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2016 Fiscal Year Annual Research Report

sp3 炭素アニオン活性種制御を基軸とする機能性物質創製法の開発

Research Project

Project/Area Number 26288049
Research InstitutionKyoto University

Principal Investigator

永木 愛一郎  京都大学, 工学(系)研究科(研究院), 講師 (80452275)

Project Period (FY) 2014-04-01 – 2018-03-31
Keywordsフローマイクロリアクター / アルキルリチウム / 保護基フリー合成
Outline of Annual Research Achievements

高活性な有機金属中間体と複数の官能基を有する求電子剤との反応は、速い競争的逐次反応に分類できる。申請者らは、速い競争的逐次反応の選択性の制御に対し、マイクロリアクターの高速混合の利用が極めて有効であることを報告している。そこで、高活性な有機金属種と多官能性求電子剤との高速混合をマイクロミキサーにより実現することで、官能基選択的求核反応の検討を行った。フローマイクロリアクターを用いた求電子性官能基を有するアリールリチウム種と二官能性求電子剤との反応で、バッチ反応にくらべて高い官能基選択性が発現した。マイクロミキサーによる高速混合により、高い選択性が得られたものと推定される。

Current Status of Research Progress
Current Status of Research Progress

2: Research has progressed on the whole more than it was originally planned.

Reason

計画通り研究が進んでいるため。

Strategy for Future Research Activity

グリコシルアニオン中間体の発生と反応の研究開発をスタートする。

  • Research Products

    (16 results)

All 2017 2016

All Journal Article (9 results) (of which Peer Reviewed: 8 results) Presentation (5 results) (of which Int'l Joint Research: 5 results,  Invited: 5 results) Book (2 results)

  • [Journal Article] Flow microreactor synthesis of 2,2-disubstituted oxetanes via 2-phenyloxetan-2-yl lithium2016

    • Author(s)
      Degennaro, L.; Nagaki, A.; Moriwaki, Y.; Romanazzi, G.; Dell’Anna, M. M.; Yoshida, J.; Luisi, R
    • Journal Title

      Flow microreactor synthesis of 2,2-disubs Open Chem.

      Volume: 14 Pages: 377-382

    • DOI

      10.1515/chem-2016-0041

    • Peer Reviewed
  • [Journal Article] マイクロ流路を利用した空間的反応集積化2016

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

      化学と工業

      Volume: 69 Pages: 117-119

    • Peer Reviewed
  • [Journal Article] Flash Cationic Polymerization Followed by Bis-end-functionalization. A New Approach to Linear-Dendritic Hybrid Polymers2016

    • Author(s)
      Tani, Y.; Takumi, M.; Moronaga, S.; Nagaki, A.*; Yoshida, J.*
    • Journal Title

      Eur. Poly. J.

      Volume: 80 Pages: 227-233

    • DOI

      10.1016/j.eurpolymj.2016.02.021

    • Peer Reviewed
  • [Journal Article] Design of a Numbering-up System of Monolithic Microreactors and Its Application to Synthesis of a Key Intermediate of Valsaltan2016

    • Author(s)
      Nagaki, A.*; Hirose, K.; Tonomura, O.; Taga, T.; Taniguchi, S.; Hasebe, S.; Ishizuka, N.; Yoshida, J.*
    • Journal Title

      Org. Process Res. Dev.

      Volume: 20 Pages: 687-691

    • DOI

      10.1021/acs.oprd.5b00414

    • Peer Reviewed
  • [Journal Article] Generation and Reaction of Carbamoyl Anions in Flow: Applications in the Three-Component Synthesis of Functionalized α-Ketoamides2016

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

      Angew. Chem., Int. Ed.

      Volume: 55 Pages: 5327-5331

    • DOI

      10.1002/anie.201601386

    • Peer Reviewed
  • [Journal Article] Integration of borylation of aryllithiums and Suzuki-Miyaura coupling using monolithic Pd catalyst2016

    • Author(s)
      Nagaki, A.*; Hirose, K.; Moriwaki, Y.; Mitamura, K.; Matsukawa, K.; Ishizuka, N.; Yoshida, J.*
    • Journal Title

      Catal. Sci. Tech.

      Volume: 6 Pages: 4690-4694

    • DOI

      10.1039/C5CY02098K

    • Peer Reviewed
  • [Journal Article] Feasibility Study on Continuous Flow Controlled/Living Anionic Polymerization Processes2016

    • Author(s)
      Nagaki, A.*; Nakahara, Y.; Furusawa, M.; Sawaki, T.; Yamamoto, T.; Toukairin, H.; Tadokoro, S.; Shimazaki, T.; Ito, T.; Otake, M.; Arai, H.; Higashida, N.; Takahashi, Y.; Moriwaki, Y.; Tsuchihashi, Y.; Hirose, K.; Yoshida, J.*
    • Journal Title

      Org. Process Res. Dev.

      Volume: 20 Pages: 1377-1382

    • DOI

      10.1021/acs.oprd.6b00158

    • Peer Reviewed
  • [Journal Article] Switching Between Intermolecular and Intramolecular Reactions Using Flow Microreactors. Lithiation of 2-Bromo-2'-Silylbiphenyls2016

    • Author(s)
      Nagaki, A.*; Kim, S.; Miuchi, N.; Yamashita, H.; Hirose, K.; Yoshida, J.*
    • Journal Title

      Org. Chem. Front.

      Volume: 3 Pages: 1250-1253

    • DOI

      10.1039/C6QO00257A

    • Peer Reviewed
  • [Journal Article] Flow Microreactor Polymerization2016

    • Author(s)
      Nagaki, A.*
    • Journal Title

      Chemical Engineering

      Pages: in press

  • [Presentation] Organolithium Chemistry Using Flow Microreactors and Its Applications to Palladium Catalyzed Crosscoupling2017

    • Author(s)
      aiichiro nagaki
    • Organizer
      International Conference on Catalysis and Chemical Engineering
    • Place of Presentation
      Baltimore, USA
    • Year and Date
      2017-02-22 – 2017-02-24
    • Int'l Joint Research / Invited
  • [Presentation] Anionic Polymerizations Using Flow Microreactors2016

    • Author(s)
      aiichiro nagaki
    • Organizer
      Polymer Chemistry 2016 International Conference,
    • Place of Presentation
      Atlanta, USA
    • Year and Date
      2016-11-14 – 2016-11-16
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis of Organofluorine Compounds Using Flow Microreactors2016

    • Author(s)
      aiichiro nagaki
    • Organizer
      2nd World Chemistry Conference,
    • Place of Presentation
      Toronto, Canada
    • Year and Date
      2016-08-08 – 2016-08-10
    • Int'l Joint Research / Invited
  • [Presentation] Organolithium Chemistry Using Flow Microreactors to Green Chemistry2016

    • Author(s)
      aiichiro nagaki
    • Organizer
      7th Annual Global Congress of Catalysis 2016,
    • Place of Presentation
      Seoul, South Korea
    • Year and Date
      2016-06-30 – 2016-07-03
    • Int'l Joint Research / Invited
  • [Presentation] Remarkable Chemoselectivity by Flash Chemistry2016

    • Author(s)
      aiichiro nagaki
    • Organizer
      The 12th International Symposium on Organic Reactions
    • Place of Presentation
      Kyoto, Japan
    • Year and Date
      2016-04-22 – 2016-04-24
    • Int'l Joint Research / Invited
  • [Book] フローマイクロ合成の実用化への展望2016

    • Author(s)
      Kim, H.; Nagaki, A.; Yoshida, J.
    • Total Pages
      211
    • Publisher
      シーエムシー出版
  • [Book] Organometallic Flow Chemistry2016

    • Author(s)
      Nagaki, A.; Yoshida, J.
    • Total Pages
      38
    • Publisher
      Springer Nature

URL: 

Published: 2018-01-16  

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