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Coordinatively Unsaturated Dinickel Complexes as Concerted Catalysts and Preparation of Usable Catalytic System

Research Project

Project/Area Number 22550104
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionFukuoka University

Principal Investigator

MATSUBARA Kouki  福岡大学, 理学部, 准教授 (00294984)

Co-Investigator(Kenkyū-buntansha) KOGA Yuji  福岡大学, 理学部, 助教 (60373148)
Co-Investigator(Renkei-kenkyūsha) WAKITA Hisanobu  福岡大学, 理学部, 教授 (50078581)
Project Period (FY) 2010 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2012: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2011: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Fiscal Year 2010: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywords錯体・有機金属触媒 / 有機ニッケル触媒 / ニッケル2核錯体 / ニッケル1価錯体 / 触媒反応 / Kumadaカップリング / 触媒的アミノ化 / トリアリールアミン合成 / ニッケル1価錯体 / 協奏的触媒作用 / 2核錯体 / Kumadaクロスカップリング / Buchwald-Hartwigアミン化 / 反応機構解明 / ハロゲン化アリール
Research Abstract

Clarification of detailed concerted mechanism in the catalytic cross-coupling reactions of aryl halides using monovalent dinickel(I) complex bearing N-heterocyclic carbene, and development of versatile catalytic process have been achieved. (1) First, dinickel(I) intermediary compounds were isolated and determined, and EXAFS and XANES spectra were recorded to determine the structure of them. (1) Mechanistic consideration revealed that a redox cycle between Ni(I)-Ni(I) and Ni(II)-Ni(II) is possible during the catalytic reactions. (2) Buchwald-Hartwig amination of aryl halides with less reactive biarylamines proceeds even at room temperature. (3) Stable and reactive catalyst precursors of nickel(I) are prepared.

Report

(4 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (39 results)

All 2013 2012 2011 2010 Other

All Journal Article (10 results) (of which Peer Reviewed: 10 results) Presentation (25 results) Book (2 results) Remarks (2 results)

  • [Journal Article] Synthesis and Structure of Cobalt(II) Iodide Bearing a Bulky NHC ligand and Catalytic Activation of Bromoalkanes2013

    • Author(s)
      K. Matsubara, A. Kumamoto, H. Yamamoto, Y. Koga, S. Kawata
    • Journal Title

      Journal of Organometallic Chemistry

      Volume: 727 Pages: 42-49

    • DOI

      10.1016/j.jorganchem.2012.12.025

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Cobalt(II) Complexes Bearing a Bulky N-Heterocyclic Carbene for Catalysis of Kumada-Tamao-Corriu Cross-CouplingReactions of Aryl Halides2012

    • Author(s)
      K. Matsubara, T. Sueyasu, M. Esaki, A. Kumamoto, S. Nagao, H. Yamamoto, Y. Koga, S. Kawata, and T. Matsumoto
    • Journal Title

      Eur. J. Inorg. Chem

      Volume: 2012 Issue: 18 Pages: 3079-3086

    • DOI

      10.1002/ejic.201200095

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Ring-Opening Polymerization of D,L-Lactide, Initiated by Aluminum Isopropoxides BearingTridentate Non-Chiral Schiff-Base Ligands2012

    • Author(s)
      K. Matsubara, C. Terata, H. Sekine, K. Yamatani, T. Harada, K. Eda, Y. Koga, M. Yasuniwa
    • Journal Title

      Journal of Polymer Science: Part A: Polymer Chemistry

      Volume: 50 Issue: 5 Pages: 957-966

    • DOI

      10.1002/pola.25851

    • Related Report
      2012 Annual Research Report 2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Monovalent Nickel Complex Bearing a Bulky N-Heterocyclic Carbene Catalyzes Buchwald-Hartwig Amination of Aryl Halides under Mild Conditions2011

    • Author(s)
      S. Nagao, T. Matsumoto, Y. Koga, K. Matsubara
    • Journal Title

      Chemistry Letters

      Volume: 40 Issue: 9 Pages: 1036-1038

    • DOI

      10.1246/cl.2011.1036

    • NAID

      10029522960

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Luminescent Properties of Phosphorescent Iridium and Platinum Complex Polymers, Which Were Applied to OLED Devices2011

    • Author(s)
      Y. Koga, M. Kamo, Y. Yamada, T. Matsumoto, K. Matsubara
    • Journal Title

      European Journal of Inorganic Chemistry

      Volume: 2011 Issue: 18 Pages: 2869-2878

    • DOI

      10.1002/ejic.201100055

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Structure, Ligand Dynamics, and Catalytic Activity of Cationic [Pd(η^3-allyl)(κ^2(E,N)-EN-chelate)]^+(E=P, O, S, Se) Complexes2011

    • Author(s)
      Bernhard Bichler, Luis F.Veiros, Ozgur Oztopcu, Michael Puchberger, Kurt Mereiter, Kouki Matsubara, Karl A.Kirchner
    • Journal Title

      Organometallics

      Volume: 30 Issue: 21 Pages: 5928-5942

    • DOI

      10.1021/om200766y

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Radical Polymerization of Styrene Derivatives Bearing N-free Amino Acid Side Chains, Synergic Effect of Chirality and Hydrogen Bonding for Stereoselective Polymerization2010

    • Author(s)
      K. Matsubara, Y. Koga
    • Journal Title

      Journal of PolymerScience: Part A: Polymer Chemistry

      Volume: 48 Issue: 23 Pages: 5593-5602

    • DOI

      10.1002/pola.24274

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] A New Aspect of Nickel-Catalyzed Grignard Cross-Coupling Reactions: Selective Synthesis, Structure, and Catalytic Behavior of a T-Shape Three-Coordinate Nickel(I) Chloride Bearing a Bulky NHC Ligand2010

    • Author(s)
      S. Miyazaki, Y. Koga, T. Matsumoto, K. Matsubara
    • Journal Title

      Chemical Communications

      Volume: 46 Issue: 11 Pages: 1932-1934

    • DOI

      10.1039/b924716e

    • ISSN
      1359-7345, 1364-548X
    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] A New Aspect of Nickel-Catalyzed Grignard Cross-Coupling Reactions : SelectiveSynthesis, Structure, and Catalytic Behavior of a T -Shape Three-Coordinate Nickel(I)Chloride Bearing a Bulky NHC Ligand2010

    • Author(s)
      S.Miyazaki, Y.Koga, T.Matsumoto, K.Matsubara
    • Journal Title

      Chemical Communications

      Volume: 46 Pages: 1932-1934

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Radical Polymerization of Styrene Derivatives Bearing N-free Amino Acid Side Chains, Synergic Effect of Chirality and Hydrogen Bonding for Stereoselective Polymerization2010

    • Author(s)
      K.Matsubara, A.Kurimaru, M.Yamanaka, T.Hirashima, Y.Onishi, E.Murakami, E.Kawachi, Y.koga, S.Ando
    • Journal Title

      Journal of Polymer Science: Part A: Polymer Chemistry

      Volume: 48 Pages: 5593-5602

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] 単座あるいは二座配位子を有するニッケル(I)錯体の合成、構造、および触媒活性2013

    • Author(s)
      深堀由季乃、古賀裕二、松原公紀
    • Organizer
      第93春季年会
    • Place of Presentation
      立命館大学草津キャンパス
    • Year and Date
      2013-03-25
    • Related Report
      2012 Final Research Report
  • [Presentation] 単座あるいは二座配位子を有するニッケル(I)錯体の合成、構造、および触媒活性2013

    • Author(s)
      松原公紀
    • Organizer
      日本化学会第 93 春季年会
    • Place of Presentation
      立命館大学草津キャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] ニッケル1価NHC錯体を触媒とするKumadaカップリング反応の反応挙動2012

    • Author(s)
      山本瞳、古賀裕二、松原公紀
    • 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
    • Year and Date
      2012-09-13
    • Related Report
      2012 Final Research Report
  • [Presentation] Dinickel(I) Catalysts Bearing Bulky NHC Ligand; Synthesis and Catalytic Behavior toward Cross-Coupling Reactions of Aryl Halides.2012

    • Author(s)
      K. Matsubara, H. Yamamoto, Y. Koga
    • Organizer
      XXV International Conference on Organometallic Chemistry.
    • Place of Presentation
      Lisbon, Portugal
    • Year and Date
      2012-09-03
    • Related Report
      2012 Final Research Report
  • [Presentation] ニッケル(I)二核錯体による触媒的グリニャールクロスカップリング反応における反応機構2012

    • Author(s)
      山本瞳、古賀裕二、松原公紀
    • Organizer
      錯体化学会第62回討論会
    • Place of Presentation
      富山大学五福キャンパス
    • Year and Date
      2012-05-22
    • Related Report
      2012 Annual Research Report 2012 Final Research Report
  • [Presentation] Dinickel(I)Complexes Bearing a Bulky N-Heterocyclic Carbene in Efficient Kumada-Tamao-Corriu Cross-Coupling Reactions: a Mechanistic Study.2012

    • Author(s)
      H. Yamamoto, Y. Koga, K. Matsubara
    • Organizer
      10thInternational Conference of Hetero AtomChemistry.
    • Place of Presentation
      Kyoto
    • Year and Date
      2012-05-22
    • Related Report
      2012 Final Research Report
  • [Presentation] Monovalent Nickel Mediated Efficient Buchwald-Hartwig Amination of Aryl Halides.2012

    • Author(s)
      K. Matsubara, S. Nagao, H. Yamamoto, Y. Koga
    • Organizer
      10th International Conference of Hetero Atom Chemistry
    • Place of Presentation
      Kyoto
    • Year and Date
      2012-05-22
    • Related Report
      2012 Final Research Report
  • [Presentation] 触媒的クロスカップリング反応におけるニッケル(I)二核錯体の機構解明2012

    • Author(s)
      山本瞳・宮崎智史・古賀裕二・松原公紀
    • Organizer
      第92日本化学会春季年会
    • Place of Presentation
      慶応義塾大学
    • Year and Date
      2012-03-28
    • Related Report
      2011 Annual Research Report
  • [Presentation] 触媒的クロスカップリング反応におけるニッケル(I)二核錯体の機構解明2012

    • Author(s)
      山本瞳、宮崎智史、古賀裕二、松原公紀
    • Organizer
      第92春季年会
    • Place of Presentation
      慶応大学日吉キャンパス
    • Year and Date
      2012-03-24
    • Related Report
      2012 Final Research Report
  • [Presentation] ニッケル1価NHC錯体を触媒とするKumadaカップリング反応の反応挙動2012

    • Author(s)
      松原公紀
    • 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 Annual Research Report
  • [Presentation] かさ高いNHC配位子を有するコバルト錯体の合成とGrignard試薬によるアリールおよびアルキルハライドの触媒的活性化2012

    • Author(s)
      松原公紀
    • 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 Annual Research Report
  • [Presentation] Dinickel(I) Catalysts Bearing Bulky NHC Ligand; Synthesis and Catalytic Behavior toward Cross-Coupling Reactions of Aryl Halides.2012

    • Author(s)
      K. Matsubara
    • Organizer
      XXV International Conference on Organometallic Chemistry
    • Place of Presentation
      Lisbon
    • Related Report
      2012 Annual Research Report
  • [Presentation] Dinickel(I) Complexes Bearing a Bulky N-Heterocyclic Carbene in Efficient Kumada-Tamao-Corriu Cross-Coupling Reactions: a Mechanistic Study2012

    • Author(s)
      K. Matsubara
    • Organizer
      10th International Conference of Hetero Atom Chemistry
    • Place of Presentation
      Kyoto
    • Related Report
      2012 Annual Research Report
  • [Presentation] Monovalent Nickel Mediated Efficient Buchwald-Hartwig Amination of Aryl Halides2012

    • Author(s)
      K. Matsubara
    • Organizer
      10th International Conference of Hetero Atom Chemistry
    • Place of Presentation
      Kyoto
    • Related Report
      2012 Annual Research Report
  • [Presentation] 有機ニッケル錯体の分子設計と触媒機構研究2011

    • Author(s)
      松原公紀
    • Organizer
      有機合成化学協会九州山口支部平成23年度支部各賞受賞講演会・記念講演会
    • Place of Presentation
      鹿児島大学(招待講演)
    • Year and Date
      2011-12-08
    • Related Report
      2011 Annual Research Report
  • [Presentation] かさ高いN-ヘテロ環状カルベンを有するコバルト2価錯体の合成・構造とクロスカップリング触媒活性2011

    • Author(s)
      松原公紀・末安司・江崎万里子・古賀裕二
    • Organizer
      第61回錯体化学討論会
    • Place of Presentation
      岡山理科大学
    • Year and Date
      2011-09-17
    • Related Report
      2011 Annual Research Report
  • [Presentation] 触媒的クロスカップリング反応におけるニッケル(I)二核錯体の挙動解明2011

    • Author(s)
      山本瞳・宮崎智史・古賀裕二・松原公紀
    • Organizer
      第61回錯体化学討論会
    • Place of Presentation
      岡山理科大学
    • Year and Date
      2011-09-17
    • Related Report
      2011 Annual Research Report
  • [Presentation] クロスカップリング反応におけるニッケル1価2核錯体を経由する新しい反応機構2011

    • Author(s)
      松原公紀、山本瞳、長尾慎哉、古賀裕二
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2011-09-07
    • Related Report
      2012 Final Research Report
  • [Presentation] New Aspects of Bimetallic Systems in the Nickel(I)-Catalyzed Kumada-Tamao-Corriu Cross Coupling of Aryl Halides2011

    • Author(s)
      松原公紀・長尾慎哉・山本瞳・古賀裕二
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2011-09-07
    • Related Report
      2011 Annual Research Report
  • [Presentation] Buchwald-Hartwig Amination of Aryl Halides Under Mild Conditions Catalyzed by Nickel(I) N-Heterocyclic Carbene Complexes2011

    • Author(s)
      長尾慎哉・古賀裕二・松原公紀
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2011-09-07
    • Related Report
      2011 Annual Research Report
  • [Presentation] ニッケル1価NHC錯体の合成とハロゲン化アリールの触媒的アミノ化反応への適用2011

    • Author(s)
      長尾慎哉・松原公紀
    • Organizer
      有機合成化学協会九州山口支部第23回若手研究者のためのセミナー
    • Place of Presentation
      九州大学
    • Year and Date
      2011-08-27
    • Related Report
      2011 Annual Research Report
  • [Presentation] Cross-Coupling Reactions of Aryl Halides Catalyzed by Nickel Complexes.2011

    • Author(s)
      K. Matsubara
    • Organizer
      Symposium in Institute fur Angewante Chemie
    • Place of Presentation
      Technische Universitat Wien, Wien
    • Year and Date
      2011-03-30
    • Related Report
      2012 Final Research Report
  • [Presentation] かさ高いN-ヘテロ環状カルベン配位子をもつニッケル(I)二核錯体とハロゲン化アリールとの反応2011

    • Author(s)
      山本瞳・古賀裕二・松原公紀
    • Organizer
      第91日本化学会春季年会
    • Place of Presentation
      神奈川大学
    • Year and Date
      2011-03-26
    • Related Report
      2010 Annual Research Report
  • [Presentation] Monovalent Nickel Complex Bearing Bulky N-Heterocyclic Carbene Catalyzed Kumada Cross-Coupling Reactions.2010

    • Author(s)
      S. Nagao, Y. Koga, K. Matsubara
    • Organizer
      2010International Chemical Congress ofPacific Basin Societies
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-18
    • Related Report
      2012 Final Research Report
  • [Presentation] Ni(I)NHC錯体の合成、構造およびハロゲン化アリールの触媒的クロスカップリング2010

    • Author(s)
      長尾慎哉・古賀裕二・松原公紀
    • Organizer
      第60回錯体化学討論会
    • Place of Presentation
      大阪国際交流センター
    • Year and Date
      2010-09-28
    • Related Report
      2010 Annual Research Report
  • [Book] Synthesis and Luminescent Properties of Phosphorescent Iridium and Platinum Complex Polymers, Which Were Applied to OLED Devices2011

    • Author(s)
      Y. Koga, K. Matsubara
    • Publisher
      Organic Light Emitting Diode - Material
    • Related Report
      2012 Final Research Report
  • [Book] Organic Light Emitting Diode-Material, Process and Devices2011

    • Author(s)
      Yuji Koga, Kouki Matsubara
    • Total Pages
      20
    • Publisher
      InTech
    • Related Report
      2011 Annual Research Report
  • [Remarks] かさ高いカルベン配位子を持つニッケル分子触媒と触媒的クロスカップリング反応の開発

    • URL

      http://www.adm.fukuoka-u.ac.jp/fu844/home2/Ronso/Rigaku/S42-2/S4202_0133.pdf

    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://www.sc.fukuoka-u.ac.jp/~psc/kenkyu01.htm

    • Related Report
      2011 Annual Research Report

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Published: 2010-08-23   Modified: 2019-07-29  

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