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Selective Synthetic Methodology Through the Control of Intramolecular Rearragements

Research Project

Project/Area Number 16K17898
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

Kim Heejin  京都大学, 工学研究科, 特定助教 (80754514)

Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2016: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywordsselective synthesis / intramolecular reaction / flow chemistry / microreactor / Fries rearrangement / Wittig rearrangement / 選択的合成 / 分子内転位反応 / フロー合成 / マイクロリアクター / フリース転位
Outline of Final Research Achievements

In this research, we developed the selective synthetic methods for controlling extremely fast intramolecular rearrangements using micro flow system. In detail, we used micro flow system for precise control of extremely short reaction time which is important for the chemical reaction involving the rapid intramolecular rearrangement. For example, Fries rearrangement and Wittig rearrangement were studied as the research target, and the selective synthesis of valuable compounds such as the biologically active molecules was achieved.

Report

(3 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • Research Products

    (18 results)

All 2018 2017 2016 Other

All Int'l Joint Research (3 results) Journal Article (5 results) (of which Int'l Joint Research: 5 results,  Peer Reviewed: 5 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (8 results) (of which Int'l Joint Research: 5 results,  Invited: 2 results) Book (1 results) Remarks (1 results)

  • [Int'l Joint Research] POSTECH(韓国)

    • Related Report
      2017 Annual Research Report
  • [Int'l Joint Research] POSTECH/Pukyoung National University(韓国)

    • Related Report
      2016 Research-status Report
  • [Int'l Joint Research]

    • Related Report
      2016 Research-status Report
  • [Journal Article] A Catalyst-Free Amination of Functional Organolithium Reagents by Flow Chemistry2018

    • Author(s)
      Heejin Kim, Yuya Yonekura, Jun-ichi Yoshida
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 57 Issue: 15 Pages: 4063-4066

    • DOI

      10.1002/anie.201713031

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Harnessing [1,4]-, [1,5]-, and [1,6]-Anionic Fries-type Rearrangements by Reaction Time Control in Flow.2017

    • Author(s)
      Kim, H.; Inoue, K.; Yoshida, J.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 56 Issue: 27 Pages: 78637866-78637866

    • DOI

      10.1002/anie.201704006

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] "Impossible" Chemistries Based on Flow and Micro.2017

    • Author(s)
      Yoshida, J.; Kim, H.; Nagaki, A.
    • Journal Title

      J. Flow Chem

      Volume: 7 Issue: 3-4 Pages: 60-64

    • DOI

      10.1556/1846.2017.00017

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Control of Tandem Isomerizations: Flow-Assisted Reactions of o-Lithiated Aryl Benzyl Ethers2017

    • Author(s)
      Hyune-Jea Lee, Heejin Kim, Jun-ichi Yoshida, Dong-Pyo Kim
    • Journal Title

      Chem. Commun.

      Volume: 54 Issue: 5 Pages: 547-550

    • DOI

      10.1039/c7cc08460a

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Submillisecond organic synthesis: Outpacing Fries rearrangement through microfluidic rapid mixing.2016

    • Author(s)
      Kim, H.; Min, K.-I.; Inoue, K.; Im, D. J.; Kim, D.-P.; Yoshida, J.
    • Journal Title

      Science

      Volume: 352 Issue: 6286 Pages: 691-694

    • DOI

      10.1126/science.aaf1389

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Presentation] Control of Rapid Rearrangements and Synthetic Applications Using Flow Microreactors2018

    • Author(s)
      Heejin Kim, Keita Inoue, Hyune-jea Lee, Kyoung-ik Min, Dong-Pyo Kim, Jun-ichi, Yoshida
    • Organizer
      ICAMS-1
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Heejin Kim, Hyune-jea Lee, Dong-pyo Kim, Jun-ichi Yoshida2018

    • Author(s)
      Control of Tandem Isomerizations of o-Lithiated Aryl Benzyl Ethers in Flow
    • Organizer
      日本化学会 第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] フローマイクロリアクターを用いた分子内フリース転位の制御2017

    • Author(s)
      井上 圭太、金 熙珍、吉田 潤一
    • Organizer
      日本化学会 第97春季年会 (2017)
    • Place of Presentation
      慶應義塾大学、横浜
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] フローマイクロリアクターを用いた不安定有機リチウム種の求電子的アミノ化反応2017

    • Author(s)
      米倉 裕哉、金 熙珍、吉田 潤一
    • Organizer
      日本化学会 第97春季年会 (2017)
    • Place of Presentation
      慶應義塾大学、横浜
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] Control of Fries Rearrangement within Microseconds to Milliseconds Using Microfluidic Devices2017

    • Author(s)
      Heejin Kim, Dong-Pyo Kim, Jun-ichi Yoshida
    • Organizer
      119st General Meeting of the Korean Chemical Society
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Continuous Flow Synthesis Using Unstable Organolithium Intermediates2017

    • Author(s)
      Heejin Kim, Hyune-jea Lee, Kyoungik Min, Keita Inoue, Do Jin Im, Dong-Pyo Kim, Jun-ichi, Yoshida
    • Organizer
      OMCOS_19
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Control of Fast Rearrangement Reactions Using Flow Microreactors2016

    • Author(s)
      Keita Inoue, Heejin Kim, Kyoung-Ik Min, Do Jin Im, Dong-Pyo Kim, Jun-ichi Yoshida
    • Organizer
      International Conference on Microreaction Technology 2016
    • Place of Presentation
      北京、中国
    • Year and Date
      2016-09-12
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Heejin Kim, Hyune-jea Lee, Dong-pyo Kim, Jun-ichi Yoshida2016

    • Author(s)
      A Flow-Microreactor Approach for Synthesis of [10]Cycloparaphenylene
    • Organizer
      International Conference on Microreaction Technology 2016
    • Place of Presentation
      北京、中国
    • Year and Date
      2016-09-12
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Book] フローマイクロ合成の実用化への展望2017

    • Author(s)
      共著(監修:吉田潤一)
    • Total Pages
      211
    • Publisher
      シーエムシー出版
    • Related Report
      2016 Research-status Report
  • [Remarks] 京都大学大学院工学研究科 合成・生物化学専攻 合成化学講座 有機合成化学研究室

    • URL

      http://www.sbchem.kyoto-u.ac.jp/yoshida-lab/

    • Related Report
      2017 Annual Research Report

URL: 

Published: 2016-04-21   Modified: 2022-07-19  

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