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2009 Fiscal Year Final Research Report

Development of environment-conscious synthetic reactions : construction of reaction coordinate-response catalyst

Research Project

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Project/Area Number 18002011
Research Category

Grant-in-Aid for Specially Promoted Research

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Chemistry
Research InstitutionKyushu University

Principal Investigator

KATSUKI Tsutomu  Kyushu University, 大学院・理学研究院, 教授 (40037271)

Co-Investigator(Kenkyū-buntansha) SAKAI Ken  九州大学, 大学院・理学研究院, 教授 (30235105)
UCHIDA Tatsuya  九州大学, 大学院・理学研究院, 助教 (50380564)
IRIE Ryo  九州大学, 大学院・理学研究院, 助教授 (70243889)
Co-Investigator(Renkei-kenkyūsha) MATSUMOTO Kazuhiro  九州大学, 大学院・理学研究院, 助教 (40512182)
Research Collaborator KAWABATA Hirotoshi  九州大学, 大学院・理学研究院, 博士研究員
EGAMI Hiromichi  九州大学, 大学院・理学研究院, 学術振興会特別研究員
SUEMATSU Hidehiro  九州大学, 大学院・理学研究院, 学術振興会特別研究員
Project Period (FY) 2006 – 2009
Keywords環境調和 / 多重機能触媒 / 過酸化水素水 / 分子状酸素 / 水素結合 / エポキシ化 / 光分子デバイス / 水素生成触媒
Research Abstract

Environment and resource conservation is the most urgent issue that human beings face. To address this issue and construct a sustainable society, development of selective, atom-efficient and eco-friendly synthetic reactions is essential. Biological material transformation systems are highly selective and atom-efficient and green, but several enzymes participate in most biological systems that are difficult to be implemented by the current chemical way. To realize equally green and efficient reactions with a catalyst, we designed complexes that can change their structure and exhibit an appropriate catalytic performance along reaction coordinate. With such complexes as catalyst, we could successfully achieve highly enantioselective and atom-efficient oxidation reactions using molecular oxygen or hydrogen peroxide as the terminal oxidant. This research demonstrated the effectiveness of a catalyst that can change its catalytic performance along reaction coordinate, for realizing a green reaction.

  • Research Products

    (36 results)

All 2010 2009 2008 2007 2006 Other

All Journal Article (29 results) Presentation (2 results) Book (3 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Frontier Orbital Engineering of Photo-Hydrogen-Evolving Molecular Devices: a Clear Relationship Between the H2-Evolving Activity and the Energy Level of the LUMO2010

    • Author(s)
      Shigeyuki Masaoka, Yuichiro Mukawa, Ken Sakai
    • Journal Title

      Dalton Trans. (in press)

  • [Journal Article] Photo-Hydrogen-Evolving Molecular Catalysts Consisting of Polypyridyl Ruthenium(II) Photosensitizers and Platinum(II) Catalysts: Insights into the Reaction Mechanism2010

    • Author(s)
      Hironobu Ozawa, Masayuki Kobayashi, Bijitha Balan, Shigeyuki Masaoka, Ken Sakai
    • Journal Title

      Chem. Asian J. (in press)

  • [Journal Article] Oxidation Catalysis of Nb(salan) Complexes: Asymmetric Epoxidation of Allylic Alcohols Using Aqueous Hydrogen Peroxide as Oxidant2010

    • Author(s)
      Hiromichi Egami, Takuya Oguma, Tsutomu Katsuki
    • Journal Title

      J. Am. Chem. Soc. 132

      Pages: 5886-5895

  • [Journal Article] Iridium(III)-Catalyzed Enantioselective Si-H Bond Insertion and Formation of Enantioenriched Silicon Center2010

    • Author(s)
      Yoichi Yasutomi, Hidehiro Suematsu, Tsutomu Katsuki
    • Journal Title

      J. Am. Chem. Soc. 132

      Pages: 4510-4511

  • [Journal Article] Photoinduced Electron Transfer in Tris(2, 2´-bipyridine)ruthenium(II)-Viologen Dyads with Peptide Backbones Leading to Long-Lived Charge Separation and Hydrogen Evolution2010

    • Author(s)
      Makoto Ogawa, Bijitha Balan, Gopalakrishnan Ajayakumar, Shigeyuki Masaoka, Heinz-Bernhard Kraatz, Masayasu Muramatsu, Syoji Ito, Yutaka Nagasawa, Hiroshi Miyasaka, Ken Sakai
    • Journal Title

      Dalton Trans. 39

      Pages: 4421-4434

  • [Journal Article] Ru(PPh3)(OH)-salen complex: a designer catalyst for chemoselective aerobic oxidation of primary alcohols2009

    • Author(s)
      Hirotaka Mizoguchi, Tatsuya Uchida, Kohichi Ishida, Tsutomu Katsuki
    • Journal Title

      Tetrahedron Lett. 50

      Pages: 3432-3435

  • [Journal Article] Iridium(III) Catalyzed Diastereo- and Enantioselective C-H Bond Functionalization2009

    • Author(s)
      Hidehiro Suematsu, Tsutomu Katsuki
    • Journal Title

      J. Am. Chem. Soc. 131

      Pages: 14218-14219

  • [Journal Article] Highly Enantioselective Epoxidation of Styrenes Catalyzed by Proline-Derived C1-Symmetric Titanium(Salan) Complexes2009

    • Author(s)
      Kazuhiro Matsumoto, Takuya Oguma, Tsutomu Katsuki
    • Journal Title

      Angew. Chem. Int. Ed. 48

      Pages: 7432-7435

  • [Journal Article] Highly Enantioselective Epoxidation of cis-Alkenylsilanes2009

    • Author(s)
      Kazuhiro Matsumoto, Takuya Kubo, Tsutomu Katsuki
    • Journal Title

      Chem. Eur. J. 15

      Pages: 6573-6575

  • [Journal Article] Evidence for Pt(II)-Based Molecular Catalysis in the Thermal Reduction of Water into Molecular Hydrogen2009

    • Author(s)
      Kosei Yamauchi, Shigeyuki Masaoka, Ken Sakai
    • Journal Title

      J. Am. Chem. Soc. 131

      Pages: 8404-8406

  • [Journal Article] Photo-Hydrogen-Evolving Activity of Chloro(terpyridine)platinum(II): a Single-Component Molecular Photocatalyst2009

    • Author(s)
      Reiko Okazaki, Shigeyuki Masaoka, Ken Sakai
    • Journal Title

      Dalton Trans.

      Pages: 6127-6133

  • [Journal Article] Iron-Catalyzed Asymmetric Aerobic Oxidation: Oxidative Coupling of 2-Naphthols2009

    • Author(s)
      Hiromichi Egami, Tsutomu Katsuki
    • Journal Title

      J. Am. Chem. Soc. 131

      Pages: 6082-6083

  • [Journal Article] Efficient Construction of α-Spirocyclopropyl Lactones: Iridium-Salen Catalyzed Asymmetric Cyclopropanation2009

    • Author(s)
      Masami Ichinose, Hidehiro Suematsu, Tsutomu Katsuki
    • Journal Title

      Angew. Chem. Int. Ed. 48

      Pages: 3121-3123

  • [Journal Article] Hydrogen Production from Water Catalyzed by an Air-stable Di-iron Complex with a Bio-relevant Fe2(m-S)2 Core2009

    • Author(s)
      Toshiki Yamaguchi, Shigeyuki Masaoka, Ken Sakai
    • Journal Title

      Chem. Lett. 38

      Pages: 434-435

  • [Journal Article] Clear Evidence Showing the Robustness of a Highly Active Oxygen-Evolving Mononuclear Ruthenium Complex with an Aqua Ligand2009

    • Author(s)
      Shigeyuki Masaoka, Ken Sakai
    • Journal Title

      Chem. Lett. 38

      Pages: 182-183

  • [Journal Article] μ-Oxo-μ-η^2:η^2-Peroxo Titanium Complex as a Reservoir of Active Species in Asymmetric Epoxidation Using Hydrogen Peroxide2008

    • Author(s)
      Shoichi Kondo, Kowichiro Saruhashi, Kenichi Seki, Koutatsu Matsubara, Katsuaki Miyaji, Takuya Kubo, Kazuhiro Matsumoto, Tsutomu Katsuki
    • Journal Title

      Angew. Chem. Int. Ed. 47

      Pages: 10195-10198

  • [Journal Article] Construction of Aryliridium-Salen Complexes: Enantio- and Cis-Selective Cyclopropanation of Conjugated and Non-conjugated Olefins2008

    • Author(s)
      Hidehiro Suematsu, Shigefumi Kanchiku, Tatsuya Uchida, Tsutomu Katsuki
    • Journal Title

      J. Am. Chem. Soc. 130

      Pages: 10327-10337

  • [Journal Article] Nb(salan)-Catalyzed Asymmetric Epoxidation of Allylic Alcohols with Hydorgen Peroxide2008

    • Author(s)
      Hiromichi Egami, Tsutomu Katsuki
    • Journal Title

      Angew. Chem. Int. Ed. 47

      Pages: 5171-5174

  • [Journal Article] Asymmetric Simmons-Smith Reaction of Allylic Alcohols with Al Lewis Acid/N Lewis Base Bifunctional Al(Salalen) Catalyst2008

    • Author(s)
      Hiroaki Shitama, Tsutomu Katsuki
    • Journal Title

      Angew. Chem. Int. Ed. 47

      Pages: 2450-2453

  • [Journal Article] Asymmetric oxidation of sulfides under solvent-free or highly concentrated conditions2008

    • Author(s)
      Kazuhiro Matsumoto, Tetsufumi Yamaguchi, Tsutomu Katsuki
    • Journal Title

      Chem. Commun.

      Pages: 1704-1706

  • [Journal Article] Asymmetric catalysis of metal complexes with non-planar ONNO ligands: Salen, Salalen and Salan2007

    • Author(s)
      Kazuhiro Matsumoto, Bunnai Saito, Tsutomu Katsuki
    • Journal Title

      Chem. Commun. (35)

      Pages: 619-3627

  • [Journal Article] Homogeneous catalysis of platinum(II) complexes in photochemical hydrogen production from water2007

    • Author(s)
      Ken Sakai, Hironobu Ozawa Coord
    • Journal Title

      Chem. Rev. 251

      Pages: 2753-2766

  • [Journal Article] An Effect of Structural Modification in the Photo-hydrogen-evolving RuIIPtII Dimers2007

    • Author(s)
      Hironobu Ozawa, Ken Sakai
    • Journal Title

      Chem. Lett. 36

      Pages: 920-921

  • [Journal Article] Syntheses, Characterization, and Photo-Hydrogen-Evolving Properties of Tris(2, 2'-bipyridine)ruthenium(II) Derivatives Tethered to a cis-Pt(II)Cl2 Unit: Insights into the Structure-Activity Relationship2007

    • Author(s)
      Hironobu Ozawa, Yuki Yokoyama, Masa-aki Haga, Ken Sakai
    • Journal Title

      Dalton Trans.

      Pages: 1197-1206

  • [Journal Article] Fe(salan)-Catalyzed Asymmetric Oxidation of Sulfides with Hydrogen Peroxide in Water2007

    • Author(s)
      Hiromichi Egami, Tsutomu Katsuki
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 8940-8941

  • [Journal Article] Asymmetric Oxidation Catalysis by a Chiral Al(salalen) Complex: Highly Enantioselective Oxidation of Sulfides with Aqueous Hydrogen Peroxide2007

    • Author(s)
      Tetsufumi Yamaguchi, Kazuhiro Matsumoto, Bunnai Saito, Tsutomu Katsuki
    • Journal Title

      Angew. Chem. Int. Ed. 46

      Pages: 4729-4731

  • [Journal Article] Titanium-Catalyzed Asymmetric Epoxidation of Non-Activated Olefins with Hydrogen Peroxide2007

    • Author(s)
      Yuji Sawada, Kazuhiro Matsumoto, Tsutomu Katsuki
    • Journal Title

      Angew. Chem. Int. Ed. 46

      Pages: 4559-4561

  • [Journal Article] Construction of an Aryliridium-salen Complex for Highly Cis- and Enantioselective Cyclopropanations2007

    • Author(s)
      Shigefumi Kanchiku, Hidehiro Suematsu, Kazuhiro Matsumoto, Tatsuya Uchida, Tsutomu Katsuki
    • Journal Title

      Angew. Chem. Int. Ed. 46

      Pages: 3889-3991

  • [Journal Article] Titanium(salan)-catalyzed Asymmetric Epoxidation with Aqueous Hydrogen Peroxide as Oxidant2006

    • Author(s)
      Yuji Sawada, Kazuhiro Matsumoto, Shoichi Kondo, Hisayuki Watanabe, Tomoyuki Ozawa, Kenji Suzuki, Bunnai Saito, Tsutomu Katsuki
    • Journal Title

      Angew. Chem. Int. Ed. 45

      Pages: 3478-3480

  • [Presentation] Tris(2, 2'-bipyridine)ruthenium(II)-Based Photo-Hydrogen-Evolving Molecular Devices Using Platinum(II)-Based Hydrogenic Activation2009

    • Author(s)
      Ken Sakai
    • Organizer
      18th International Symposium on Photochemistry and Photophysics of Coordination Compounds Gateaux Kingdom Sapporo Hotel & Spa Resort
    • Place of Presentation
      Sapporo, Japan
    • Year and Date
      20090604-20090609
  • [Presentation] Development of Atom-Efficient Asymmetric Oxygen Atom Transfer Reaction2008

    • Author(s)
      Tsutomu Katsuki
    • Organizer
      10th International Symposium: Activation of Dioxygen and Homogeneous Catalytic Oxidation
    • Place of Presentation
      San Servolo, Venice, Italy(plenary lecture)
    • Year and Date
      20080720-20080725
  • [Book] Asymmetric Oxidations and Related Reactions(ed by Ojima, I., Catalytic Asymmetric Synthesis (third edition))2010

    • Author(s)
      Kazuhiro Matsumoto, Tsutomu Katsuki.
    • Total Pages
      839-890
    • Publisher
      Wiley-VCH
  • [Book] 白金(II)錯体を水素生成触媒とする単一分子水素発生デバイスの開発(配位空間の化学-最新技術と応用-(北川進監修))2009

    • Author(s)
      酒井健
    • Total Pages
      214-222
    • Publisher
      シーエムシー出版
  • [Book] Asymmetric Epoxidation of Non-Activated Olefins(ed by S. Brase and M. Christmann, Asymmetric Synthesis -The Essentials)2007

    • Author(s)
      Kazuhiro Matsumoto, Tsutomu Katsuki.
    • Total Pages
      116-120
    • Publisher
      Wiley-VCH
  • [Remarks]

    • URL

      http://www.scc.kyushu-u.ac.jp/Yuhan/main/publish/SPR.htlm

  • [Patent(Industrial Property Rights)] 光学活性エポキシ化合物の製造方法、並びに用いる配位子、錯体、該配位子の製造方法、及び該錯体の製造方法2009

    • Inventor(s)
      松本和弘、小熊卓也、近藤章一、栗原一典、香月勗
    • Industrial Property Rights Holder
      日産化学工業株式会社および国立大学人九州大学
    • Industrial Property Number
      特許願・特願2009-168885
    • Filing Date
      2009-07-17

URL: 

Published: 2011-06-18   Modified: 2016-04-21  

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