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Development of a versatile catalytic system using NHC-stabilized monovalent nickel complexes

Research Project

Project/Area Number 25410123
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionFukuoka University

Principal Investigator

Matsubara Kouki  福岡大学, 理学部, 教授 (00294984)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2015: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2014: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Fiscal Year 2013: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Keywords錯体・有機金属触媒 / 有機ニッケル触媒 / クロスカップリング反応 / アミノ化反応 / 触媒反応 / ニッケル / 均一系触媒 / クロスカップリング / 多核クラスター / ニッケル1価錯体 / N-ヘテロ環状カルベン / 触媒的アミノ化反応 / 反応機構 / ヒドロアリール化反応 / N-ヘテロ環状カルベン / Suzukiカップリング反応
Outline of Final Research Achievements

Herein, NHC(N-heterocyclic carbene)-stabilized monovalent nickel complexes were systematically designed and prepared. The obtained complexes were applied to catalysts in the several cross-coupling reactions.
Several nickel(I) NHC complexes were synthesized in the presence of some phosphines, bisphosphines, pyridine and bipyridine. These compounds showed characteristic nature derived by the paramagnetic nickel(I) center. Applications using these complexes for several catalytic cross-coupling reactions of aryl halides as catalysts are also given. Particularly, intermediary nickel(I) amide complexes were successfully isolated. Moreover, it was revealed that these intermediates easily react with aryl halides to form the corresponding triarylamines as the cross-coupling products.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (33 results)

All 2016 2015 2014 2013 Other

All Int'l Joint Research (1 results) Journal Article (6 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 5 results,  Open Access: 1 results,  Acknowledgement Compliant: 2 results) Presentation (25 results) (of which Int'l Joint Research: 7 results) Remarks (1 results)

  • [Int'l Joint Research] Technische Universitat Wien(Austria)

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Bimetallic Cu(I) complex with a pyridine-bridged bis(1,2,3-triazole-5-ylidene) ligand2016

    • Author(s)
      Haruka Iwasaki, Yuta Teshima, Yuji Yamada, Ryuta Ishikawa, Yuji Koga and Kouki Matsubara
    • Journal Title

      Dalton Transactions

      Volume: 45 Issue: 13 Pages: 5713-5719

    • DOI

      10.1039/c6dt00008h

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Isolation and Structures of 1,2,3-Triazole-Derived Mesoionic Biscarbenes with Bulky Aromatic Groups2016

    • Author(s)
      Haruka Iwasaki, Yuji Yamada, Ryuta Ishikawa, Yuji Koga and Kouki Matsubara
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 9 Issue: 9 Pages: 1651-1654

    • DOI

      10.1002/ejoc.201501626

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis and Structure of Homoleptic Iron Complex Bearing Pincer-Type 1,2,3-Triazol-5-ylidene2016

    • Author(s)
      Haruka Iwasaki, Yuji Koga, Kouki Matsubara
    • Journal Title

      Organic Chemistry Current Research

      Volume: S6 Issue: S6 Pages: 1-5

    • DOI

      10.4172/2161-0401.s6-001

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Aluminum Complex Initiated Copolymerization of Lactones and DL-Lactide to Form Crystalline Gradient Block Copolymers Containing Stereoblock Lactyl Chains2016

    • Author(s)
      Kouki Matsubara, Kiyoka Eda, Yuki Ikutake, Misato Dan, Nao Tanizaki, Yuji Koga, and Munehisa Yasuniwa
    • Journal Title

      Journal of Polymer Science Part A: Polymer Chemistry

      Volume: 54 Issue: 16 Pages: 2536-2544

    • DOI

      10.1002/pola.28131

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 55.かさ高いN-ヘテロ環状カルベンをもつニッケル錯体触媒の開発とクロスカップリング反応への応用2014

    • Author(s)
      松原公紀
    • Journal Title

      有機合成化学協会誌

      Volume: 72 Pages: 1110-1119

    • Related Report
      2014 Research-status Report
    • Acknowledgement Compliant
  • [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
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] Buchwald-hartwig Amination of Aryl Halides Catalyzed by Ni(I) Complexes and Studies on the Reaction Mechanism2016

    • Author(s)
      Takahiro Inatomi, Yuji Koga, Kouki Matsubara
    • Organizer
      27th International Conference of Organometallic Chemistry
    • Place of Presentation
      Merborne Exhibition and Convention Center
    • Year and Date
      2016-07-17
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Tridentate 1,2,3-Triazol-5-Ylidene Complexes of Iron, Nickel and Copper2016

    • Author(s)
      Kouki Matsubara, Haruka Iwasaki, Yuta Teshima, Ayame Tajiri, Yuji Koga
    • Organizer
      27th International Conference of Organometallic Chemistry
    • Place of Presentation
      Merborne Exhibition and Convention Center
    • Year and Date
      2016-07-17
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 1,2,3-triazol-5-ylideneを配位子とする銅(I)2核錯体の合成と触媒反応への応用2016

    • Author(s)
      手嶋裕太、田尻菖、岩崎春香、古賀裕二、松原公紀
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 三座のメソイオン性カルベンを持つニッケル錯体の合成と反応2016

    • Author(s)
      田尻菖、手嶋裕太、岩崎春香、古賀裕二、松原公紀
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] コバルト錯体によるビスピナコールボランを用いたアルケン類の位置選択的ヒドロホウ素化反応2016

    • Author(s)
      角祥伍、古賀裕二、松原公紀
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Dinickel(I) complexes bearing bulky NHC ligand as catalysts in the Kumada-Tamao-Corriu coupling of aryl halides2015

    • Author(s)
      K. Matsubara, T. Inatomi, K. Nonaka, Y. Koga
    • Organizer
      Pacifichem2015
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-15 – 2015-12-20
    • Related Report
      2014 Research-status Report
  • [Presentation] Buchwald-Hartwig Amination of Aryl Halides Catalyzed by Ni(I) Complexes and Studies on the Reaction Mechanism2015

    • Author(s)
      Takahiro Inatomi, Yuji Koga, Kouki Matsubara
    • Organizer
      PACIFICHEM2015
    • Place of Presentation
      Hawaiian Convention Center
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Luminescence of Sterically Regulated Iridium Complexes2015

    • Author(s)
      Yuji Koga, Kouki Matsubara
    • Organizer
      PACIFICHEM2015
    • Place of Presentation
      Hawaiian Convention Center
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Dinickel(I) Complexes Bearing Bulky NHC Ligand as Catalysts in the Kumada-Tamao-Corriu Coupling of Aryl Halides2015

    • Author(s)
      Kouki Matsubara, Yuji Koga, Keita Nonaka, Takahiro Inatomi
    • Organizer
      PACIFICHEM2015
    • Place of Presentation
      Hawaiian Convention Center
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Buchwald-Hartwig Amination of Biarylamines Catalyzed by Ni(I) Complexes and Studies on the Reaction Mechanism2015

    • Author(s)
      Takahiro Inatomi, Yuji Koga, Kouki Matsubara
    • Organizer
      13th International Kyoto Conference of Organic Chemistry
    • Place of Presentation
      リーガロイヤルホテル京都
    • Year and Date
      2015-11-09
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Catalytic Hydroarylation Reaction of Alkenes Using Aryl Boronic Acid Ester2015

    • Author(s)
      Keita Nonaka, Yuji Koga, Kouki Matsubara
    • Organizer
      13th International Kyoto Conference of Organic Chemistry
    • Place of Presentation
      リーガロイヤルホテル京都
    • Year and Date
      2015-11-09
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] メソイオン性カルベン配位子を有するpincer型銅1価錯体の合成と反応2015

    • Author(s)
      手嶋裕太、岩崎春香、古賀裕二、松原公紀
    • Organizer
      第65回錯体化学討論会
    • Place of Presentation
      奈良女子大学
    • Year and Date
      2015-09-21
    • Related Report
      2015 Annual Research Report
  • [Presentation] かさ高いNHC配位子を有するコバルト錯体によるアルケンの触媒的ヒドロホウ素化反応2015

    • Author(s)
      角祥伍、古賀裕二、松原公紀
    • Organizer
      第65回錯体化学討論会
    • Place of Presentation
      奈良女子大学
    • Year and Date
      2015-09-21
    • Related Report
      2015 Annual Research Report
  • [Presentation] A Mechanistic Study in Buchwald-Hartwig Amination Catalyzed Ni(I) complexes bearing 2e donor ligands2015

    • Author(s)
      稲富貴裕、古賀裕二、松原公紀
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学千里山キャンパス
    • Year and Date
      2015-09-07
    • Related Report
      2015 Annual Research Report
  • [Presentation] Hydroarylation Reaction of Alkene by the Nickel Catalyst Using the Aryl Boronic Acid Ester2015

    • Author(s)
      野中恵太、古賀裕二、松原公紀
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学千里山キャンパス
    • Year and Date
      2015-09-07
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthesis and Behavior of Iron Complexes Bearing Tridentate 1,2,3-Triazole-ylidene2015

    • Author(s)
      岩崎春香、古賀裕二、松原公紀
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学千里山キャンパス
    • Year and Date
      2015-09-07
    • Related Report
      2015 Annual Research Report
  • [Presentation] 単核ニッケル1価錯体によるハロゲン化アリールの触媒的アミノ化反応及び反応機構研究2015

    • Author(s)
      稲富貴裕、古賀裕二、松原公紀
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] Monovalent Nickel Complexes as Catalysts in the Cross-Coupling Reactions2014

    • Author(s)
      K. Matsubara, T. Inatomi, S. Tazaki, H. Iwasaki, Y. Koga
    • Organizer
      The 2nd International Conference on Organometallics and Catalysis
    • Place of Presentation
      東大寺文化センター
    • Year and Date
      2014-10-26 – 2014-10-29
    • Related Report
      2014 Research-status Report
  • [Presentation] ニッケル触媒を用いたアルケンのヒドロアリール化反応2014

    • Author(s)
      野中恵太、古賀裕二、松原公紀
    • Organizer
      第114回触媒討論会
    • Place of Presentation
      広島大学東広島キャンパス
    • Year and Date
      2014-09-25 – 2014-09-27
    • Related Report
      2014 Research-status Report
  • [Presentation] コバルトNHC錯体を触媒とする不飽和炭化水素のヒドロホウ素化反応2014

    • Author(s)
      松原公紀、三浦敦美、角祥吾、古賀裕二
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学病院キャンパス
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Research-status Report
  • [Presentation] Cobalt-Catalyzed Hydroboration of Unsaturated Hydrocarbons Using Pinacolborane2014

    • Author(s)
      K. Matsubara, A. Miura, H. Iwasaki, Y. Koga
    • Organizer
      International Conference of Organometallic Chemistry 2014
    • Place of Presentation
      ロイトン札幌ホテル
    • Year and Date
      2014-07-14 – 2014-07-18
    • Related Report
      2014 Research-status Report
  • [Presentation] Ni(I)錯体を用いたビアリールアミン類のN-アリール化反応2014

    • Author(s)
      稲富貴裕、古賀裕二、松原公紀
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] ニッケル1価カルベン錯体の合成とSuzukiカップリングへの適用2014

    • Author(s)
      田崎冴子、古賀裕二、松原公紀
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] Cobalt-Catalyzed Hydroboration of Unsaturated Hydrocarbons Using Pinacolborane2014

    • Author(s)
      K. MATSUBARA, A. MIURA, H. IWASAKI, Y. KOGA
    • Organizer
      International Conference of Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌ホテル
    • Related Report
      2013 Research-status Report
  • [Presentation] Nickel(I) Complexes Bearing Various 2e-Donor Ligands for Catalytic Application2013

    • Author(s)
      Kouki Matsubara, Yukino Fukahori, Haruka Iwasaki, and Yuji Koga
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Research-status Report
  • [Remarks] 福岡大学研究者情報

    • URL

      http://resweb2.jhk.adm.fukuoka-u.ac.jp/FukuokaUnivHtml/info/4016/R107J.html

    • Related Report
      2015 Annual Research Report

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Published: 2014-07-25   Modified: 2019-07-29  

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