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Protective-group-free transformation of sugars enabled by hydrophilic photoredox catalysts

Research Project

Project/Area Number 21K14626
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionHokkaido University

Principal Investigator

Masuda Yusuke  北海道大学, 理学研究院, 助教 (20822307)

Project Period (FY) 2021-04-01 – 2023-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2022: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Fiscal Year 2021: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords光 / 水 / 糖 / 光酸化還元触媒 / 保護基フリー / ホスホニウム / ホスフィン / 白金 / 銅 / アリル化 / ホスホニウム塩 / 脱芳香族化
Outline of Research at the Start

本研究では、水溶性光触媒の開発を基盤とし、糖の保護基フリー変換反応を達成する。すなわち、可視光により励起される光酸化還元触媒にカルボン酸などの水溶性置換基を導入することで、新規水溶性光触媒を合成する。置換基を種々検討することで、触媒の酸化還元電位を調節することが可能である。これを利用して水中でラジカル反応を誘起し、無保護糖の直接変換を行う。水素移動触媒や還元剤を共存させることによって、幅広い変換反応の開発を試みる。また、本反応を利用した生物活性物質の合成や新規糖類縁体の創出へと展開する。

Outline of Final Research Achievements

Most organic reactions require the use of large amounts of toxic organic solvents, and reducing the use of organic solvents is an urgent issue from the viewpoint of sustainability. In addition, bio-related molecules such as sugars have low solubility in organic solvents. Thus, the development of organic reactions in water is highly desirable. In this study, water-soluble photocatalyst has been synthesized, which facilitates transformations of readily available sugar molecules without protecting groups. Furthermore, the method has been applied to synthesis of phosphonium salts.

Academic Significance and Societal Importance of the Research Achievements

本研究は、これまで有機溶媒中でしか利用することのできなかった光触媒反応を、水溶媒へと適用可能にした点で大きな意義がある。石油由来で有害な有機溶媒の使用量を低減することは、持続可能な社会の実現に直接貢献する成果である。また生体の主な構成要素である糖や脂溶性とイオン性を両立するホスホニウム塩は、その医薬品や機能性材料としての利用にも興味が持たれる分子群である。このことから、本研究成果は有機合成分野のみならず、幅広い分野への波及効果が期待できる。

Report

(3 results)
  • 2022 Annual Research Report   Final Research Report ( PDF )
  • 2021 Research-status Report
  • Research Products

    (23 results)

All 2023 2022 2021

All Journal Article (8 results) (of which Peer Reviewed: 8 results) Presentation (14 results) (of which Int'l Joint Research: 1 results,  Invited: 2 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Synthesis of Tetraarylphosphonium Salts from Triarylphosphines and Aryl Bromides Exploiting Light and Palladium2022

    • Author(s)
      Ikeshita Daichi、Shimura Hiroki、Miyakawa Sho、Masuda Yusuke、Ishida Naoki、Murakami Masahiro
    • Journal Title

      Chemistry Letters

      Volume: - Issue: 5 Pages: 522-524

    • DOI

      10.1246/cl.220067

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photoinduced Alcoholic α-C-H Bond Anti-Markovnikov Addition to Vinylphosphonium Bromides Followed by Wittig Olefination: Two-Step Protocol for α-C-H Allylic Alkylation of Alcohols2022

    • Author(s)
      Yoshida Masaki、Sawamura Masaya、Masuda Yusuke
    • Journal Title

      ChemCatChem

      Volume: 14 Issue: 18

    • DOI

      10.1002/cctc.202200744

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Defluorophosphonylation of Aryl Fluorides2022

    • Author(s)
      You Zhensheng、Masuda Yusuke、Iwai Tomohiro、Higashida Kosuke、Sawamura Masaya
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 87 Issue: 21 Pages: 14731-14737

    • DOI

      10.1021/acs.joc.2c02048

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photoinduced Copper-Catalyzed Asymmetric Acylation of Allylic Phosphates with Acylsilanes2022

    • Author(s)
      Ueda Yusuke、Masuda Yusuke、Iwai Tomohiro、Imaeda Keisuke、Takeuchi Hiroki、Ueno Kosei、Gao Min、Hasegawa Jun-ya、Sawamura Masaya
    • Journal Title

      Journal of the American Chemical Society

      Volume: 144 Issue: 5 Pages: 2218-2224

    • DOI

      10.1021/jacs.1c11526

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Photoinduced Hydrophosphination of Terminal Alkynes with Tri(<i>o</i>-tolyl)phosphine: Synthesis of Alkenylphosphonium Salts2022

    • Author(s)
      Ikeshita Daichi、Masuda Yusuke、Ishida Naoki、Murakami Masahiro
    • Journal Title

      Organic Letters

      Volume: - Issue: 13 Pages: 2504-2508

    • DOI

      10.1021/acs.orglett.2c00634

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Isomerization of Unprotected Aldoses to 2-Deoxyaldonic Acids Induced by Visible Light/Quinuclidine/Water-Soluble Iridium Complex in Water2021

    • Author(s)
      Masuda Yusuke、Tsuda Hiromu、Murakami Masahiro
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 94 Issue: 6 Pages: 1702-1704

    • DOI

      10.1246/bcsj.20210098

    • NAID

      130008066558

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Photocatalytic Cycloaddition Reaction of Triarylphosphines with Alkynes Forming Cyclic Phosphonium Salts2021

    • Author(s)
      Masuda Yusuke、Ikeshita Daichi、Murakami Masahiro
    • Journal Title

      Chemistry Letters

      Volume: 50 Issue: 9 Pages: 1691-1694

    • DOI

      10.1246/cl.210361

    • NAID

      130008088225

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Photoinduced Reaction of Triarylphosphines with Alkenes Forming Fused Tricyclic Phosphonium Salts2021

    • Author(s)
      Masuda Yusuke、Uno Masumi、Murakami Masahiro
    • Journal Title

      Organic Letters

      Volume: 23 Issue: 21 Pages: 8445-8449

    • DOI

      10.1021/acs.orglett.1c03168

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Presentation] 電荷によって制御された電子不足アルケンへの二重ラジカル付加反応2023

    • Author(s)
      増田 侑亮、吉田 真樹、澤村 正也
    • Organizer
      日本化学会第103春季年会(2023)
    • Related Report
      2022 Annual Research Report
  • [Presentation] アシルシランの光銅触媒不斉共役付加によるキラル1,4-ジカルボニル化合物の合成2023

    • Author(s)
      上田 悠介、末木 愛子、増田 侑亮、澤村 正也
    • Organizer
      日本化学会第103春季年会(2023)
    • Related Report
      2022 Annual Research Report
  • [Presentation] ビアリールホスフィンの光触媒環化反応によるジベンゾホスホールの合成2023

    • Author(s)
      河村 幸江、増田 侑亮、澤村 正也
    • Organizer
      日本化学会第103春季年会(2023)
    • Related Report
      2022 Annual Research Report
  • [Presentation] 光酸化還元触媒によるアルデヒド炭素―水素結合の臭化ビニルホスホニウムへのanti-マルコフニコフ付加反応2023

    • Author(s)
      森 晴菜、吉田 真樹、増田 侑亮、澤村 正也
    • Organizer
      日本化学会第103春季年会(2023)
    • Related Report
      2022 Annual Research Report
  • [Presentation] 光酸化還元触媒によるアルコールα位炭素ー水素結合の臭化ビニルホスホニウムへの anti-マルコフニコフ付加反応の開発2022

    • Author(s)
      吉田 真樹、増田 侑亮、澤村 正也
    • Organizer
      第20回次世代を担う有機化学シンポジウム
    • Related Report
      2022 Annual Research Report
  • [Presentation] Photocatalytic Synthesis of Organophosphorus Compounds2022

    • Author(s)
      Yusuke Masuda
    • Organizer
      The 15th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-15)
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Photoinduced Copper-Catalyzed Asymmetric Acylation of Allylic Phosphates with Acylsilanes2022

    • Author(s)
      Yusuke Ueda, Yusuke Masuda, Tomohiro Iwai, Keisuke Imaeda, Hiroki Takeuchi, Kosei Ueno, Min Gao, Jun-ya Hasegawa, Masaya Sawamura
    • Organizer
      第68回有機金属化学討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] Ni-Catalyzed Defluorophosphonylation of Aryl Fluorides2022

    • Author(s)
      Zhensheng You, Yusuke Masuda, Tomohiro Iwai, Kosuke Higashida, Masaya Sawamura
    • Organizer
      第68回有機金属化学討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] ビニルホスホニウム塩の光酸化還元反応による多様性指向型分子変換2022

    • Author(s)
      増田 侑亮、吉田 真樹、澤村 正也
    • Organizer
      第 49 回 有機典型元素化学討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] アシルシランのα,β-不飽和ケトンおよびアルデヒドへの光銅触媒不斉共役付加反応の開発2022

    • Author(s)
      末木愛子、上田悠介、増田侑亮、澤村正也
    • Organizer
      日本化学会第102春季年会(2022)
    • Related Report
      2021 Research-status Report
  • [Presentation] 光酸化還元触媒によるアルコールα位炭素―水素結合の臭化ビニルホスホニウムへのanti-マルコフニコフ付加反応2022

    • Author(s)
      吉田真樹、増田侑亮、澤村正也
    • Organizer
      日本化学会第102春季年会(2022)
    • Related Report
      2021 Research-status Report
  • [Presentation] Ni-Catalyzed Defluorophosphonylation of Aryl Fluorides2022

    • Author(s)
      Zhensheng You, Kosuke Higashida, Tomohiro Iwai, Yusuke Masuda, Masaya Sawamura
    • Organizer
      日本化学会第102春季年会(2022)
    • Related Report
      2021 Research-status Report
  • [Presentation] Photoinduced Copper-Catalyzed Asymmetric Acylation of Allylic Phosphates with Acylsilanes2022

    • Author(s)
      Yusuke Ueda, Yusuke Masuda, Tomohiro Iwai, Keisuke Imaeda, Hiroki Takeuchi, Kosei Ueno, Min Gao, Jun-ya Hasegawa, Masaya Sawamura
    • Organizer
      日本化学会第102春季年会(2022)
    • Related Report
      2021 Research-status Report
  • [Presentation] アリールホスフィンの劇的な骨格変換を伴う光カップリング反応2021

    • Author(s)
      増田侑亮
    • Organizer
      若手研究者のための有機化学札幌セミナー
    • Related Report
      2021 Research-status Report
    • Invited
  • [Patent(Industrial Property Rights)] 第4級ホスホニウム化合物の製造方法2023

    • Inventor(s)
      増田侑亮、吉田真樹、澤村正也
    • Industrial Property Rights Holder
      国立大学法人北海道大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2023
    • Related Report
      2022 Annual Research Report

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Published: 2021-04-28   Modified: 2024-01-30  

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