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Development of the reactions with hydrogen based on hydride-accepting ability of organic cations

Research Project

Project/Area Number 25410108
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

SEINO Hidetake  秋田大学, 教育文化学部, 准教授 (50292751)

Co-Investigator(Renkei-kenkyūsha) YOSHIE Naoko  東京大学, 生産技術研究所, 教授 (20224678)
Project Period (FY) 2013-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords水素 / カチオン性複素環 / 錯体触媒 / 有機ヒドリド供与体 / ヒドロゲナーゼ / メタン生成 / 酸化還元反応 / 水素吸蔵
Outline of Final Research Achievements

Catalytic cleavage of hydrogen into proton and hydride followed by transfer of the hydride to cationic nitrogen-heterocycles was investigated. Organic products in this reaction system were stable under ambient conditions, but in the presence of catalysts could serve as organic hydride reagents to generate hydrogen gas via protonation or to reduce other organic molecules. One carbon unit was activated toward nucleophiles by composing a cationic heterocyclic system, and hydride transfer to this unit enabled advance of the reduction-level under mild conditions. This reaction is relevant to some steps in methanogenetic pathways utilizing hydrogen to reduce carbon dioxide with the aid of organic coenzymes.

Report

(5 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (14 results)

All 2017 2016 2015 2014 2013

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Acknowledgement Compliant: 3 results) Presentation (9 results) (of which Int'l Joint Research: 1 results,  Invited: 2 results)

  • [Journal Article] Structural determination, DFT calculation, and formation mechanism of ethyl 2-cyano-3-alkoxypent-2-enoates synthesized via Ru-mediated coupling reaction between α,β-unsaturated acetals and cyanoacetate2017

    • Author(s)
      Hidetake Seino, Takumi Kondo, Chihiro Mochizuki, Ken Tokunaga, Motowo Yamaguchi, Mitsunobu Sato
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 90 Issue: 1 Pages: 79-87

    • DOI

      10.1246/bcsj.20160279

    • NAID

      130005289871

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and Protonation of N‑Heterocyclic-Carbene-Supported Dinitrogen Complexes of Molybdenum(0)2015

    • Author(s)
      Yasuhiro Ohki, Keiya Aoyagi, Hidetake Seino
    • Journal Title

      Organometallics

      Volume: 34 Issue: 13 Pages: 3414-3420

    • DOI

      10.1021/acs.organomet.5b00391

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] N-Heterocyclic carbenes as supporting ligands in transition metal complexes of N22015

    • Author(s)
      Yasuhiro Ohki, Hidetake Seino
    • Journal Title

      Dalton Transactions

      Volume: 45 Issue: 3 Pages: 874-880

    • DOI

      10.1039/c5dt04298d

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] A molybdenum complex bearing a tetraphosphine ligand as a precursor for heterobimetallic complexes2014

    • Author(s)
      Ryoga Yasuda, Kentaro Iwasa, Fumiya Niikura, Hidetake Seino, and Yasushi Mizobe
    • Journal Title

      Dalton Transactions

      Volume: 43 Issue: 24 Pages: 9344-9355

    • DOI

      10.1039/c4dt00581c

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Linear Connection of Four Nitrile Molecules on the Tetraphosphine Complexes of Tungsten and Molybdenum2014

    • Author(s)
      Qi Xiu Dai, Hidetake Seino, and Yasushi Mizobe
    • Journal Title

      Organometallics

      Volume: 33 Issue: 13 Pages: 3652-3655

    • DOI

      10.1021/om500405f

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] メタン生成経路の補酵素テトラヒドロメタノプテリンの機能を模したC1ユニット水素化2016

    • Author(s)
      清野 秀岳,鈴木 颯,髙橋 和輝,畑澤匡広
    • Organizer
      第118回触媒討論会
    • Place of Presentation
      岩手大学
    • Year and Date
      2016-09-21
    • Related Report
      2016 Annual Research Report
  • [Presentation] Metal-catalyzed reactions of N,N'-disubstituted imidazolinium cations with hydrogen as functional models of hydrogenases in methanogenesis2015

    • Author(s)
      Hidetake Seino
    • Organizer
      2015 International Chemical Congress of Pacific Basin Society
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Metal-Mediated Reversible Reactions of 1,3-Disubstituted Imidazolinium Cations with Hydrogen as a Functional Model of [Fe]-Hydrogenase2014

    • Author(s)
      Hidetake Seino, Masahiro Hatazawa, Yoshihiro Hojo, Yasushi Mizobe, Naoko Yoshie, Hayate Suzuki
    • Organizer
      Vietnam Malaysia International Chemical Congress 2014
    • Place of Presentation
      Daewoo Hotel Hanoi, Hanoi, Vietnam
    • Year and Date
      2014-11-07 – 2014-11-09
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Reversible Reaction of 1,3-Disubstituted Imidazolinium Cations with Molecular Hydrogen as a Functional Model of [Fe]-Hydrogenase2014

    • Author(s)
      Hidetake Seino
    • Organizer
      ICOMC2014 Pre-Symposium in Sendai
    • Place of Presentation
      東北大学工学部センターホール
    • Year and Date
      2014-07-11
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Reversible Reactions of 1,3-Disubstituted Dihydroimidazolium Cations with Hydrogen Catalyzed by Transition Metal Complexes2013

    • Author(s)
      Hidetake Seino, Masahiro Hatazawa, Yoshihiro Hojo, Yasushi Mizobe, Naoko Yoshie
    • Organizer
      The 15th Asian Chemical Congress
    • Place of Presentation
      Singapore
    • Related Report
      2013 Research-status Report
  • [Presentation] 金属触媒を利用した水素分子からのヒドリド移動および逆反応の開発2013

    • Author(s)
      畑澤匡広・清野秀岳・吉江尚子
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      学習院大学(東京)
    • Related Report
      2013 Research-status Report
  • [Presentation] 遷移金属錯体触媒による1,3-二置換ジヒドロイミダゾリウムカチオンの水素化2013

    • Author(s)
      清野秀岳・畑澤匡弘・北條喜洋・溝部裕司・吉江尚子
    • Organizer
      第112回触媒討論会
    • Place of Presentation
      秋田大学(秋田)
    • Related Report
      2013 Research-status Report
  • [Presentation] Tetraphosphine Complexes of Palladium and Platinum2013

    • Author(s)
      Hidetake Seino, Ryoga Yasuda, Yasushi Mizobe
    • Organizer
      International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan
    • Place of Presentation
      東北大学(仙台)
    • Related Report
      2013 Research-status Report
  • [Presentation] Development of Reversible Hydrogenation-Dehydrogenation of Dihydroimidazolium2013

    • Author(s)
      Masahiro Hatazawa, Hidetake Seino, Naoko Yoshie
    • Organizer
      International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan
    • Place of Presentation
      東北大学(仙台)
    • Related Report
      2013 Research-status Report

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

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