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Study of Oxidative Coupling by Ru(0) and Mechanistic Insight of the Selectivities

Research Project

Project/Area Number 23550117
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionTokyo University of Agriculture and Technology

Principal Investigator

HIRANO Masafumi  東京農工大学, 工学(系)研究科(研究院), 准教授 (70251585)

Project Period (FY) 2011 – 2013
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2011: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsルテニウム(0) / 酸化的カップリング / 置換アルケン / 共役ジエン / 鎖状交差二量化 / ルテニウム / 共役化合物 / 共役カルボニル化合物 / アレン / ケテン / ジアステレオ選択性 / 化学選択性 / 位置選択性
Research Abstract

A zero-valent ruthenium complex having a naphthalene ligand readily releases the naphthalene to generate a 6-electron vacant site. A conjugated compound and a substituted alkene are able to coordinate to the vacant site as 4- and 2-pi donors, respectively. This catalyst therefore clearly recognizes these two substrates by the donor electrons and the cross-dimerization can be achieved. This mechanistic study reveals the oxidative coupling mechanism for present coupling reaction. To use the advantages of this mechanism, we have succeeded to develop the stereoselective reactions.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • 2011 Research-status Report
  • Research Products

    (99 results)

All 2014 2013 2012 2011 Other

All Journal Article (21 results) (of which Peer Reviewed: 21 results) Presentation (76 results) (of which Invited: 11 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Cross-dimerization between Different cisoid- and transoid-1, 3-Dienes at a Ruthenium(0) Center2013

    • Author(s)
      Masafumi Hirano, Haruka Inoue, Takuya Okamoto, Takao Ueda, Nobuyuki Komine, Sanshiro Komiya, Xian-qi Wang, and Martin A. Bennett
    • Journal Title

      New J. Chem

      Volume: 37 Pages: 3433-3439

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Cross-dimerization between Methyl Methacrylate and Substituted Alkenes by Ru(0)-Bicyclononadiene Complex2013

    • Author(s)
      Yuki Hiroi, Nobuyuki Komine, Sanshiro Komiya, and Masafumi Hirano
    • Journal Title

      Org. Lett

      Volume: 15 Pages: 2486-2489

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] ross-dimerization between Different cisoid- and transoid-1,3-Dienes at a Ruthenium(0) Center2013

    • Author(s)
      Masafumi Hirano,* Haruka Inoue, Takuya Okamoto, Takao Ueda, Nobuyuki Komine, Sanshiro Komiya, Xian-qi Wang, and Martin A. Bennett,*
    • Journal Title

      New J. Chem.

      Volume: 37 Issue: 11 Pages: 3433-3439

    • DOI

      10.1039/c3nj00429e

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Cross-dimerization between Methyl Methacrylate and Substituted Alkenes by Ru(0)-Bicyclononadiene Complex2013

    • Author(s)
      Yuki Hiroi, Nobuyuki Komine, Sanshiro Komiya, and Masafumi Hirano,*
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 10 Pages: 2486-2489

    • DOI

      10.1021/ol400963d

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Thiirane Desulfurization Controlled by a Bridging or Terminal Acyl Ligand: Concerted vs SN2 Pathways2013

    • Author(s)
      Matthew T. Zamora, Kenta Oda, Nobuyuki Komine, Masafumi Hirano, and Sanshiro Komiya
    • Journal Title

      J. Organomet. Chem.

      Volume: in press

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stoichiometric and Carbon-Hydrogen Bond Cleavage Reaction in a Bis(carboxylato)ruthenium(II) Complex and Its Application to Catalytic H/D Exchange Reaction of Carboxylic Acids2013

    • Author(s)
      Masafumi Hirano, Ryo Fujimoto, Kohei Hatagami, Nobuyuki Komine, and Sanshiro Komiya
    • Journal Title

      ChemCatChem

      Volume: 5 Issue: 5 Pages: 1101-1115

    • DOI

      10.1002/cctc.201200686

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stoichiometric Carbon-Carbon Bond Forming Reaction of 1, 3-Diene with 1, 2-Diene in a Ruthenium(0) Complex2012

    • Author(s)
      Masafumi Hirano, Takuya Okamoto, Nobuyuki Komine, and Sanshiro Komiya
    • Journal Title

      Organometallics

      Volume: 31 Pages: 4639-4642

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stoichiometric and Catalytic Cross Dimerization between Conjugated Dienes and Conjugated Carbonyls by a Ruthenium(0) Complex. Straightforward Access to Unsaturated Carbonyl Compounds by an Oxidative Coupling Mechanism2012

    • Author(s)
      Masafumi Hirano, Yasutomo Arai, Yuka Hamamura, Nobuyuki Komine, and Sanshiro Komiya
    • Journal Title

      Organometallics

      Volume: 31 Pages: 4006-4019

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Conjugated Diene Complexes of Ruthenium(0) Derived from Ru(η^6-naphthalene)(η^4-1, 5-COD) : Z to E Isomerisation of Coordinated 1, 3-Pentadiene2012

    • Author(s)
      Masafumi Hirano, Yumiko Sakate, Haruka Inoue, Yasutomo Arai, Nobuyuki Komine, Sanshiro Komiya, Xian-qi Wang, Martin A. Bennett
    • Journal Title

      J. Organomet. Chem

      Volume: 708-709 Pages: 45-57

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stoichiometric Carbon-Carbon Bond Forming Reaction of 1,3-Diene with 1,2-Diene in a Ruthenium(0) Complex2012

    • Author(s)
      Masafumi Hirano, Takuya Okamoto, Nobuyuki Komine, and Sanshiro Komiya
    • Journal Title

      Organometallics

      Volume: 31 Issue: 13 Pages: 4639-4642

    • DOI

      10.1021/om300326q

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stoichiometric and Catalytic Cross Dimerization between Conjugated Dienes and Conjugated Carbonyls by a Ruthenium(0) Complex. Straightforward Access to Unsaturated Carbonyl Compounds by an Oxidative Coupling Mechanism2012

    • Author(s)
      Masafumi Hirano, Yasutomo Arai, Yuka Hamamura, Nobuyuki Komine, and Sanshiro Komiya
    • Journal Title

      Organometallics

      Volume: 31 Issue: 10 Pages: 4006-4019

    • DOI

      10.1021/om300234d

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] 0価ルテニウム錯体による置換アルケンおよびジエン類の触媒的鎖状カップリング反応:酸化的カップリング機構による化学,位置およびジアステレオ選択的炭素ー炭素結合形成反応2012

    • Author(s)
      平野雅文、小峰伸之,小宮三四郎
    • Journal Title

      有機合成化学協会誌

      Volume: 70 Pages: 1267-1280

    • NAID

      10031137477

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Acid-Promoted sp^3 C-H Bond Cleavage in a Series of (2-Allylphenoxo) ruthenium(II) Complexes. Mechanistic Insight into the Aryloxo-Acid Interaction and Bond Cleavage Reaction2012

    • Author(s)
      M.Hirano, M.Murakami, T.Kuga, N.Komine, S.Komiya
    • Journal Title

      Organometallics

      Volume: 31 Issue: 1 Pages: 381-393

    • DOI

      10.1021/om200974c

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Conjugated Diene Complexes of Ruthenium(0) Derived from Ru(η^6-naphthalene)(η^4-1,5-COD) : Z to E Isomerisation of Coordinated 1,3-Pentadiene2012

    • Author(s)
      M.Hirano, Y.Sakate, H.Inoue, Y.Arai, N.Komine, S.Komiya, X.Wang, M.A.Bennett
    • Journal Title

      Journal of Organometallic Chemistry

      Volume: (in press) Pages: 46-57

    • DOI

      10.1016/j.jorganchem.2012.02.018

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Prostereogenic Face and Orientational Control of Coordinated Olefins at Ru(0) in Oxidative Coupling Reaction between Methyl Methacrylate and 2, 5-Dihydrofuran2011

    • Author(s)
      Yuki Hiroi, Nobuyuki Komine, Masafumi Hirano, and Sanshiro Komiya
    • Journal Title

      Organometallics

      Volume: 30 Pages: 1307-1310

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stoichiometric Regio- and Stereoselective Oxidative Coupling Reaction of Conjugated Dienes with Ruthenium(0). A Mechanistic Insight into the Origin of Selectivity2011

    • Author(s)
      Masafumi Hirano, Yumiko Sakate, Nobuyuki Komine, Sanshiro Komiya, Xian-qi Wang, Martin A. Bennett
    • Journal Title

      Organometallics

      Volume: 30 Pages: 768-777

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stoichiometric Regio- and Stereoselective Oxidative Coupling Reaction of Conjugated Dienes with Ruthenium(0). A Mechanistic Insight into the Origin of Selectivity2011

    • Author(s)
      M.Hirano, Y.Sakate, N.Komine, S.Komiya, X.Wang, M.A.Bennett
    • Journal Title

      Organometallics

      Volume: 30 Issue: 4 Pages: 768-777

    • DOI

      10.1021/om100956f

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Prostereogenic Face and Orientational Control of Coordinated Olefinsat Ru(0) in Oxidative Coupling Reaction between Methyl Methacrylate and 2,5-Dihydrofuran2011

    • Author(s)
      Y.Hiroi, N.Komine, M.Hirano, S.Komiya
    • Journal Title

      Organometallics

      Volume: 30 Issue: 6 Pages: 1307-1310

    • DOI

      10.1021/om200091n

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Carbon-Hydrogen Bond Cleavage Reaction in Four-Coordinate (2,6-Dimethylbenzenethiolato) platinum(II) Complexes. Dramatic Acceleration by Thiolato Hydrogen Accentor2011

    • Author(s)
      M.Hirano, S.Tatesawa, M.Yabukami, Y.Ishihara, Y.Hara, N.Komine, S.Komiya
    • Journal Title

      Organometallics

      Volume: 30 Issue: 19 Pages: 5110-5122

    • DOI

      10.1021/om200345h

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Heterodinuclear Ruthenium-manganese Complex Having μ-Benzylidene Ligand2011

    • Author(s)
      S.Tanaka, N.Komine, M.Hirano, S.Komiya
    • Journal Title

      J.Organomet.Chem.

      Volume: 696 Issue: 2 Pages: 632-635

    • DOI

      10.1016/j.jorganchem.2010.09.020

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Branch Selective Allylation of Acetylacetone Catalyzed by Water-soluble Rhodium Complex Catalyst2011

    • Author(s)
      N.Komine, K.Ishiguro, S.Kanai, M.Hirano, S.Komiya
    • Journal Title

      J.Organomet.Chem.

      Volume: 696 Issue: 10 Pages: 1927-1930

    • DOI

      10.1016/j.jorganchem.2010.10.037

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] Chemo-, Regio-, Diastereo- and Enantioselective Coupling of Substituted Alkenes by Ru(0)2014

    • Author(s)
      Masafumi Hirano
    • Organizer
      Minisymposium on Design of Efficient Molecular Catalysis for Environmental Benign Chemical Process and Materials
    • Place of Presentation
      Tokyo
    • Year and Date
      2014-06-30
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] 環状ジエンを支持配位子とする新規ルテニウム0価錯体の合成と置換アルケンの触媒的交差二量化反応への応用2014

    • Author(s)
      廣井結希, 小峰伸之, 小宮三四郎, 平野雅文
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      (名古屋)名古屋大学
    • Year and Date
      2014-03-27
    • Related Report
      2013 Final Research Report
  • [Presentation] Catalytic Cross-Dimerization between Conjugated Dienes and Styrenes by Ruthenium(0) Complex2014

    • Author(s)
      UEDA, Takao ; KOMINE, Nobuyuki ; KOMIYA, Sanshiro ; HIRANO, Masafumi
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      (名古屋)名古屋大学
    • Year and Date
      2014-03-27
    • Related Report
      2013 Final Research Report
  • [Presentation] 環状ジエンを支持配位子とする新規ルテニウム0価錯体の合成と置換アルケンの触媒的交差二量化反応への応用2014

    • Author(s)
      廣井 結希、小峰 伸之、小宮 三四郎、平野 雅文
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] Catalytic Cross-Dimerization between Conjugated Dienes and Styrenes by Ruthenium(0) Complex2014

    • Author(s)
      UEDA, Takao; KOMINE, Nobuyuki; KOMIYA, Sanshiro; HIRANO, Masafumi
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] Regio-, Diastereo- and Enantioselective Coupling Using Methyl Methacrylate by Ru(0) Complex2013

    • Author(s)
      Masafumi Hirano
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2013
    • Place of Presentation
      Beijin (China)
    • Year and Date
      2013-12-05
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] Controlled Dimerization Using Acrylates Catalyzed by Ru(0) Complexes2013

    • Author(s)
      Masafumi Hirano
    • Organizer
      Surface and Catalysis for Greener Future : C&FC Pre-Symposium in Himeji
    • Place of Presentation
      Himeji
    • Year and Date
      2013-11-29
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] Synthesis of Chiral Bicyclo[3.3.1]nonadiene Complexes of Ru(0) and Their Use in Catalytic Cross-Dimerization of Alkenes2013

    • Author(s)
      Masafumi Hirano
    • Organizer
      The International Symposium on Organic Reaction
    • Place of Presentation
      ISOR, Taipei, (Taiwan)
    • Year and Date
      2013-11-22
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] Ru(0)錯体上での共役ジエンと置換アルケンとの反応における位置選択性2013

    • Author(s)
      上田貴生・新井康友・小峰伸之・小宮三四郎・平野雅文
    • Organizer
      錯体化学討論会第63回討論会
    • Place of Presentation
      (那覇)琉球大学
    • Year and Date
      2013-11-03
    • Related Report
      2013 Final Research Report
  • [Presentation] ルテニウム(0)錯体上での配位共役1, 3-ジエンとクムレン型化合物の酸化的カップリング反応2013

    • Author(s)
      岡本拓也・小峰伸之・平野雅文・小宮三四郎
    • Organizer
      錯体化学会第63回討論会
    • Place of Presentation
      (那覇)琉球大学
    • Year and Date
      2013-11-03
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis of New Ru(0) Complexes Having a Cyclic Diene Ligand and Their Application to Catalytic Enantioselective Linear Cross-Dimerization of Substituted Alkene2013

    • Author(s)
      廣井結希, 小峰伸之, 小宮三四郎, 平野雅文
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      (目白)学習院大学
    • Year and Date
      2013-09-12
    • Related Report
      2013 Final Research Report
  • [Presentation] Enantioselective Cross-Dimerization between Methyl Methacrylate and Substituted Alkene through Oxidative Coupling Step2013

    • Author(s)
      Masafumi Hirano, Yuki Hiroi, Nobuyuki Komine, and Sanshiro Komiya
    • Organizer
      OMCOS
    • Place of Presentation
      Fort Collins (USA)
    • Year and Date
      2013-07-30
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis of New Ru(0) Complexes Having a Chiral Diene Ligand and their Application to Catalytic Enantioselective Linear Cross-dimerization of Substituted Alkene2013

    • Author(s)
      Yuki Hiroi, Nobuyuki Komine, Sanshiro Komiya, and Masafumi Hirano
    • Organizer
      The 3rd International Symposium on Molecular Activation (ISMA3)
    • Place of Presentation
      USA
    • Year and Date
      2013-07-30
    • Related Report
      2013 Final Research Report
  • [Presentation] Regio-, Diastereo- and Enantioselective Coupling Using Methyl Methacrylate by Ru(0) Complex2013

    • Author(s)
      Masafumi Hirano
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2013
    • Place of Presentation
      Renming University (China)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Controlled Dimerization Using Acrylates Catalyzed by Ru(0) Complexes2013

    • Author(s)
      Masafumi Hirano
    • Organizer
      Surface and Catalysis for Greener Future: C&FC Pre-Symposium in Himeji
    • Place of Presentation
      イーグレひめじ
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Synthesis of Chiral Bicyclo[3.3.1]nonadiene Complexes of Ru(0) and Their Use in Catalytic Cross-Dimerization of Alkenes2013

    • Author(s)
      Masafumi Hirano
    • Organizer
      The International Symposium on Organic Reaction, ISOR
    • Place of Presentation
      Howard International House (Taiwan)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Ru(0)錯体上での共役ジエンと置換アルケンとの反応における位置選択性2013

    • Author(s)
      上田 貴生、新井 康友、小峰 伸之、小宮 三四郎、平野 雅文
    • Organizer
      錯体化学討論会第63回討論会
    • Place of Presentation
      琉球大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] ルテニウム(0)錯体上での配位共役1,3-ジエンとクムレン型化合物の酸化的カップリング反応2013

    • Author(s)
      岡本 拓也、小峰 伸之、平野 雅文、小宮 三四郎
    • Organizer
      錯体化学討論会第63回討論会
    • Place of Presentation
      琉球大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] Synthesis of New Ru(0) Complexes Having a Cyclic Diene Ligand and Their Application to Catalytic Enantioselective Linear Cross-Dimerization of Substituted Alkene2013

    • Author(s)
      廣井結希、小峰伸之、小宮三四郎、平野雅文
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] ルテニウム (0) 錯体 上での配位共役ジエンと 共役ジエンおよび置換ア ルケンとの反応機構2013

    • Author(s)
      平野 雅文、井上 晴香 、上田 貴生、小峰 伸之、小宮三四郎
    • Organizer
      第112回触媒討論会
    • Place of Presentation
      秋田大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] Enantioselective Cross-Dimerization between Methyl Methacrylate and Substituted Alkene through Oxidative Coupling Step2013

    • Author(s)
      Masafumi Hirano, Yuki Hiroi, Nobuyuki Komine, and Sanshiro Komiya
    • Organizer
      OMCOS17
    • Place of Presentation
      Lincoln Center, Fort Collins (USA)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Synthesis of New Ru(0) Complexes Having a Chiral Diene Ligand and their Application to Catalytic Enantioselective Linear Cross-dimerization of Substituted Alkene2013

    • Author(s)
      Yuki Hiroi, Nobuyuki Komine, Sanshiro Komiya, and Masafumi Hirano
    • Organizer
      The 3rd International Symposium on Molecular Activation(ISMA3)
    • Place of Presentation
      Shelaton Steamboat (USA)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Chemo-, Regio-, Diastereo- and Enantioselective Coupling of Substituted Alkenes by Ru(0) Complex2013

    • Author(s)
      Masafumi Hirano
    • Organizer
      The 3rd International Symposium on Molecular Activation
    • Place of Presentation
      Shelaton Steamboat (USA)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Asymmetric Linear Cross-Dimerization of Methyl Methacrylate by Ru(0) Complexes2013

    • Author(s)
      Masafumi Hirano, Yuki Hiroi, Nobuyuki Komine, and Sanshiro Komiya
    • Organizer
      96th Canadian Chemistry Conference
    • Place of Presentation
      Qubec Convention Centre (Canada)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 0価ルテニウム錯体触媒による置換アルケン類の化学、位置および立体選択的鎖状二量化反応2013

    • Author(s)
      平野雅文
    • Organizer
      触媒学会埼玉地区講演会
    • Place of Presentation
      浦和、埼玉大学
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] 高いヒドロメタル化触媒活性を有するモノ(ホスフィン)パラジウム(0)錯体とフマル酸ジメチルの反応2013

    • Author(s)
      伊藤 涼、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津、立命館大学びわこくさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] 酸化還元活性な2,6-ビス(ピロリル)ピリジン型配位子を有するパラジウムおよび白金錯体の合成と反応2013

    • Author(s)
      小峰伸之、須田裕美、平野雅文、小宮三四郎
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津、立命館大学びわこくさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] (共役ジエン)ルテニウム0価錯体と置換アルケンとの酸化的カップリング反応における位置選択性支配因子2013

    • Author(s)
      上田貴生、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津、立命館大学びわこくさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] ルテニウム(0)錯体上での配位共役1,3-ジエンとケテンの酸化的カップリング反応2013

    • Author(s)
      岡本拓也、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津、立命館大学びわこくさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] キラルジエンを支持配位子とする新規ルテニウム0価錯体の合成とメタクリル酸エステルと置換オレフィンの不斉鎖状交差二量化反応への応用2013

    • Author(s)
      廣井結希、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津、立命館大学びわこくさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] オルトエチル基の連続的C-H結合切断反応による不飽和オキサルテナサイクルの形成と反応2013

    • Author(s)
      Endin Mulyadi、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津、立命館大学びわこくさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] 可視光により促進されるジメチルアリール(ビピリジン)白金ーマンガンへテロ二核錯体のメチル基移動反応2013

    • Author(s)
      小田切達也、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津、立命館大学びわこくさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] Formation of a Thiocarboxylato-Bridged Pt-Mn Complex by Desulfurization of Thiiranes: Mechanism and Reactivity2013

    • Author(s)
      Zamora Matthew Thoamas, 小峰伸之、平野雅文、小宮三四郎
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津、立命館大学びわこくさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] Cross Dimerization between Substituted 1,3-Dienes and Electron Deficient Olefins by Ru(0) Complex2012

    • Author(s)
      Masafumi Hirano, Yasutomo Arai, Nobuyuki Komine and Sanshiro Komiya
    • Organizer
      The 18th International Symposium on Homogeneous Catalysis
    • Place of Presentation
      Toulouse, France, Pierre Baudis Conference Centre
    • Related Report
      2012 Research-status Report
  • [Presentation] Catalytic Addition of Tungsten Hydride to Alkenes and Alkynes Promoted by Mono(phosphine or phosphite)palladium(0) Complex2012

    • Author(s)
      Ryo Ito, Nobuyuki Komine, Masafumi Hirano and Sanshiro Komiya
    • Organizer
      The 25th International Conference on Organometallic Chemistry
    • Place of Presentation
      Lisbon, Portugal, Lisbon University
    • Related Report
      2012 Research-status Report
  • [Presentation] Intermolecular sp3 C-H Bond Cleavage Reaction of Bis(2,6-dimethylbenzenethiolato) Goup 10 Metal Complexes2012

    • Author(s)
      Yusuke Hara, Nobuyuki Komine, Masafumi Hirano, and Sanshiro Komiya
    • Organizer
      The 25th International Conference on Organometallic Chemistry
    • Place of Presentation
      Lisbon, Portugal, Lisbon University
    • Related Report
      2012 Research-status Report
  • [Presentation] Synthesis of Ru(0) Complexes Having a Bicyclononadiene Ligand and Their Application to Catalytic Selective Dimerization of Substituted Alkenes2012

    • Author(s)
      Yuki Hiroi, Nobuyuki Komine, Masafumi Hirano and Sanshiro Komiya
    • Organizer
      The 25th International Conference on Organometallic Chemistry
    • Place of Presentation
      Lisbon, Portugal, Lisbon University
    • Related Report
      2012 Research-status Report
  • [Presentation] Regio- and Prostereogenic Face Selective Oxidative Coupling Reaction of Coordinated 1,3-Diene with 1,2-Diene at Ruthenium(0) Complex2012

    • Author(s)
      Takuya Okamoto, Nobuyuki Komine, Masafumi Hirano and Sanshiro Komiya
    • Organizer
      The 25th International Conference on Organometallic Chemistry
    • Place of Presentation
      Lisbon, Portugal, Lisbon University
    • Related Report
      2012 Research-status Report
  • [Presentation] E-Selective Reactions in Heterodinuclear h1:h2-Crotylplatinum-transion Metal Complexes2012

    • Author(s)
      Sanshiro Komiya, Toshiki Nakano, Nobuyuki Komine and Masafumi Hirano
    • Organizer
      The 40th International Conference of Coordination Chemistry
    • Place of Presentation
      Valencia, Spain, The Conference Centre in Valencia
    • Related Report
      2012 Research-status Report
  • [Presentation] Selective Homo- and Cross Dimerizations os Substituted Alkenes Catalyzed by Ruthenium(0) Complex Having a Cyclic Diene Ligand2012

    • Author(s)
      Yuki Hiroi, Nobuyuki Komine, Masafumi Hirano and Sanshiro Komiya
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪、大阪大学吹田キャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] Synthesis and Reactivity Differences of Bridged and Non-Bridged Dinuclear Pt/Mn Complexes with Thiiranes2012

    • Author(s)
      Zamora Matthew Thomas, Kenta Oda, Nobuyuki Komine, Masafumi Hirano, and Sanshiro Komiya
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪、大阪大学吹田キャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] Visible Light Induced M-C Bond Forming Reductive Elimination of Heterodinuclear Organoplatinum-manganese Complex2012

    • Author(s)
      Sanshiro Komiya, Tatsuya Odagiri, Nobuyuki Komine, and Masafumi Hirano
    • Organizer
      International Conference of Catalysis in Organic Synthesis
    • Place of Presentation
      Moscow, Russia, Zelinsky Institute
    • Related Report
      2012 Research-status Report
  • [Presentation] Reaction of 1,3-Diene Complex of Ru(0) with Conjugated Cabonyls, 1,3-Dienes, and 1,2-Dienes: Straightforward Access to Unsaturated Carbonyl Compounds by a Ru(0) Compound2012

    • Author(s)
      Masafumi Hirano, Yuki Hiroi, Nobuyuki Komine, and Sanshiro Komiya
    • Organizer
      International Conference of Catalysis in Organic Synthesis
    • Place of Presentation
      Moscow, Russia, Zelinsky Institute
    • Related Report
      2012 Research-status Report
  • [Presentation] 2,6-ジメチルベンゼンカルコゲナト基を持つ10族金属錯体の分子内sp3炭素ー水素結合切断反応2012

    • Author(s)
      原 優介、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      錯体化学会第62回討論会
    • Place of Presentation
      富山、富山大学五福キャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] モノまたはビス(リン配位子)パラジウム(0)錯体触媒によるヒドリドタングステンのアルケンやアルキンへの付加反応2012

    • Author(s)
      伊藤 涼、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      錯体化学会第62回討論会
    • Place of Presentation
      富山、富山大学五福キャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] μ-η1:η2-アリル白金-マンガン(またはレニウム)二核錯体の合成とE 体選択的還元的脱離反応2012

    • Author(s)
      仲野俊樹、小峰伸之,平野雅文、小宮三四郎
    • Organizer
      第110回触媒討論会
    • Place of Presentation
      福岡、九州大学伊都キャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] ルテニウム(0)錯体上での1,3-ジエンと1,2-ジエンの位置および面選択性酸化的カップリング反応2012

    • Author(s)
      岡本拓也、小峰伸之,平野雅文、小宮三四郎
    • Organizer
      第110回触媒討論会
    • Place of Presentation
      福岡、九州大学伊都キャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] A Mechanistic Insight into sp3 Carbon-Hydrogen Bond Activation in (2-Allylaryloxo)ruthenium(II) Promoted by Acid2012

    • Author(s)
      Masafumi Hirano
    • Organizer
      17th Malaysian Chemical Congress
    • Place of Presentation
      Kuala Lumpur, Malaysia, Putra World Trade Centre
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] Synthesis and Reactivity Differences of Bridged and Non-Bridged Dinuclear Pt/Mn Complexes with Thiiranes2012

    • Author(s)
      Zamora Matthew Thomas, Kenta Oda, Nobuyuki Komine, Masafumi Hirano, and Sanshiro Komiya
    • Organizer
      The 11th International Symposium on Advanced Technology (ISAT-Special)
    • Place of Presentation
      八王子、工学院大学八王子キャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] Mechanistic Insights into Acid-Promoted sp3 C-H Bond Activation in (Aryloxo)ruthenium(II)2012

    • Author(s)
      Masafumi Hirano, Masahiro Murakami, Toshinori Kuga, Nobuyuki Komine, and Sanshiro Komiya
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      京都、リーガロイヤルホテル京都
    • Related Report
      2012 Research-status Report
  • [Presentation] New sp3 C-H Bond Activation Mechanism Promoted by Acid: Mechanistic Insight into the Interaction between (2-Allylphenoxo)ruthenium(II) and Acid Molecules2012

    • Author(s)
      M. Hirano, M. Murakami, N. Komine, and S. Komiya
    • Organizer
      International Green Catalysis Symposium
    • Place of Presentation
      レンヌ(フランス)
    • Related Report
      2011 Research-status Report
  • [Presentation] Chemo-, Regio- and Diastereoselective Cross Dimerization between Methyl Methacrylate and 2,5-Dihydrofuran Catalyzed by Ru(0) Complex2012

    • Author(s)
      M. Hirano, Y. Hiroi, N. Komine, and S. Komiya
    • Organizer
      International Green Catalysis Symposium
    • Place of Presentation
      レンヌ(フランス)
    • Related Report
      2011 Research-status Report
  • [Presentation] ルテニウム(0)錯体上での配位共役ジエンとアレンの酸化的カップリング反応2012

    • Author(s)
      岡本拓也、平野雅文、小宮三四郎
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      日吉(神奈川)
    • Related Report
      2011 Research-status Report
  • [Presentation] ルテニウム(0)錯体を用いた分岐型共役ジエンと分岐型共役カルボニル化合物の化学選択的共二量化反応2012

    • Author(s)
      新井康友、濱村友香、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      日吉(神奈川)
    • Related Report
      2011 Research-status Report
  • [Presentation] ビシクロノナジエンを配位子として持つRu(0)錯体の合成と置換オレフィンの選択的共二量化反応への応用2012

    • Author(s)
      広井結希、平野雅文、小宮三四郎
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      日吉(神奈川)
    • Related Report
      2011 Research-status Report
  • [Presentation] (2,6-ジエチルフェノキソ)ルテニウム(II)錯体のオルトエチル基の連続的C-H結合の切断反応2012

    • Author(s)
      柳澤泰斗、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      日吉(神奈川)
    • Related Report
      2011 Research-status Report
  • [Presentation] ビス(2,6-ジメチルベンゼンチオラト)ニッケル(II)錯体の合成と分子内sp3炭素―水素...2012

    • Author(s)
      金曽祐一、平野雅文、小宮三四郎
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      日吉(神奈川)
    • Related Report
      2011 Research-status Report
  • [Presentation] モノ(ホスフィンまたはホスファイト)パラジウム(0)錯体触媒によるタングステン...2012

    • Author(s)
      伊藤 涼、池田孝裕、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      日吉(神奈川)
    • Related Report
      2011 Research-status Report
  • [Presentation] μ-η1:η2-クロチル白金-マンガン二核錯体の合成とE選択的金属間アリル基移動反応2012

    • Author(s)
      仲野俊樹、齋藤 駿、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      日吉(神奈川)
    • Related Report
      2011 Research-status Report
  • [Presentation] 架橋および非架橋アシル白金―マンガン二核錯体によるチエタンの開環反応機構2012

    • Author(s)
      尾田健太、趙霜、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      日吉(神奈川)
    • Related Report
      2011 Research-status Report
  • [Presentation] Chemoselective Oxidative Coupling Reactions by Ru(0) Complex2011

    • Author(s)
      M. Hirano
    • Organizer
      The 14th Asian Chemical Congress(招待講演)
    • Place of Presentation
      バンコク(タイ)
    • Related Report
      2011 Research-status Report
  • [Presentation] Chemoselective Cross Dimerization between Conjugate Diene and Conjugate Carbonyl Compound by Ruthenium(0) Complex2011

    • Author(s)
      M. Hirnao, Y. Arai, N. Komine, and S. Komiya
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋(愛知)
    • Related Report
      2011 Research-status Report
  • [Presentation] Synthesis and Intramolecular sp3 C-H Bond Cleavage Reaction of Bis(2,6-dimethylbenzenthiolato)palladium(II) Complex2011

    • Author(s)
      Y. Hara, S. Tatesawa, N. Komine, M. Hirano, and S. Komiya
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋(愛知)
    • Related Report
      2011 Research-status Report
  • [Presentation] (オルトアルキル置換フェノキソ)ルテニウム(II)錯体の分子内sp3 C-H結合の切断反応2011

    • Author(s)
      柳澤泰斗、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      第61回錯体化学討論会
    • Place of Presentation
      岡山(岡山)
    • Related Report
      2011 Research-status Report
  • [Presentation] ルテニウム(0)錯体上での異種共役ジエンの共二量化反応2011

    • Author(s)
      井上晴香、小峰伸之、平野雅文、 小宮三四郎
    • Organizer
      第61回錯体化学討論会
    • Place of Presentation
      岡山(岡山)
    • Related Report
      2011 Research-status Report
  • [Presentation] 撹拌により位置選択性が制御される水/ヘキサン二相系アリル化錯体触媒反応2011

    • Author(s)
      齋藤健史、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      第61回錯体化学討論会
    • Place of Presentation
      岡山(岡山)
    • Related Report
      2011 Research-status Report
  • [Presentation] 単色可視光により促進されるジメチルアリール白金-遷移金属ヘテロ二核錯体の有機基移動反応2011

    • Author(s)
      小田切達也、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      第61回錯体化学討論会
    • Place of Presentation
      岡山(岡山)
    • Related Report
      2011 Research-status Report
  • [Presentation] 0価ルテニウム錯体触媒による共役化合物の化学、位置およびジアス テレオ選択的カップリング反応2011

    • Author(s)
      平野雅文
    • Organizer
      第108回触媒討論会(招待講演)
    • Place of Presentation
      北見(北海道)
    • Related Report
      2011 Research-status Report
  • [Presentation] パラジウム(0)/ホスファイト系錯体触媒によるアセチレンジカルボン酸ジメチルへの...2011

    • Author(s)
      伊藤 涼、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      第108回触媒討論会
    • Place of Presentation
      北見(北海道)
    • Related Report
      2011 Research-status Report
  • [Presentation] ルテニウム(0)錯体を触媒とするメタクリル酸メチルとジヒドロフランの化学,位置および...2011

    • Author(s)
      広井結希、小峰伸之、平野雅文、小宮三四郎
    • Organizer
      第108回触媒討論会
    • Place of Presentation
      北見(北海道)
    • Related Report
      2011 Research-status Report
  • [Presentation] Carbon-Hydrogen Bond Cleavage Reaction in Four-Coordinate (2,6-Dimethylbenzenethiolato)platinum(II) Complexes. Dramatic Acceleration by Thiolato Hydrogen Acceptor2011

    • Author(s)
      M. Hirano, S. Tatesawa, N. Komine, and S. Komiya
    • Organizer
      1st International Symposium on Molecular Activation
    • Place of Presentation
      淡路(兵庫)
    • Related Report
      2011 Research-status Report
  • [Presentation] Dramatic Acceleration Effect by Hydrogen Acceptor on Internal sp3 Carbon-Hydrogen Bond Cleavage Reaction in Platinum(II) Complexes2011

    • Author(s)
      M. Hirano, S. Tatesawa, N. Komine, and S. Komiya
    • Organizer
      International Symposium on Catatalysis and Fine Chemicals 2011
    • Place of Presentation
      奈良(奈良)
    • Related Report
      2011 Research-status Report
  • [Presentation] Chemoselective Cross Dimerization between Conjugated Diene and Conjugated Carbonyl Compound by Ruthenium(0) Complex2011

    • Author(s)
      Y. Arai, N. Komine, M. Hirano, and S. Komiya
    • Organizer
      International Symposium on Catatalysis and Fine Chemicals 2011
    • Place of Presentation
      奈良(奈良)
    • Related Report
      2011 Research-status Report
  • [Presentation] Cis-selective Addition of Tungsten Hydride to Dimethyl Acetylenedicarboxylate Promoted by Palladium(0)/phosphite Complex Catalyst2011

    • Author(s)
      R. Ito, N. Komine, M. Hirano, and S. Komiya
    • Organizer
      International Symposium on Catatalysis and Fine Chemicals 2011
    • Place of Presentation
      奈良(奈良)
    • Related Report
      2011 Research-status Report
  • [Presentation] Intramolecular sp3 C-H Bond Cleavage Reaction of (ortho-Alkyl substituted phenoxo)ruthenium(II) Complex2011

    • Author(s)
      Y. Yanagisawa, N. Komine, M. Hirano, and S. Komiya
    • Organizer
      International Symposium on Catatalysis and Fine Chemicals 2011
    • Place of Presentation
      奈良(奈良)
    • Related Report
      2011 Research-status Report
  • [Presentation] Chemo-, Regio-, Diastereo- and Enantioselective Coupling of Substituted Alkenes by Ru(0)

    • Author(s)
      Masafumi Hirano
    • Organizer
      Minisymposium on Design of Efficient Molecular Catalysis for Environmental Benigh Chemical Process and Materials
    • Place of Presentation
      首都大学東京
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Remarks]

    • URL

      http://www.tuat.ac.jp/~hirano/kohrc/

    • Related Report
      2011 Research-status Report
  • [Patent(Industrial Property Rights)] 触媒前駆体および不斉鎖状化合物の合成方法2013

    • Inventor(s)
      平野雅文、小峰伸之、小宮三四郎
    • Industrial Property Rights Holder
      東京農工大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2013-028947
    • Filing Date
      2013-02-18
    • Related Report
      2012 Research-status Report

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Published: 2011-08-05   Modified: 2019-07-29  

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