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2013 Fiscal Year Final Research Report

Organic Synthesis

Planned Research

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Project AreaOrganic Synthesis based on Integration of Chemical Reactions. New Methodologies and New Materials
Project/Area Number 21106002
Research Category

Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionKyoto University

Principal Investigator

YOSHIDA Jun-ichi  京都大学, 工学(系)研究科(研究院), 教授 (30127170)

Co-Investigator(Kenkyū-buntansha) NOKAMI Toshiki  京都大学, 大学院工学研究科, 講師 (60402963)
SHIMIZU Akihiro  京都大学, 大学院工学研究科, 助教 (30584263)
Project Period (FY) 2009-07-23 – 2014-03-31
Keywords有機合成 / 炭素カチオン / 炭素アニオン / 有機電解 / フロー合成
Research Abstract

We developed the time integration of electrochemical and chemical reactions using the cation pool method, and applied it to the synthesis of functional materials such as dendritic molecules. The space integration of cationic reactions using flow microreactors was also achieved, and new transformations such as cationic three-component coupling reactions were developed. The space integration of anionic species was also achieved. We showed that a flow microreactor enables the generation and reactions of highly unstable organolithium species such as aryllithium species bearing ketone carbonyl groups. The method was successfully applied to the formal synthesis of a natural product. We also showed that flow microreactors allow generation and use of configurationally unstable chiral organolithium species.
In summary, we developed various transformations that are difficult to achieve by conventional methods based on reaction integration via short-lived, highly reactive ionic species.

  • Research Products

    (29 results)

All 2014 2013 2012 2011 2010 Other

All Journal Article (11 results) (of which Peer Reviewed: 11 results) Presentation (16 results) (of which Invited: 9 results) Book (1 results) Remarks (1 results)

  • [Journal Article] Halogen and Chalcogen Cation Pools Stabilized by DMSO. Versatile Reagents for Alkene Difunctionalization2013

    • Author(s)
      Ashikari, Y.; Shimizu, A.; Nokami, T.; Yoshida, J
    • Journal Title

      J. Am. Chem. Soc

      Volume: 135 Pages: 16070-16073

    • DOI

      10.1021/ja4092648

    • Peer Reviewed
  • [Journal Article] Automated Solution-Phase Synthesis of Oligosaccharides via Iterative electrochemical Assembly of Thioglycosides2013

    • Author(s)
      Nokami, T.; Hayashi, R.; Saigusa, Y.; Shimizu, A.; Liu, C.-Y.; Mong, K.-K. T.; Yoshida, J
    • Journal Title

      Org. Lett

      Volume: 15 Pages: 4520-4523

    • DOI

      10.1021/ol402034g

    • Peer Reviewed
  • [Journal Article] Electrochemical C-H Amination: Synthesis of Aromatic Primary Amines via N-Arylpyridinium Ions2013

    • Author(s)
      Morofuji, T.; Shimizu, A.; Yoshida, J
    • Journal Title

      J. Am. Chem. Soc

      Volume: 135 Pages: 5000-5003

    • DOI

      10.1021/ja402083e

    • Peer Reviewed
  • [Journal Article] Asymmetric Carbolithiation of Conjugated Enynes: A Flow Microreactor Enables the Use of Configurationally Unstable Intermediates before They Epimerize2013

    • Author(s)
      Tomida, Y.; Nagaki, A.; Yoshida, J
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Pages: 3744-3747

    • DOI

      10.1021/ja110898s

    • Peer Reviewed
  • [Journal Article] Flow synthesis of arylboronic esters bearing electrophilic functional groups and space integration with Suzuki-Miyaura coupling without intentionally added base2012

    • Author(s)
      Nagaki, A.; Moriwaki, Y.; Yoshida, J
    • Journal Title

      Chem. Commun

      Volume: 48 Pages: 11211-11213

    • DOI

      10.1039/C2CC36197C

    • Peer Reviewed
  • [Journal Article] Morofuji, T.; Shimizu, A.; Yoshida, J2012

    • Author(s)
      Metal- and Chemica-Oxidant-Free C-H/C-H Cross- Coupling of Aromatic Compounds Using "Radical Cation Pools"
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 51 Pages: 7259-7262

    • DOI

      10.1002/anie.201202788

    • Peer Reviewed
  • [Journal Article] Lithiation of 1,2-Dichloroethene in Flow Microreactors. Versatile Synthesis of Alkenes and Alkynes by Precise Residence-Time Control2012

    • Author(s)
      Nagaki, A.; Matsuo, C.; Kim, S.; Saito, K.; Miyazaki, A.; Yoshida, J
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 51 Pages: 3245-3248

    • DOI

      10.1002/anie.201108932

    • Peer Reviewed
  • [Journal Article] A flow microreactor approach to protecting-group-free synthesis using organolithium compounds2011

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

      Nat. Commun

      Volume: 2 Pages: 264

    • DOI

      10.1038/ncomms1264

    • Peer Reviewed
  • [Journal Article] Indirect Cation Flow Method. Flash Generation of Alkoxycarbenium Ions and Studies on Stability of Glycosyl Cations2011

    • Author(s)
      Saito, K.; Ueoka, K.; Matsumoto, K.; Suga, S.; Nokami, T.; Yoshida, J
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 50 Pages: 153-5156

    • DOI

      10.1002/anie.201100854

    • Peer Reviewed
  • [Journal Article] Integrated Electrochemical Chemical Oxidation Mediated by Alkoxysulfonium Ions2011

    • Author(s)
      Ashikari, Y.; Nokami, T.; Yoshida, J
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Pages: 11840-11843

    • DOI

      10.1021/ja202880n

    • Peer Reviewed
  • [Journal Article] Cationic Three-component Coupling Involving an Optically Active Enamine Derivative. From Time Integration to Space Integration of Reactions2010

    • Author(s)
      Suga, S.; Yamada, D.; Yoshida, J
    • Journal Title

      Chem. Lett

      Volume: 39 Pages: 404-406

    • DOI

      10.1246/cl.2010.404

    • Peer Reviewed
  • [Presentation] Strategies and Tactics in Electroorganic Synthesis: Electroauxiliary, Cation Pool, and Flow Microreactor2014

    • Author(s)
      J. Yoshida
    • Organizer
      225th Electrochemical Society Meeting
    • Place of Presentation
      Orlando, FL, USA
    • Year and Date
      20140511-15
  • [Presentation] Reaction Integration Using Cationic Reactive Intermediates2013

    • Author(s)
      J. Yoshida
    • Organizer
      The 11th International Symposium on Organic Reaction (ISOR 11)
    • Place of Presentation
      Taipei, Taiwan, ROC
    • Year and Date
      20131119-22
    • Invited
  • [Presentation] Organolithium Chemistry in Flow Microreactors Based on High-Resolution Control of Reaction Time by Space2013

    • Author(s)
      J. Yoshida
    • Organizer
      10th International Symposium on Carbanion Chemistry
    • Place of Presentation
      Kyoto Japan
    • Year and Date
      20130923-26
    • Invited
  • [Presentation] Flash Chemistry Using Flow Microreactors. Organic Synthesis That Cannot Be Done in Batch2013

    • Author(s)
      J. Yoshida
    • Organizer
      Microwave and Flow Chemistry Conference 2013
    • Place of Presentation
      Napa Valley, California, USA
    • Year and Date
      20130720-23
  • [Presentation] Flash Chemistry Using Flow Microreactors. The Principle and Applications2013

    • Author(s)
      J. Yoshida
    • Organizer
      Eight International Congress for Innovation in Chemistry (PERCH-CIC Congress VIII)
    • Place of Presentation
      Pattaya, Thailand
    • Year and Date
      20130505-08
  • [Presentation] Flash Chemistry: organic chemistry that cannot be done in batch2013

    • Author(s)
      J. Yoshida
    • Organizer
      Bürgenstock Conference 2013
    • Place of Presentation
      Brunnen, Switzerland
    • Year and Date
      20130428-0503
    • Invited
  • [Presentation] Flash Chemistry Using Flow Microreactors. The Principle and Applications2013

    • Author(s)
      J. Yoshida
    • Organizer
      The Ta-shue Chou Lectureship Award Symposium. Outstanding Achievements in Organic Synthesis
    • Place of Presentation
      Academia Sinica, Taipei, Taiwan
    • Year and Date
      2013-03-08
  • [Presentation] Hot Reagents in High-tech Reactors2012

    • Author(s)
      J. Yoshida
    • Organizer
      GRIGNARD: 100 ans de modernite d'un Prix Nobel (100 year anniversary of Nobel Prize)
    • Place of Presentation
      Lyon, France
    • Year and Date
      20120621-22
    • Invited
  • [Presentation] Flash Chemistry Using Flow Microreactors. Principle and Applications2012

    • Author(s)
      J. Yoshida
    • Organizer
      5th Siegfried Symposium
    • Place of Presentation
      Zurich, Switzerland
    • Year and Date
      2012-10-05
    • Invited
  • [Presentation] Organic Electrochemistry, Microreactors, and Their Synergy2011

    • Author(s)
      J. Yoshida
    • Organizer
      10th International Symposium Organic Reactions (ISOR-10)
    • Place of Presentation
      Yokohama, Japan
    • Year and Date
      20111121-24
  • [Presentation] Flash Chemistry: Fast Chemical Synthesis Using Flow Microreactors2011

    • Author(s)
      J. Yoshida
    • Organizer
      2ndAsia-Pacific Chemical and Biological Microfluidics Conference
    • Place of Presentation
      Nanjing, China
    • Year and Date
      20110525-27
  • [Presentation] Flash Chemistry Fast Chemical Synthesis in Flow Microreactors2010

    • Author(s)
      J. Yoshida
    • Organizer
      The 14th International Conference on Miniaturized Systems for Chemistry and Life Sciences
    • Place of Presentation
      Groningen, The Netherlands
    • Year and Date
      20101003-07
  • [Presentation] Flash Chemistry Fast Chemical Synthesis in Flow Microreactors2010

    • Author(s)
      J. Yoshida
    • Organizer
      Ischia Advanced School of Organic Chemistry
    • Place of Presentation
      Ischia Porto, Napoli, Italy
    • Year and Date
      20100925-29
    • Invited
  • [Presentation] Synergy between Organic Electrochemistry and Flow Microreactor Chemistry2010

    • Author(s)
      J. Yoshida
    • Organizer
      PacifiChem 2010, Green Electrochemistry
    • Place of Presentation
      Hawaii, U.S.A.
    • Year and Date
      2010-12-17
    • Invited
  • [Presentation] Flash chemistry using flow microreactors2010

    • Author(s)
      J. Yoshida
    • Organizer
      PacifiChem2010. Achieving Efficiency in Organic Reactions via Greener Processes and Practices
    • Place of Presentation
      Hawaii, U.S.A.
    • Year and Date
      2010-12-17
    • Invited
  • [Presentation] Iterative Molecular Assembly Based on the Cation-Pool Method. Convergent Synthesis of Dendritic Molecules2010

    • Author(s)
      J. Yoshida
    • Organizer
      First German-Japanese Symposium on Electrosynthesis
    • Place of Presentation
      Bonn, Germany
    • Year and Date
      2010-10-02
    • Invited
  • [Book] Synthesis Assisted by Electricity, in Handbook of Green Chemistry - Green Processes. Vol. 72012

    • Author(s)
      Yoshida, J.; Suga, S
    • Publisher
      Green Synthesis, Li, C.-J. Ed. Wiley-VCH
  • [Remarks]

    • URL

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

URL: 

Published: 2015-06-25  

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