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Development of Photoredox technology

Research Project

Project/Area Number 19H02711
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionTokyo Institute of Technology

Principal Investigator

Akita Munetaka  東京工業大学, 科学技術創成研究院, 教授 (50167839)

Co-Investigator(Kenkyū-buntansha) 田中 裕也  東京工業大学, 科学技術創成研究院, 助教 (90700154)
Project Period (FY) 2019-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥17,420,000 (Direct Cost: ¥13,400,000、Indirect Cost: ¥4,020,000)
Fiscal Year 2021: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2020: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2019: ¥8,580,000 (Direct Cost: ¥6,600,000、Indirect Cost: ¥1,980,000)
Keywordsフォトレドックス触媒 / ラジカル反応 / フルオロアルキル化 / 可視光エネルギー有効利用 / 二官能基化化反応 / 不飽和炭化水素 / 超分子触媒 / フルオロアルキルラジカル / 可視光利用 / フォトレドックス触媒作用 / ラジカル / 有機フォトレドックス触媒 / 高還元力触媒
Outline of Research at the Start

フォトレドックス触媒反応は、太陽光を含む可視光照射のみで進行するグリーンな触媒反応系として近年注目を集めている。本研究では、フォトレドックス触媒の実効的かつ飛躍的発展を目的として、①新ラジカル前駆体、②強力還元系有機物触媒、③不斉合成、④実用的触媒反応系の開発を目標に定めて相互に関連させながら研究を進める。特に不斉合成は「ラジカル種による不斉合成」という普遍的なテーマにもつながっており、①、②の成果を活用した上で、温和な条件下でラジカル種を発生させることが可能な本系の特長を活かした反応設計をおこなって課題解決に挑戦する。

Outline of Final Research Achievements

Inoeder to strengthen synthetic organic chemistry based on photoredox catalysis studies have been carried out from the viewpoints of developments of (i) new radical precursors, (ii) strognly reducing organic catalysts, (iii) new reactions, and (iv) practical catalytic systems. The points (i) and (ii) are essential to attain (iii), and, as expected, we have succeeded in developments of generation of various organic radical from readily accessible precursors to lead to new reactions of unsaturated hydrocarbons, in particular, fluoroalkylation. The technique has become practical by using, for example, flow systems. Typically, we have developed green production systems of organic compounds under environmentally benign conditions similar to biological systems, i.e. visible light (including sunlight)-room temperature-in water.

Academic Significance and Societal Importance of the Research Achievements

環境・エネルギー問題の解決が標榜される中で太陽光を含む可視光エネルギーの有効利用が注目を集めており、その一手法として可視光フォトレドックス触媒作用が有機合成化学の領域では盛んに研究されている。そのような状況の中で、申請者は、パイオニアの一人としてこの領域を牽引してきたが、本研究では、さらにその有効性を高める観点から研究を進めた結果、フォトレドックス触媒研究のすそ野を広げて、アクセスを容易にするとともに、汎用性を広げてさらにこの領域を活性化するとともに、実用性の観点からもその有効性を高めることに大きく寄与した。

Report

(4 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Annual Research Report
  • 2019 Annual Research Report
  • Research Products

    (22 results)

All 2022 2021 2020 2019 Other

All Journal Article (11 results) (of which Peer Reviewed: 11 results) Presentation (9 results) (of which Int'l Joint Research: 5 results,  Invited: 9 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Assemblies of 1,4-Bis(diarylamino)naphthalene and Aromatic Amphiphiles: Highly Reducing Photoredox Catalysis in Water2022

    • Author(s)
      Yuki Hyodo, Keigo Takahashi, Youhei Chitose, Manabu Abe, Michito Yoshizawa, Takashi Koike, Munetaka Akita
    • Journal Title

      Synlett

      Volume: 33 Issue: 12 Pages: 1184-1188

    • DOI

      10.1055/a-1652-2707

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Simple generation of various α-monofluoroalkyl radicals by organic photoredox catalysis: modular synthesis of β-monofluoroketones2021

    • Author(s)
      Ryo Taniguchi, Naoki Noto, Seiya Tanaka, Keigo Takahashi, Sujan K. Sarkar, Ryoko Oyama, Manabu Abe, Takashi Koike, Munetaka Akita
    • Journal Title

      Chem. Commun.

      Volume: 57 Issue: 21 Pages: 2609-2611

    • DOI

      10.1039/d0cc08060h

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Modern Synthetic Strategies for One-Electron Injection2021

    • Author(s)
      T. Koike, M. Akita
    • Journal Title

      Trends in Chemistry

      Volume: 3 Issue: 5 Pages: 416-427

    • DOI

      10.1016/j.trechm.2021.02.006

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 可視光フォトレドックス分子触媒による新反応開発2021

    • Author(s)
      穐田宗隆
    • Journal Title

      触媒

      Volume: 63 Pages: 164-170

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Fluoroalkanesulfinate Salts as Dual Fluoroalkyl and SO2 Sources: Atom-Economical Fluoroalkyl-Sulfonylation of Alkenes and Alkynes by Photoredox Catalysis2020

    • Author(s)
      Tanaka Seiya、Nakayama Yoshiki、Konishi Yusuke、Koike Takashi、Akita Munetaka
    • Journal Title

      Organic Letters

      Volume: 22 Issue: 7 Pages: 2801-2805

    • DOI

      10.1021/acs.orglett.0c00789

    • Related Report
      2020 Annual Research Report 2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Energy transfer-driven regioselective synthesis of functionalized phenanthridines by visible-light Ir photocatalysis2020

    • Author(s)
      Matsushita Yuki、Ochi Rika、Tanaka Yuya、Koike Takashi、Akita Munetaka
    • Journal Title

      Organic Chemistry Frontiers

      Volume: 7 Issue: 10 Pages: 1243-1248

    • DOI

      10.1039/d0qo00271b

    • Related Report
      2020 Annual Research Report 2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Laser Flash Photolysis Studies on Radical Monofluoromethylation by (Diarylamino)naphthalene Photoredox Catalysis: Long Lifetime of the Excited State is Not Always a Requisite2020

    • Author(s)
      Noto Naoki、Takahashi Keigo、Goryo Shion、Takakado Akira、Iwata Koichi、Koike Takashi、Akita Munetaka
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 85 Issue: 20 Pages: 13220-13227

    • DOI

      10.1021/acs.joc.0c01999

    • Related Report
      2020 Annual Research Report 2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Transition Metal-Free Supramolecular Photoredox Catalysis in Water: A Phenoxazine Photocatalyst Encapsulated in V-Shaped Aromatic Amphiphiles2020

    • Author(s)
      N. Noto, Y. Hyodo, M. Yoshizawa, T. Koike, M. Akita
    • Journal Title

      ACS Catal.

      Volume: 10 Issue: 23 Pages: 14283-14289

    • DOI

      10.1021/acscatal.0c04221

    • Related Report
      2020 Annual Research Report 2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Visible-Light-Triggered Monofluoromethylation of Alkenes by Strongly Reducing 1,4-Bis(diphenylamino)naphthalene Photoredox Catalysis2019

    • Author(s)
      Noto Naoki、Koike Takashi、Akita Munetaka
    • Journal Title

      ACS Catalysis

      Volume: 9 Issue: 5 Pages: 4382-4387

    • DOI

      10.1021/acscatal.9b00473

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Keto-Difluoromethylation of Aromatic Alkenes by Photoredox Catalysis: Step-Economical Synthesis of α-CF2H-Substituted Ketones in Flow2019

    • Author(s)
      Yoshiki Nakayama, Gaku Ando, Manabu Abe, Takashi Koike, Munetaka Akita
    • Journal Title

      ACS Catalysis

      Volume: 9 Pages: 6555-6563

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Recent progress in photochemical radical di- and mono-fluoromethylation2019

    • Author(s)
      Koike Takashi、Akita Munetaka
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 17 Issue: 22 Pages: 5413-5419

    • DOI

      10.1039/c9ob00734b

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Presentation] フォトレドックス触媒反応:フルオロアルキル化反応と高還元力触媒の開発2021

    • Author(s)
      穐田宗隆
    • Organizer
      有機合成化学協会
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] Renaissance of Photoredox Catalysis: Organic Synthesis Driven by Visible Light2021

    • Author(s)
      穐田宗隆
    • Organizer
      光化学討論会
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] フォトレドックス触媒作用に基づいたフルオロアルキル化反応系の開発2021

    • Author(s)
      穐田宗隆
    • Organizer
      フッ素化学会
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] フォトレドックス触媒反応:可視光(太陽光)で駆動する有機反応2021

    • Author(s)
      穐田宗隆、小池隆司
    • Organizer
      電気化学会
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] Fluoroalkylation of Olefins by Highly Reducing Organic Photoredox Catalysts: Opposites of Fukuzumi Catalyst2019

    • Author(s)
      Munetaka Akita
    • Organizer
      9th Pacific Symposium on Radical Chemistry (PSRC-9)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Highly Reducing Organic Photoredox Catalaysts and Their Application to Fluoroalkylation of Olefins2019

    • Author(s)
      Munetaka Akita
    • Organizer
      XXI Mendeleev Congress on General and Applied Chemistry
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Fluoroalkylation of Olefins by Highly Reducing Organic Photoredox Catalysts2019

    • Author(s)
      Munetaka Akita
    • Organizer
      the International Conference "Catalysis and Organic Synthesis" (ICCOS-2019)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Fluoroalkylation of Olefins by Highly Reducing Organic Photoredox Catalysts2019

    • Author(s)
      Munetaka Akita
    • Organizer
      The 18th Asian Chemical Congress (18ACC)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Supramolecular photoredox catalysis in water2019

    • Author(s)
      Munetaka Akita
    • Organizer
      The 2nd NCTU Conference on Advanced Organic Synthesis (CAOS-2)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Remarks] 穐田研究室

    • URL

      http://www.res.titech.ac.jp/~smart/smartj_MA.html

    • Related Report
      2019 Annual Research Report
  • [Patent(Industrial Property Rights)] 高い還元力を有する芳香環光レドックス触媒2019

    • Inventor(s)
      13.小池隆司・納戸直木・谷口諒・高橋慶悟・穐田宗隆
    • Industrial Property Rights Holder
      13.小池隆司・納戸直木・谷口諒・高橋慶悟・穐田宗隆
    • Industrial Property Rights Type
      特許
    • Filing Date
      2019
    • Related Report
      2019 Annual Research Report

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Published: 2019-04-18   Modified: 2023-01-30  

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