridium, [N-[(1R,2R)-2-(amino-κN)cyclohexyl]-4-methylbenzenesulfonamidat o-κN]chloro[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4,-cyclopentadien-1-yl]-; Iridium, [N-[(1S,2S)-2- (amino-κN)cyclohexyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4,-cyclopent adien-1-yl]-, Stereoisomer, e-EROS Encyclopedia of Reagents for Organic Synthesis2013

    • Author(s)
      Takao Ikariya
    • Total Pages
      RN15097
    • Publisher
      John Wiley&Sons
  • [Book] Rhodium, [N-[(1S,2S)-2-(Amino-κN)-1,2-diphenyl-ethyl]-4-meth yl-benzenesulfonamidato-κN]chloro[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4,-cyclopentadien-1-yl]-, Stereoisomer, e-EROS Encyclopedia of Reagents for Organic Synthesis2012

    • Author(s)
      Takao Ikariya, Y oshihito Kayaki
    • Total Pages
      RN01400
    • Publisher
      John Wiley&Sons
  • [Book] グリーン反応媒体- 超臨界流体 : 二酸化炭素の固定化, 最新グリーンケミストリー 持続的社会のための化学, 御園生誠, 村橋俊一編2011

    • Author(s)
      碇屋隆雄, 榧木啓人
    • Total Pages
      219-227
    • Publisher
      講談社
  • [Book] Bifunctional Transition Metal -Based Molecular Catalysts for Asymmetric Syntheses, Topics in Organometallic Chemistry2011

    • Author(s)
      Takao Ikariya
    • Total Pages
      31-53
    • Publisher
      Springer
  • [Remarks] 本研究に関わる研究成果と,分子触媒化学の重要性を社会に向けて発信するために, 2005年ノーベル化学賞受賞者 Robert H. Grubbs 教授を招いた講演会「ノーベル化学賞と触媒」を平成25年7月29日に東京工業大学くらまえホールにて主催した. 一流の化学者が語る触媒研究の意義や楽しさを, 日本の将来を担う若者に直に感じて欲しいと考え, 大学学部生や高校生, 中学生にも広く参加を呼びかけた. その結果, 中学生~大学院学生を含め参加者は300余名に達した. 研究成果を広く伝えるだけでなく, 大学院生, 大学学部生, 高校生が英語で直接ノーベル化学賞受賞者と語り合う貴重な機会を提供することができた. なお「現代化学」 (東京化学同人)2013年10月号pp.60-61に, 当日の様子のレポートを掲載した. 関連ホームページ

    • URL

      http://www.apc.titech.ac.jp/~tikariya/Grubbs/

  • [Remarks] 碇屋隆雄,フンボルト賞(2011年)(主な受賞)

  • [Remarks] 碇屋隆雄,桑田繁樹ほか,日本化学会欧文誌 BCSJ 賞(2011年および 2013年)(主な受賞)

  • [Remarks] 碇屋隆雄,科学技術分野の文部科学大臣表彰科学技術賞(2014年)(主な受賞)

  • [Patent(Industrial Property Rights)] 1,3-ジアルキル-2-イミダゾリジノン類の製造方法2013

    • Inventor(s)
      關祐威, 小久保慶陽, 鈴木智之, 榧木啓人, 碇屋隆雄, 市川真一郎
    • Industrial Property Rights Holder
      国立大学法人東京工業大学・三井化学株式会社
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      5380051
    • Acquisition Date
      2013-10-04
  • [Patent(Industrial Property Rights)] 光学活性な含窒素化合物の製造方法2013

    • Inventor(s)
      渡辺正人, 村田邦彦, 碇屋隆雄
    • Industrial Property Rights Holder
      関東化学株式会社
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      5207096
    • Acquisition Date
      2013-03-01
  • [Patent(Industrial Property Rights)] 光学活性ニトロ化合物およびシアノ化合物の製造方法2011

    • Inventor(s)
      渡辺正人, 村田邦彦, 碇屋隆雄
    • Industrial Property Rights Holder
      関東化学株式会社
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      4744091
    • Acquisition Date
      2011-08-10
  • [Patent(Industrial Property Rights)] 光学活性アルコール化合物合成用触媒2010

    • Inventor(s)
      碇屋隆雄, 池平秀行, 村田邦彦, 清藤信夫, 大岡浩仁, 橋口昌平, 大熊毅, 野依良治
    • Industrial Property Rights Holder
      関東化学株式会社
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      4637876
    • Acquisition Date
      2010-12-03

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Published: 2015-06-25  

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