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A Flow Microreactor Approach to Protecting-group Free Synthesis

Research Project

Project/Area Number 22750092
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionKyoto University

Principal Investigator

NAGAKI Aiichiro  京都大学, 大学院・工学研究科, 助教 (80452275)

Project Period (FY) 2010 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2011: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Fiscal Year 2010: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywordsマイクロ合成 / 保護基フリー合成 / 有機金属合成 / 活性種合成 / 迅速合成 / 活性種化学
Research Abstract

We have developed a flow-microreactor approach to protecting-group free synthesis. In this research, we have found that the use of flow microreactor systems could be effective method for(2)generation and reactions of aryllithiums bearing electrophilic functional groups such as alkoxycarbonyl, cyano and nitro groups that such transformations are very difficult or impossible with a conventional macrobatch system(2)generation and reactions of aryllithiums bearing ketone carbonyl groups that such transformations are impossible with a conventional macrobatch system, and(3)the formal synthesis of Malachite green.

Report

(3 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • Research Products

    (49 results)

All 2012 2011 2010

All Journal Article (39 results) (of which Peer Reviewed: 39 results) Presentation (10 results)

  • [Journal Article] Non-additive Substituent Effects on Expanding Prestrained C-C Bond in Crystal : X-ray Analyses on Unsymmetrically Substituted Tetraarylpyracenes Prepared by a Flow Microreactor Method2012

    • Author(s)
      Suzuki, T.; Uchimura, Y.; Ishigaki, Y.; Takeda, T.; Katoono, R.; Kawai, H.; Fujiwara, K.; Nagaki, A.; Yoshida, J.
    • Journal Title

      Chem.Lett

      Volume: 1(in press)

    • NAID

      10030619852

    • Related Report
      2011 Annual Research Report
    • 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 Issue: 13 Pages: 3245-3248

    • DOI

      10.1002/anie.201108932

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cross-coupling of Aryllithiums with Aryl and Vinyl Halides in Flow Microreactors2012

    • Author(s)
      永木愛一郎, 森脇佑也, 原木優, 見目章, 林篤志, 吉田潤一
    • Journal Title

      Chem. -Asian J.

      Volume: 7 Issue: 5 Pages: 1061-1068

    • DOI

      10.1002/asia.201101019

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] マイクロリアクターを使った環境調和型有機合成、高分子合成技術2012

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

      「マイクロリアクター技術の最前線」シーエムシー出版

      Volume: 1 Pages: 72-79

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Flow Microreactor Synthesis of Tricyclic Sulfonamides via N-Ts-Aziridinyllithiums2012

    • Author(s)
      Takizawa, E.; Nagaki, A.; Yoshida, J.
    • Journal Title

      Tetrahedron Lett

      Volume: 53 Pages: 1397-1400

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Flow Microreactor Systems for Organic Synthesis : A New Synthetic Chemistry from Space Controlling Time2012

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

      Chemical Education

      Volume: (n press)

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Practical Synthesis of Photochromic Diarylethenes in Integrated Flow Microreactor Systems.2012

    • Author(s)
      Asai, T.; Takata, A.; Nagaki, A.; Yoshida, J
    • Journal Title

      ChemSusChem

      Volume: 5 Issue: 2 Pages: 339-350

    • DOI

      10.1002/cssc.201100376

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Green and Sustainable Chemical Synthesis Using Flow Microreactors2011

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

      ChemSusChem

      Volume: 4 Pages: 331-340

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Carbolithiation of Conjugated Enynes: A Flow Microreactor Enables the Use of Configurationally Unstable Intermediates before They Epimerize2011

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

      J. Am. Chem. Soc.

      Volume: 133 Issue: 31 Pages: 3744-3747

    • DOI

      10.1002/chin.201131063

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • 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 Issue: 1 Pages: 264-264

    • DOI

      10.1038/ncomms1264

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Hysteretic Tricolor Electrochromic Systems Based on the Dynamic Redox Properties of Unsymmetrically Substituted Dihydrophenanthrenes and Biphenyl-2,2'-Diyl Dications : Efficient Precursor Synthesis by a Flow Microreactor Method2011

    • Author(s)
      Yusuke Ishigaki, et al
    • Journal Title

      Materials

      Volume: 4 Issue: 11 Pages: 1906-1926

    • DOI

      10.3390/ma4111906

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Flash Synthesis of TAC-101 and Its Analogues from 1,3,5-Tribromobenzene Using Integrated Flow Microreactor Systems2011

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

      RSC Advances

      Volume: 1 Issue: 5 Pages: 758-760

    • DOI

      10.1039/c1ra00377a

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Perfluoroalkylation in Flow Microreactor: Generation of Perfluoroalkyllithiums in the Presence and Absence of Electrophiles2011

    • Author(s)
      Nagaki, A.; Tokuoka, S.; Yamada, S.; Tomida, Y.; Oshiro, K.; Amii, H.; Yoshida, J.
    • Journal Title

      Org. Biomol. Chem.

      Volume: 9 Issue: 21 Pages: 7559-7563

    • DOI

      10.1039/c1ob06350b

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Homocoupling of aryl halides in flow: Space integration of lithiation and FeCl3 promoted homocoupling2011

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

      Org. Chem.

      Volume: 7 Pages: 1064-1039

    • DOI

      10.3762/bjoc.7.122

    • NAID

      120004996582

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Space Integration of Reactions: An Approach to Increase the Capability of Organic Synthesis2011

    • Author(s)
      Yoshida, J.; Saito, K.; Nokami, T.; Nagaki,A.
    • Journal Title

      Synlett

      Volume: 9 Issue: 09 Pages: 1189-1194

    • DOI

      10.1055/s-0030-1259946

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Addition Polymerization using Flow Microreactor Systems and its Applicationsto Syntheses of Structurally Well-definedPolymer2011

    • Author(s)
      Nagaki, A
    • Journal Title

      Kobunshi Ronbunshu

      Volume: 68 Pages: 521-531

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] New Development of Organic Lithium Chemistry by Microreactor2011

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

      Kemikaru Enjiniyaringu

      Volume: 56 Pages: 54-63

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Switching Reaction Pathways of Benzo[b]thiophen-3-yllithium and Benzo[b]furan-3-yllithium Based on High-Resolution Residence-Time and Temperature Control in a Flow Microreactor2011

    • Author(s)
      Asai, A.; Takata, A.; Ushiogi, Y.; Iinuma, Y.; Nagaki, A.; Yoshida, J.
    • Journal Title

      Chem. Lett.

      Volume: 40 Issue: 4 Pages: 393-395

    • DOI

      10.1246/cl.2011.393

    • NAID

      10028170699

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Flow Microreactor Synthesis of Disubstituted Pyridines from Dibromopyridines via Br/Li Exchange without Using Cryogenic Conditions2011

    • Author(s)
      Nagaki, A.; Yamada, S.; Doi, M.; Tomida, Y.; Takabayashi, N.; Yoshida, J.
    • Journal Title

      Green Chem.

      Volume: 13 Issue: 5 Pages: 1110-1113

    • DOI

      10.1039/c0gc00852d

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Anionic Polymerization of Alkyl Methacrylates using Flow Microreactor Systems2011

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

      Chem. Eng. J

      Volume: 167 Pages: 548-555

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Generation and Reactions of Oxiranyllithiums Using a Flow Microreactor2011

    • Author(s)
      Nagaki, A.; Takizawa. E.; Yoshida, J.
    • Journal Title

      Chem.Eur.J.

      Volume: 16 Issue: 47 Pages: 14149-14158

    • DOI

      10.1002/chem.201000815

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Anionic Polymerization of Alkyl Methacrylates using Flow Microreactor Systems2011

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

      Chem. Eng. J.

      Volume: 167 Issue: 20 Pages: 548-555

    • DOI

      10.1021/ma101663x

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Addition Polymerization using Flow Microreactor Systems and its Applications to Syntheses of Structurally Well-defined Polymer2011

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

      Kobunshi Ronbunshu

      Volume: 66 Pages: 521-531

    • NAID

      10029472731

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Anionic Polymerization of Alkyl Methacrylates using Flow Microreactor Systems2011

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

      Chem.Eng.J

      Volume: 167 Pages: 548-555

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Green and Sustainable Chemical Synthesis Using Flow Microreactors2011

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

      ChemSusChem

      Volume: 4 Issue: 3 Pages: 331-340

    • DOI

      10.1002/cssc.201000271

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Carbolithiation of Conjugated Enynes : A Flow Microreactor Enables the Use of Configurationally Unstable Intermediates before They Epimerize A2011

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

      J.Am.Chem.Soc.

      Volume: 133 Pages: 3744-3747

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Green and Sustainable Chemical Synthesis Using Flow Microreactors2011

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

      Chem.Sus.Chem.

      Volume: 4 Pages: 331-340

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Anionic Polymerization of Alkyl Methacrylates using Flow Microreactor Systems2011

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

      Chem.Eng.J.

      Volume: 167 Pages: 548-555

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cross-Coupling in a Flow Microreactor. Space Integration of Lithiation and Murahashi Coupling2010

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

      Angew.Chem.Int.Ed

      Volume: 49 Issue: 41 Pages: 7543-7547

    • DOI

      10.1002/anie.201002763

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] A Flow Microreactor System Enables Organolithium Reactions without Protecting Alkoxycarbonyl Groups2010

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

      Chem.Eur.J

      Volume: 16 Issue: 36 Pages: 11167-11177

    • DOI

      10.1002/chem.201000876

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Controlled Polymerizations Using Microreactors2010

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

      Kobunsh

      Volume: 59 Pages: 569-573

    • NAID

      10026493625

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Generation and Reaction of Cyano-substituted Aryllithium Compounds using Microreactors2010

    • Author(s)
      Nagaki, A.; Kim, H.; Matsuo, C.
    • Journal Title

      Org.Biomol.Chem.

      Volume: 8 Issue: 5 Pages: 1212-1217

    • DOI

      10.1039/b919325c

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Building Addressable Libraries as Platforms for Biological Assays by an Electrochemical2010

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

      iAngew.Chem., Int.Ed.

      Volume: 49 Issue: 22 Pages: 3720-3722

    • DOI

      10.1002/anie.201000046

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Generation and Reactions of Oxiranyllithiums Using a Flow Microreactor2010

    • Author(s)
      Nagaki, A.; Takizawa, E.; Yoshida, J.
    • Journal Title

      Chem.-Eur.J.

      Volume: 16 Pages: 14149-14158

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Polystyrenes-Poly(alkyl methacrylates) Block Copolymers via Anionic Polymerization Using an Integrated Flow Microreactor System2010

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

      Macromolecules

      Volume: 43 Pages: 8424-8429

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cross-Coupling in a Flow Microreactor Space Integration of Lithiation and Murahashi Coupling2010

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

      Angew.Chem., Int.Ed

      Volume: 49 Pages: 7543-7547

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Flow Microreactor System Enables Organolithium Reactions without Protecting Alkoxycarbonyl Groups2010

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

      Chem.-Eur.J.

      Volume: 16 Pages: 11167-11177

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Controlled Polymerizations Using Microreactors2010

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

      Kobunshi

      Volume: 59 Pages: 569-573

    • NAID

      10026493625

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Building Addressable Libraries as Platforms for Biological Assays by an Electrochemical Method2010

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

      Angew.Chem., Int.Ed.

      Volume: 49 Pages: 3720-3722

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] 有機リチウム反応の高度制御に基づくフローマイクロ合成2012

    • Author(s)
      永木愛一郎
    • Organizer
      フロー・マイクロ合成研究会
    • Place of Presentation
      大阪
    • Year and Date
      2012-03-16
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] カルボニル基を有するアリールリチウム種を鍵中間体とするフローマイクロリアクターを用いた保護基フリー合成2011

    • Author(s)
      永木愛一郎
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川
    • Year and Date
      2011-03-27
    • Related Report
      2011 Final Research Report 2010 Annual Research Report
  • [Presentation] カルボニル基を有するアリールリチウム種を鍵中間体とするフローマイクロ2011

    • Author(s)
      永木愛一郎
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川県
    • Year and Date
      2011-03-27
    • Related Report
      2011 Annual Research Report
  • [Presentation] Cross-Coupling of Two Aryl Halides in Flow Microreactor Systems2010

    • Author(s)
      A. Nagaki
    • Organizer
      The 2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2010-12-17
    • Related Report
      2011 Final Research Report
  • [Presentation] Cross-Coupling of Two Aryl Halides in Flow Microreactor Systems.Space Integration of Halogen-Lithium Exchange and Murahashi Coupling2010

    • Author(s)
      A.Nagaki
    • Organizer
      The 2010 International Chemical Congress of Pacific Basin Societies (Pacifichem 2010)
    • Place of Presentation
      Honolulu, Hawai, USA
    • Year and Date
      2010-12-17
    • Related Report
      2010 Annual Research Report
  • [Presentation] マイクロリアクターによる精密反応制御に基づく新合成プロセスの開発2010

    • Author(s)
      永木愛一郎
    • Organizer
      京都大学若手の会
    • Place of Presentation
      京都
    • Year and Date
      2010-12-03
    • Related Report
      2011 Final Research Report
  • [Presentation] マイクロリアクターによる精密反応制御に基づく新合成プロセスの開発2010

    • Author(s)
      永木愛一郎
    • Organizer
      京都大学若手の会
    • Place of Presentation
      京都大学(招待講演)
    • Year and Date
      2010-12-03
    • Related Report
      2010 Annual Research Report
  • [Presentation] マイクロリアクターを用いたアニオン重合とその精密構造制御ポリマー合成への応用2010

    • Author(s)
      永木愛一郎
    • Organizer
      第59回高分子討論会
    • Place of Presentation
      北海道
    • Year and Date
      2010-09-16
    • Related Report
      2011 Final Research Report 2010 Annual Research Report
  • [Presentation] マイクロリアクターによる合成化学への新展開~究極の反応制御に基づく次世代合成・重合プロセスの開発を目指して~2010

    • Author(s)
      永木愛一郎
    • Organizer
      住友化学特別講演会
    • Place of Presentation
      千葉
    • Year and Date
      2010-08-26
    • Related Report
      2011 Final Research Report
  • [Presentation] マイクロリアクターによる合成化学への新展開~究極の反応制御に基づく次世代合成・重合プロセスの開発を目指して~2010

    • Author(s)
      永木愛一郎
    • Organizer
      住友化学特別講演会
    • Place of Presentation
      住友化学(株)石油化学品研究所、千葉(招待講演)
    • Year and Date
      2010-08-26
    • Related Report
      2010 Annual Research Report

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Published: 2010-08-23   Modified: 2016-04-21  

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