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Development of Aromatic C-H Functionalization Triggered by Cation-pi Interaction

Research Project

Project/Area Number 15K17854
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionKyoto University

Principal Investigator

Iwamoto Takahiro  京都大学, 化学研究所, 特定助教 (50735355)

Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2016: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2015: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
KeywordsC-H官能基化 / 遷移金属触媒 / カチオン-π相互作用
Outline of Final Research Achievements

Selective C-H functionalization of simple arenes with no directing group still remains challenges. Catalytic system utilizing substrate-ligand interaction is a powerful approach to exhibit excellent reactivity and selectivity. In the previous reports, substrate-ligand interactions are limited to hydrogen bond, pi-stacking or acid-base interaction. Therefore substrates require some functional groups. For C-H functionalization of simple arene, I herein examined cation-pi interaction between arene substrate and ligand.
I succeeded in preparing a variety of ligands having diverse linkers. Catalytic activity of these ligands was next examined in several C-H functionalization of benzene, while reactions hardly proceeded in all cases. NMR study indicated that activation ability of the ligands was little for accelerating the C-H activation process. However, during these reaction screening, novel C-H functionalization of amine was discovered.

Report

(3 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • Research Products

    (7 results)

All 2016 2015

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Open Access: 2 results,  Acknowledgement Compliant: 1 results) Presentation (4 results) (of which Int'l Joint Research: 2 results)

  • [Journal Article] ONO-Pincer Ruthenium Complex-Bound Norvaline for Efficient Catalytic Oxydation of Methoxybenzenes with Hydrogen Peroxide2016

    • Author(s)
      R. Yoshida, K. Isozaki,* T. Yokoi, N. Yasuda, K. Sadakane, T. Iwamoto, H. Takaya,* and M. Nakamura*
    • Journal Title

      Organic Biomolecular Chemistry

      Volume: 14 Issue: 31 Pages: 7468-7479

    • DOI

      10.1039/c6ob00969g

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Radical Ions of Cyclopyrenylene: Comparison of Spectral Proeperties with Cycloparaphenylene2015

    • Author(s)
      Fujitsuka, M.; Tojo, S.; Iwamoto, T.; Kayahara, E.; Yamago, S.; Majima, T.
    • Journal Title

      J. Phys. Chem. A

      Volume: 115 Issue: 18 Pages: 4136-4141

    • DOI

      10.1021/acs.jpca.5b01189

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Structural Investigation of Cycloparaphenylene-Fullerene Supramolecular Complexes Using Synchrotron Radiation and Theoretical Calculation2015

    • Author(s)
      岩本 貴寛, 高谷 光, 山子 茂
    • Journal Title

      Nihon Kessho Gakkaishi

      Volume: 57 Issue: 4 Pages: 239-244

    • DOI

      10.5940/jcrsj.57.239

    • NAID

      130005096001

    • ISSN
      0369-4585, 1884-5576
    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] アルキンの鉄触媒カルボホウ素化とカルボシリル化反応の開発2016

    • Author(s)
      岩本 貴寛・中川 尚久・西郡 達志・畠山 琢次・中村 正治
    • Organizer
      第63回有機金属化学討論会
    • Place of Presentation
      東京
    • Year and Date
      2016-09-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] Characterization of Solution-phase Organoiron Catalyst by in situ XAFS Analysis2016

    • Author(s)
      Takahiro Iwamoto
    • Organizer
      Characterization of 9th CaRLa Winter School 2016
    • Place of Presentation
      Heidelberg, Germany
    • Year and Date
      2016-02-21
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 鉄触媒によるアルキンのアンチ選択的カルボシリル化反応2015

    • Author(s)
      岩本貴寛
    • Organizer
      第108回有機合成シンポジウム2015年【秋】
    • Place of Presentation
      早稲田大学
    • Year and Date
      2015-11-15
    • Related Report
      2015 Research-status Report
  • [Presentation] Anti-Selective Iron-Catalyzed Carbosilylation of Alkynes2015

    • Author(s)
      Takahiro Iwamoto
    • Organizer
      Organometallic Chemistry Directed Towards Organic Synthesis
    • Place of Presentation
      Sitges, Spain
    • Year and Date
      2015-06-28
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research

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Published: 2015-04-16   Modified: 2018-03-22  

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