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Creation of Heterocyclic Compounds Based on Generation of Heavier Group 14 Element Cations and Activation of Small Molecules

Research Project

Project/Area Number 26410035
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionGunma University

Principal Investigator

Kawashima Takayuki  群馬大学, 大学院理工学府, 客員教授 (80011766)

Co-Investigator(Kenkyū-buntansha) 有井 秀和  宮崎大学, 教育学部, 准教授 (80384733)
海野 雅史  群馬大学, 大学院理工学府, 教授 (20251126)
箕浦 真生  立教大学, 理学部, 教授 (30274046)
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords合成化学 / 典型元素化学 / 複合材料・物性 / シロール / シリルカチオン / 連鎖反応 / ヒドロシリル化 / ゲルモール / 2-エチニルヒドロシラン誘導体 / ベンゾシロール誘導体 / ナフトシロール誘導体 / 分子内連鎖ヒドロシリル化反応 / 二重連鎖ヒドロシリル化反応 / ゲルマ-Friedel-Crafts反応 / ベンジルジイソプロピルシラン / ジイソプロピル-1-ナフチルシラン / ヒドリド引き抜き反応 / シリルカチオン錯体 / 1,2,3,4-テトラヒドロ-2-シラナフタレン / 立体特異的反応 / 分子内求電子置換反応 / 含ケイ素環状化合物 / ベンジルジメチルシラン / 1,2-ジヒドロ-2-シラナフタレン / アルケニルカルボカチオン
Outline of Final Research Achievements

Silacyclic compounds were synthesized by the generation of silyl cations from hydrosilanes bearing an aromatic ring and trityl cation, their reactions with alkynes, alkenes, and carbon dioxide, etc., and sequential reactions of formed carbocations with the aromatic ring. π-Extended siloles such as benzosiloles, naphthosiloles, and disiloles, etc. were synthesized by its application to aromatic compounds bearing 1 or 2 sets of alkynyl group and hydrosilyl group at the neighboring position. Furthermore, germa-Friedel-Crafts reaction was developed for the synthesis of dibenzogermoles.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (11 results)

All 2016 2015 2014

All Journal Article (4 results) (of which Peer Reviewed: 4 results,  Acknowledgement Compliant: 3 results,  Open Access: 1 results) Presentation (7 results) (of which Int'l Joint Research: 1 results)

  • [Journal Article] Regioselective and Stereospecific Dehydrogenative Annulation Utilizing Silylium Ion-Activated Alkenes2016

    • Author(s)
      H. Arii, Y. Yano, K. Nakabayashi, S. Yamaguchi, M. Yamamura, K. Mochida, T. Kawashima
    • Journal Title

      J. Org. Chem.

      Volume: 81 Issue: 15 Pages: 6314-6319

    • DOI

      10.1021/acs.joc.6b00793

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Intramolecular Chain Hydrosilylation of Alkynylphenylsilanes using a Silyl Cation as a Chain Carrier2016

    • Author(s)
      H. Arii, K. Nakabayashi, K. Mochida, T. Kawashima
    • Journal Title

      Molecules

      Volume: 21 Issue: 8 Pages: 991-991

    • DOI

      10.3390/molecules21080999

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] 256.The Chemistry of Heterasumanenes2016

    • Author(s)
      M. Saito, S. Furukawa, J. Kobayashi, T, Kawashima
    • Journal Title

      Chem. Rec.

      Volume: 16 Issue: 1 Pages: 64-72

    • DOI

      10.1002/tcr.201500211

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Silylium Ion-promoted Dehydrogenative Cyclization: Synthesis of Silicon-containing Compounds Derived from Alkynes2014

    • Author(s)
      H. Arii, T. Kurihara, K. Mochida, T. Kawashima
    • Journal Title

      Chem. Commun.

      Volume: 50 Issue: 50 Pages: 6649-6652

    • DOI

      10.1039/c4cc01648c

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Presentation] シリルカチオンを連鎖担体とする分子内連鎖ヒドロシリル化反応:π拡張シロール合成への応用2016

    • Author(s)
      川島隆幸・有井秀和
    • Organizer
      第43回有機典型元素化学討論会
    • Place of Presentation
      仙台、宮城
    • Year and Date
      2016-12-08
    • Related Report
      2016 Annual Research Report
  • [Presentation] シリルカチオンにより活性化されたアルケンを用いる立体特異的含ケイ素環状化合物の合成2015

    • Author(s)
      川島隆幸・有井秀和・持田邦夫・山村正樹
    • Organizer
      第42回有機典型元素化学討論会
    • Place of Presentation
      名古屋、愛知
    • Year and Date
      2015-12-03
    • Related Report
      2015 Research-status Report
  • [Presentation] Synthesis of 1,2,3,4-Terahydro-2-silanaphthalenes Utilizing Alkenes Activated by Silyl Cations2015

    • Author(s)
      T. Kawashima, H. Arii, K. Mochida, M. Yamamura
    • Organizer
      The 5th Asian Silicon Symposium, ASIS-5
    • Place of Presentation
      Jeju, Korea
    • Year and Date
      2015-10-18
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] シリルカチオンにより活性化された多重結合化合物を活用する含ケイ素環状化合物の合成2014

    • Author(s)
      川島隆幸・有井秀和・栗原崇・持田邦夫
    • Organizer
      第41回有機典型元素化学討論会
    • Place of Presentation
      宇部市文化会館文化ホール(山口県・宇部市)
    • Year and Date
      2014-11-27 – 2014-11-29
    • Related Report
      2014 Research-status Report
  • [Presentation] シリルカチオンによって促進される脱水素環化反応を利用した1,2,3,4-テトラヒドロ-2-シラナフタレン誘導体の合成2014

    • Author(s)
      有井秀和・川島隆幸・持田邦夫
    • Organizer
      第24回基礎有機化学討論会(第44回構造有機化学討論会、第63回有機反応化学討論会)
    • Place of Presentation
      東北大学川内キャンパス・萩ホール(宮城県・仙台市)
    • Year and Date
      2014-09-07 – 2014-09-10
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthesis of Sila-cyclic Compounds Utilizing Alkynes Activated by Silyl Cations2014

    • Author(s)
      T. Kawashima, H. Arii, T. Kurihara, K. Mochida
    • Organizer
      Seventeenth International Symposium on Silicon Chemistry
    • Place of Presentation
      Berlin (Germany)
    • Year and Date
      2014-08-03 – 2014-08-08
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthesis of Benzosilole Derivatives by Intramolecular Hydrosilylation Using a Silyl Cation as a Chain Carrier2014

    • Author(s)
      H. Arii, T. Kawashima, K. Mochida
    • Organizer
      XXVI International Conference on Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌(北海道・札幌市)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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