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Synthesis of Nitrogen-Containing Poly Aromatic Compounds via Iron-Catalyzed C-H Amination

Research Project

Project/Area Number 15K13695
Research Category

Grant-in-Aid for Challenging Exploratory Research

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

Principal Investigator

Nakamura Masaharu  京都大学, 化学研究所, 教授 (00282723)

Project Period (FY) 2015-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Keywords鉄触媒 / CH官能基化 / アミノ化 / 含窒素多環芳香族化合物 / 有機電子材料 / 正孔輸送材料
Outline of Final Research Achievements

We have developed noble inter- and intramolecular C-H amination reactions and synthesized a variety of substituted 5,10-dihydrophenazines by short-step and concise synthetic route based on the newly developed lamination reactions. The synthesis utilized industrially attractive iron-catalysts and can convert easily accessible diarylamines to the corresponding ortho-phenylenediamines and consequently dihydrophenazines in the presence of versatile oxidants and the iron catalysts. This new method enables high-yielding preparation of various dihydrophenazines which have not been easily synthesized by the existing method due to the difficulties in prefunctionalization of substrates.

Report

(2 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • Research Products

    (4 results)

All 2016 2015

All Journal Article (2 results) (of which Peer Reviewed: 1 results) Presentation (1 results) (of which Int'l Joint Research: 1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Synthesis of 2,7-Disubstituted 5,10-Diaryl-5,10-dihydrophenazines via Iron-catalyzed Intramolecular Ring-Closing C–H Amination2015

    • Author(s)
      Aoki, Y; Imayoshi, R; Hatakeyama,T; Takaya, H; Nakamura, M.
    • Journal Title

      HETEROCYCLES (Kuwajima Special Issue)

      Volume: 90 Issue: 2 Pages: 893-900

    • DOI

      10.3987/com-14-s(k)102

    • NAID

      120005567893

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 安価な『鉄触媒』を用いたクロスカップリング反応2015

    • Author(s)
      中村正治 青木雄真
    • Journal Title

      月刊マテリアルステージ

      Volume: 12月号 Pages: 59-66

    • Related Report
      2015 Annual Research Report
  • [Presentation] Iron-Catalyzed C–H Amination of Aniline Derivatives2015

    • Author(s)
      Masaharu Nakamura, Ryuji Imayoshi, Hikaru Takaya, Yuma Aoki, Takuji Hatakeyama
    • Organizer
      Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS) 18
    • Place of Presentation
      Sitges - Barcelona, Spain
    • Year and Date
      2015-06-28
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Patent(Industrial Property Rights)] 非対称ビス(1,2-ジアリールアミノ)ベンゼン類及びその製造方法2016

    • Inventor(s)
      中村正治,高谷光,畠山琢次,鈴木毅,今吉隆治,青木雄真,他
    • Industrial Property Rights Holder
      中村正治,高谷光,畠山琢次,鈴木毅,今吉隆治,青木雄真,他
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2016-046085
    • Filing Date
      2016-03-09
    • Related Report
      2015 Annual Research Report

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Published: 2015-04-16   Modified: 2017-05-10  

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