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Development of Catalytic Reaction Mediated by Early Transition Metal via Sigma-bond Metathesis Reaction

Research Project

Project/Area Number 16H06934
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionOsaka University

Principal Investigator

Nagae Haruki  大阪大学, 基礎工学研究科, 助教 (40779005)

Project Period (FY) 2016-08-26 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
KeywordsC-H結合活性化 / 前周期遷移金属 / アミノアルキル化反応 / アミド錯体 / アルキル錯体 / 不斉反応 / 炭素-水素結合活性化 / 炭素―水素結合活性化
Outline of Final Research Achievements

The target of this research is development of catalytic C-H bond functionalization mediated by early transition metal complexes which show unique reactivity via σ-bond metathesis reaction. In 2016, I optimized reaction conditions, in which a combination of an trialkylyttrium complex and a bidentate ligand, N,N’-bis(2,6-diisopropylphenyl)ethane-1,2-diamido, showed the highest catalytic activity toward ortho C-H bond aminoalkylation reaction of 2-substituted pyridine derivatives. Based on this result, I am planning to screen chiral bidentate ligands to achieve chiral aminoalkylation reaction.

Report

(3 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Annual Research Report
  • Research Products

    (15 results)

All 2018 2017 2016 Other

All Int'l Joint Research (2 results) Journal Article (4 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 4 results,  Acknowledgement Compliant: 1 results) Presentation (9 results) (of which Int'l Joint Research: 8 results,  Invited: 1 results)

  • [Int'l Joint Research] ETH Zurich(スイス)

    • Related Report
      2017 Annual Research Report
  • [Int'l Joint Research] RWTH Aachen(Germany)

    • Related Report
      2017 Annual Research Report
  • [Journal Article] Lanthanide Complexes Supported by a Trizinc Crown Ether as Catalysts for Alternating Copolymerization of Epoxide and CO2: Telomerization Controlled by Carboxylate2018

    • Author(s)
      Haruki Nagae, Ryota Aoki, Shin-nosuke Akutagawa, Julian Kleemann, Risa Tagawa, Tobias Schindler, Gyeongshin Choi, Thomas P. Spaniol, Hayato Tsurugi, Jun Okuda and Kazushi Mashima
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 57 Issue: 9 Pages: 2492-2496

    • DOI

      10.1002/anie.201709218

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Silica-Supported Isolated Molybdenum Di-oxo Species: Formation and Activation with Organosilicon Agent for Olefin Metathesis2018

    • Author(s)
      Keishi Yamamoto, Ka Wing Chan, Victor Mougel, Haruki Nagae, Hayato Tsurugi, Olga V. Safonova, Kazushi Mashima, and Christophe Coperet
    • Journal Title

      Chem. Commun.

      Volume: 54 Issue: 32 Pages: 3989-3992

    • DOI

      10.1039/c8cc01876f

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Propargylic C(sp3)-H Bond Activation for Preparing η3-Propargyl/Allenyl Complexes of Yttrium2017

    • Author(s)
      Nagae Haruki、Kundu Abhinanda、Tsurugi Hayato、Mashima Kazushi
    • Journal Title

      Organometallics

      Volume: 36 Issue: 16 Pages: 3061-3067

    • DOI

      10.1021/acs.organomet.7b00395

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Arylimido-Bridged Dinuclear Ti(μ-NAr)2Ti Scaffold for Alkyne Insertion into ortho-C-H Bond of Arylimido Ligands2017

    • Author(s)
      Haruki Nagae, Wataru Hato, Kento Kawakita, Hayato Tsurugi, Kazushi Mashima
    • Journal Title

      Chemistry - A European Journal

      Volume: 23 Issue: 3 Pages: 586-596

    • DOI

      10.1002/chem.201603580

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Direct ortho-C-H bond aminoalkylation of pyridine derivatives catalyzed by yttrium complexes with diamido ligands2018

    • Author(s)
      Mariko Inoue, Abhinanda Kundu, Haruki Nagae, Hayato Tsurugi and Kazushi Mashima
    • Organizer
      Biotechnology and Chemistry for Green Growth
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Yttrium-amide complexes for direct C-H aminoalkylation of 2-substituted pyridine derivatives2017

    • Author(s)
      Kazushi Mashima, Abhinanda Kundu, Haruki Nagae and Hayato Tsurugi
    • Organizer
      XXVIII. Tade der Seltenen Erden-Terrae Rarae 2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 二座ジアミド配位子を有する希土類金属錯体を触媒としたピリジン誘導体のアミノアルキル化反応と反応メカニズムの解明2017

    • Author(s)
      長江 春樹,Abhinanda Kundu,劒 隼人,真島 和志
    • Organizer
      第33回希土類討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Direct aminomethylation for an ortho C-H bond of N-heteroaromatic compounds catalyzed by triamido complexes of group 3 metals2016

    • Author(s)
      Abhinanda Kundu, Haruki Nagae, Hayato Tsurugi, and Kazushi Mashima
    • Organizer
      Third International symposium on C-H activation
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] C-H bond activation of N-heteroaromatics catalyzed by group 3 metal complexes2016

    • Author(s)
      Kazushi Mashima, Haruki Nagae, Yu Shibata, and Hayato Tsurugi
    • Organizer
      Rare earth 2016 in Sapporo
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] C-H bond functionalization reaction mediated by rare-earth metal complexes2016

    • Author(s)
      Haruki Nagae
    • Organizer
      Pre-symposium of Rare Earths 2016
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Rare-earth metal catalyzed aminoalkylation reaction of ortho-C-H bonds in pyridines2016

    • Author(s)
      Haruki Nagae, Abhinanda Kundu, Hayato Tsurugi, and Kazushi Mashima
    • Organizer
      USA-Japan Joint Workshop on C-H Bond Activation
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Direct C-H aminoalkyaltion of 2-substituted pyridine derivatives catalyzed by yttrium catalysts with N,N'-diarylethylenediamido ligands2016

    • Author(s)
      Abhinanda Kundu, Haruki Nagae, Hayato Tsurugi, and Kazushi Mashima
    • Organizer
      JSPS Japanese-German Graduate Externship International Symposium, Aachen, Germany
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Direct aminomethylation for an ortho C-H bond of N-heteroaromatic compounds catalyzed by triamido complexes of group 3 metals2016

    • Author(s)
      Abhinanda Kundu, Haruki Nagae, Hayato Tsurugi, and Kazushi Mashima
    • Organizer
      International Symposium on C-O Activation
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research

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Published: 2016-09-02   Modified: 2022-08-19  

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