Grant-in-Aid for Scientific Research on Innovative AreasPrecise Formation of a Catalyst Having a Specified Field for Use in Extremely Difficult Substrate Conversion Reactions

Takashi Koike » Japanese

Affiliation Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology
Position Assistant Professor
HP http://www.res.titech.ac.jp/~smart/smart_e.html
Speciality Organometallic Chemistry, Organic Synthesis
Keyword Photocatalysis, Organofluorine Compounds, Redox Reaction, Radical Reaction
Institute The Chemical Society of Japan, The Society of Synthetic Organic Chemistry Japan, Catalysis Society of Japan, Japan Society of Coordination Chemistry, The Society of Fluorine Chemistry Japan, The Japanese Photochemistry Association, Japanese Society for Chemical Biology

Abstract

Synthesis and Visible-Light-Induced Reaction of Photoredox Catalysts Bearing Extremely Electron-Withdrawing SF5 Group

Achievement

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Original papers

  • "Fluoroalkanesulfinate Salts as Dual Fluoroalkyl and SO2 Sources: Atom-Economical Fluoroalkyl-Sulfonylation of Alkenes and Alkynes by Photoredox Catalysis"
    Tanaka, S.; Nakayama, Y.; Konishi, Y.; *Koike, T.; *Akita, M.
    Organic Letters, 2020, 22, 2801-2805
  • "Keto-Difluoromethylation of Aromatic Alkenes by Photoredox Catalysis: Step-Economical Synthesis of α-CF2H-Substituted Ketones in Flow"
    Nakayama, Y.; Ando, G.; Abe, M.; *Koike, T.; *Akita, M.
    ACS Catalysis, 2019, 9, 6555-6563
  • "Visible Light-Triggered Monofluoromethylation of Alkenes by Strongly Reducing 1,4-Bis(diphenylamino)naphthalene Photoredox Catalysis"
    Noto, N.; *Koike, T.; *Akita, M.
    ACS Catalysis, 2019, 9, 4382-4387
  • "Photoredox Radical C-H Oxygenation of Aromatics with Aroyloxylutidinium Salts"
    Miyazawa, K.; Ochi, R.; *Koike, T.; *Akita, M.
    Organic Chemistry Frontiers, 2018, 5, 1406-1410
  • "Metal-free Di- and Tri-fluoromethylation of Alkenes Realized by Visible-light-induced Perylene Photoredox Catalysis"
    Noto, N.; *Koike, T.; *Akita, M.
    Chemical Science, 2017, 8, 6375-6379
  • "Photoredox-catalyzed Oxytrifluoromethylation of Allenes: Stereoselective Synthesis of 2-Trifluoromethylated Allyl Acetates"
    Tomita, R.; *Koike, T.;* Akita, M.
    Chemical Communications, 2017, 53, 4681-4684
  • "Photocatalytic Trifluoromethylthiolation of Aromatic Alkenes Associated with Hydroxylation and Alkoxylation"
    Li, Y.; *Koike, T.; *Akita, M.
    Asian Journal of Organic Chemistry, 2017, 6, 445-448
  • "Diastereoselective Synthesis of CF3- and CF2H‐Substituted Spiroethers from Aryl-Fused Cycloalkenylalkanols by Photoredox Catalysis"
    Noto, N.; *Koike, T.; *Akita, M.
    The Journal of Organic Chemistry, 2016, 81, 7064-7071

Review

  • 「Frontiers in Radical Fluoromethylation by Visible-Light Organic Photocatalysis 」 *Koike, T., Asian Journal of Organic Chemistry, 9, 529-537, 2020
  • 「Recent Progress in Photochemical Radical Di- and Mono-Fluoromethylation」 *Koike, T.; *Akita, M., Organic & Biomolecular Chemistry, 17, 5413-5419, 2019
  • 「New Horizons of Photocatalytic Fluoromethylative Difunctionalization of Alkenes」 *Koike, T.; *Akita, M., Chem, 4, 409-437, 2018
  • 「Combination of Organotrifluoroborates with Photoredox Catalysis Marking a New Phase in Organic Radical Chemistry」 *Koike, T.; *Akita, M., Organic & Biomolecular Chemistry, 14, 6886-6890, 2016
  • 「Fine Design of Photoredox Systems for Catalytic Fluoromethylation of Carbon−Carbon Multiple Bonds」 *Koike, T.; *Akita, M., Accounts of Chemical Research, 49, 1937-1945, 2016

Conference

  • 4th International Symposium on Precisely Designed Catalysts with Customized Scaffolding
    "New Design of Highly Reducing Organic Photoredox Catalysts", Invited Lecture
    Koike, T.
    12/3/2019~12/5/2019, Nara, Japan
  • Gordon Research Conference: Light-Driven Reactions, Materials and Devices
    "Design of Photoredox Systems for Metal-Free Radical Fluoroalkylation", Invited Lecture
    Koike, T.
    7/14/2019~7/19/2019, Boston, USA
  • 9th Pacific Symposium on Radical Chemistry
    "Photoredox-Catalyzed Reactions of N-Aminopyridinium Derivatives", Invited Lecture
    Koike, T.; Matsushita, Y.; Miyazawa, K.; Ochi, R.; Akita, M.
    6/16/2019~6/21/2019, Pacific Grove, USA
  • The 1st Sino-Japanese Symposium on Catalysis for Precision Synthesis 
    "Design of Photoredox Systems for Catalytic Fluoromethylation of Alkenes", Invited Lecture
    Koike, T.
    5/27/2018~5/30/2018, Shanghai, China
  • The 233rd ECS Meeting
    "Design of Photoredox Systems for Catalytic Fluoroalkylation of Alkenes", Invited Lecture
    Koike, T.
    5/13/2018~5/17/2018, Seattle, USA
  • International CLS Forum on "Photo and Catalytic Science for Sustainable Society"
    "Design of Photoredox Systems for Fluoromethylation of Alkenes", Oral Presentation
    Koike, T.; Akita, M.
    3/3/2018~3/4/2018, Tokyo, Japan
  • The 11th International Conference on Cutting-Edge Organic Chemistry in Asia
    "Stereoselective Synthesis of Tetrasubstituted CF3-Alkenes via Photoredox-Catalyzed Sulfonyloxytrifluoromethylation of Internal Alkynes", Poster Presentation
    Tomita, R.; Koike, T.; Akita, M.
    10/27/2016~10/30/2016, Daejeon, Korea
  • 2016 Pacific Rim Meeting on Electrochemical and Solid-State Science (PRiME 2016)
    "Photoredox Catalysis: An Easy Access to Versatile Radical Functionalization", Invited Lecture
    Koike, T.
    10/2/2016~10/7/2016, Honolulu, USA
  • 1st International Symposium on Precisely Designed Catalysts with Customized Scaffolding 
    "Fluoromethylative Difunctionalization of Olefins by Photoredox Catalysis", Invited Lecture
    Koike, T.; Yasu, Y.; Tomita, R.; Akita, M.
    7/9/2016~7/9/2016, Osaka, Japan

National Conference

  • 日本化学会 第97春季年会
    "Fine Design of Photoredox Systems for Catalytic Fluoromethylation", 招待講演
    Koike, T.
    3/16/2017~3/19/2017, 横浜
  • 日本化学会 青森地区講演会
    "フォトレドックス触媒反応:電子と光を試薬とする触媒反応", 招待講演
    Koike, T.
    10/14/2016~10/14/2016, 弘前

Media

  • Organic Chemistry Frontiers, カバーピクチャ
    Miyazawa, K.; Ochi, R.; Koike, T.; Akita, M., 5/7/2018
    PDF File
  • Chemical Communications, カバーピクチャ
    Tomita, R.; Koike, T.; Akita, M., 4/25/2017
    PDF File
  • Asian Journal of Organic Chemistry, カバーピクチャ
    Li Y.; Koike, T.; Akita, M., 4/14/2017
    PDF File
  • Organic & Biomolecular Chemistry, カバーピクチャ
    Koike, T.; Akita, M., 7/21/2016
    PDF File