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Irradiation-Responsive Ligands for Efficient Iron-Catalysis

Research Project

Project/Area Number 17K14480
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

Shang Rui  東京大学, 大学院理学系研究科(理学部), 特任講師 (50793212)

Project Period (FY) 2017-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2018: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2017: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords鉄触媒 / 炭素-水素活性化 / 炭素-炭素結合 / 選択率 / 有機エレクトロニクス材料 / iron / C-H activation / cross coupling / iron-catalyzed / cyclization / conjugated pi-molecule / thiophene / 触媒設計・反応
Outline of Final Research Achievements

In this study, we developed a Fe-catalyzed method to convert stable arene C-H bonds, which are ubiquitous components of organic molecules, into carbon-carbon bonds in one step under mild conditions with high selectivity. From the viewpoint of sustainability, catalysts for organic synthesis using "ubiquitous elements" is desired, and it is most desirable to develop synthetic methods that use iron, which is the most abundant metal in earth. In this research, a simple, inexpensive, low toxic Fe-catalyzed synthetic method was developed to selectively cross-couple two arene C-H bonds with 100% selectivity. The high selectivity allows facile synthesis of organic electronic materials in a low cost and straightforward manner. This result provide a new way to synthesize valuable molecules of materials interest without using expensive and toxic metal catalyst that raising sustainability and environment issues, and will be beneficial for the future sustainable development of human society.

Academic Significance and Societal Importance of the Research Achievements

そこで今回我々は,鉄の触媒作用に着目し,等量の基質の存在下,両基質の炭素-水素結合を切断し,効率的に炭素-炭素結合を生成する反応の開発に成功した.本成果は恒星内元素合成により宇宙に普遍的に存在する鉄を触媒として用い,自然界に豊富に存在する有機化合物から少工程数・低コストで有用な有機化合物を合成するという究極的な目標達成の先駆けであり,環境負荷の高い金属触媒に頼る化学反応から脱却し,有用な有機化合物を提供することで人類の持続的発展を可能にすることが期待される.

Report

(3 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • Research Products

    (17 results)

All 2019 2018 Other

All Journal Article (2 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 2 results) Presentation (9 results) (of which Int'l Joint Research: 4 results) Remarks (5 results) Funded Workshop (1 results)

  • [Journal Article] Homocoupling-free iron-catalysed twofold C-H activation/cross-couplings of aromatics via transient connection of reactants2019

    • Author(s)
      Takahiro Doba, Tatsuaki Matsubara, Laurean Ilies, Rui Shang, Eiichi Nakamura
    • Journal Title

      Nature Catalysis

      Volume: 2 Issue: 5 Pages: 400-406

    • DOI

      10.1038/s41929-019-0245-3

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Disodium Benzodipyrrole Sulfonate as Neutral Hole-Transporting Materials for Perovskite Solar Cells2018

    • Author(s)
      Rui Shang*, Zhongmin Zhou, Hiroki Nishioka, Henry Halim, Shunsuke Furukawa, Izuru Takei, Naoya Ninomiya, and Eiichi Nakamura
    • Journal Title

      Journal of the American Chemical Society

      Volume: 140 Issue: 15 Pages: 5018-5022

    • DOI

      10.1021/jacs.8b01783

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] Synthetic Development of Organic Materials for Perovskite Solar Cell Applications2019

    • Author(s)
      Rui Shang and Eiichi Nakamura
    • Organizer
      The 99th CSJ Annual Meeting
    • Related Report
      2018 Annual Research Report
  • [Presentation] Irradiation-excited Palladium-catalysis through Blending Radical and Organometallic Reactivity2018

    • Author(s)
      Rui Shang
    • Organizer
      Beilstein Organic Chemistry Symposium 2018:Photoredox Catalysis for Novel Organic Reactions
    • Related Report
      2018 Annual Research Report
  • [Presentation] Benzodipyrrole Sulfonate Salts as Neutral Dopant-Free Hole-transporting Materials for Perovskite Solar Cells2018

    • Author(s)
      Rui Shang
    • Organizer
      The China-Japan Workshop for Innovations in Molecular Science and Technology
    • Related Report
      2018 Annual Research Report
  • [Presentation] Hybrid Benzodipyrrole Sulfonate Salt Materials in Perovskite Solar Cell Application2018

    • Author(s)
      Rui Shang, Zhongmin Zhou, Hiroki Nishioka, Henry Halim, Shunsuke Furukawa, and Eiichi Nakamura
    • Organizer
      The 29th Japan Symposium on Physical Organic Chemistry
    • Related Report
      2018 Annual Research Report
  • [Presentation] Hybrid Benzodipyrrole Sulfonate Salt Materials in Perovskite Solar Cell Applications2018

    • Author(s)
      Rui Shang and Eiichi Nakamura
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-14)
    • Related Report
      2018 Annual Research Report
  • [Presentation] Benzo[1,2-b:4,5-b]dipyrrole Sulfonate Salts as Neutral Dopant-Free Hole-transporting Materials for Highly Efficient and Stable Perovskite Solar Cells2018

    • Author(s)
      R. Shang(東大理), Z. Zhou(東大理), H. Nishioka(東大理), E. Nakamur(東大理)
    • Organizer
      International Symposium on Energy Science and Technology 2018, OIST, Okinawa, 2018/1/23
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Disodium Benzodipyrrole Sulfonate as Neutral Dopant-Free Hole-transporting Materials for Perovskite Solar Cells2018

    • Author(s)
      R. Shang(東大理), Z. Zhou(東大理), H. Nishioka(東大理), H. Halim(東大理), S. Furukawa(東大理), E. Nakamura(東大理)
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Glycine-HCl Modulated Growth of Oriented Lead Perovskite Crystals for Efficient Solar Cells2018

    • Author(s)
      Z. Qiang(東大理), H. Halim(東大理), R. Shang(東大理), E. Nakamura(東大理)
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Benzo[1,2-b:4,5-b]dipyrrole Sulfonate Salts as Neutral Dopant-Free Hole-transporting Materials for Highly Efficient and Stable Perovskite Solar Cells2018

    • Author(s)
      R. Shang(東大理), Z. Zhou(東大理), H. Nishioka(東大理), E. Nakamur(東大理)
    • Organizer
      International Symposium on Supramolecular Chemistry & Functional Materials 2018 (CEMSupra 2018)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Remarks] Two stories of iron

    • URL

      https://chemistrycommunity.nature.com/users/209773-eiichi-nakamura/posts/46018-two-stories-of-iron

    • Related Report
      2018 Annual Research Report
  • [Remarks] Simplified synthesis

    • URL

      https://www.eurekalert.org/pub_releases/2019-03/uot-ss032719.php

    • Related Report
      2018 Annual Research Report
  • [Remarks] Researchers simplify organic synthesis

    • URL

      https://www.alphagalileo.org/en-gb/Item-Display/ItemId/177123

    • Related Report
      2018 Annual Research Report
  • [Remarks] 鉄を触媒に異なる二つの炭素水素結合を切断し効率よく炭素炭素結合を生成する化学反応の開発に成功

    • URL

      https://www.nikkei.com/article/DGXLRSP505827_V20C19A3000000/

    • Related Report
      2018 Annual Research Report
  • [Remarks] 鉄を触媒に異なる二つの炭素水素結合を切断し効率よく炭素炭素結合を生成する化学反応の開発に成功

    • URL

      http://www.s.u-tokyo.ac.jp/ja/press/2019/6321/

    • Related Report
      2018 Annual Research Report
  • [Funded Workshop] International Symposium on Innovative Molecular Technology (ISIMT 2019) (in University of Tokyo, Japan)2019

    • Related Report
      2018 Annual Research Report

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Published: 2017-04-28   Modified: 2020-03-30  

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