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Efficient synthesis of compounds having various substitution patterns using ligand-controlled site-selective reactions

Research Project

Project/Area Number 15K18833
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionUniversity of Shizuoka

Principal Investigator

Yamaguchi Miyuki  静岡県立大学, 薬学部, 助教 (70548932)

Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2016: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2015: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords触媒 / 位置選択性 / 配位子 / 有機化学 / クロスカップリング
Outline of Final Research Achievements

In this study, ligand-controlled site-selective reactions, which are powerful tools for effective synthesis of multisubstituted compounds, were developed. Dihydroxyterphenylphosphine (DHTP), which was previously developed by our group, was employed as a ligand, and various reactions were screened using a catalyst derived palladium and DHTP. As a result, arylation of nonsubstituted indole with chloroarenes proceeded C3-selectively using Pd-DHTP catalyst. On the other hand, other commercially available ligands used in cross coupling of chloroarenes afforded N-arylated product selectively. In addition, several DHTP analogs were designed as a new ligands and synthesized. These ligand showed different reactivity and site-selectivity from those of DHTP.

Report

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

    (13 results)

All 2017 2016 2015 Other

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

  • [Journal Article] Three-Step Synthesis of Fluoranthenes through Pd-Catalyzed Inter and Intramolecular C-H Arylation2016

    • Author(s)
      Miyuki Yamaguchi, Mayu Higuchi, Kanae Tazawa, Kei Manabe
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 81 Issue: 9 Pages: 3967-3974

    • DOI

      10.1021/acs.joc.6b00553

    • Related Report
      2016 Annual Research Report 2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] One-Pot Synthesis of Substituted Benzo[b]furans and Indoles from Dichlorophenols/Dichloroanilines Using a Palladium-Dihydroxyterphenylphosphine Catalyst2016

    • Author(s)
      Miyuki Yamaguchi, Tomoyo Akiyama, Hirohisa Sasou, Haruka Katsumata, Kei Manabe
    • Journal Title

      J. Org. Chem.

      Volume: 81 Issue: 13 Pages: 5450-5463

    • DOI

      10.1021/acs.joc.6b00824

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Scalable Synthesis of Dihydroxyterphenylphosphine Ligands2015

    • Author(s)
      Miyuki Yamaguchi, Kohei Suzuki, Kei Manabe
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 18 Pages: 2743-2747

    • DOI

      10.1016/j.tet.2015.03.030

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Pd-DHTP触媒を用いた2-クロロフェノールを出発原料とする2,3-二置換ベンゾフランのワンポット合成2017

    • Author(s)
      小澤颯人、山口深雪、眞鍋 敬
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台
    • Related Report
      2016 Annual Research Report
  • [Presentation] 位置選択的反応を指向した新規ヒドロキシ基含有ホスフィン配位子の開発2017

    • Author(s)
      川口智也、山口深雪、眞鍋 敬
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台
    • Related Report
      2016 Annual Research Report
  • [Presentation] 塩化アレーンによる無置換インドールのC-3位選択的C-Hアリール化2016

    • Author(s)
      佐宗裕久、 鈴木康平、山口深雪、眞鍋 敬
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] 基質捕捉部位としてヒドロキシ基を有する新規ホスフィン配位子の開発2016

    • Author(s)
      川口智也、山口深雪、眞鍋 敬
    • Organizer
      第6回CSJ化学フェスタ2016
    • Place of Presentation
      東京
    • Related Report
      2016 Annual Research Report
  • [Presentation] パラジウム-DHTP触媒を用いる二置換ベンゾフランのワンポット合成法の改良2015

    • Author(s)
      秋山知代、山口深雪、眞鍋 敬
    • Organizer
      日本病院薬剤師会東海ブロック・日本薬学会東海支部合同学術大会2015
    • Place of Presentation
      名古屋
    • Year and Date
      2015-11-01
    • Related Report
      2015 Research-status Report
  • [Presentation] C-Hアリール化を鍵段階とするフルオランテン類の合成法の開発2015

    • Author(s)
      樋口麻悠、山口深雪、眞鍋 敬
    • Organizer
      日本病院薬剤師会東海ブロック・日本薬学会東海支部合同学術大会2015
    • Place of Presentation
      名古屋
    • Year and Date
      2015-11-01
    • Related Report
      2015 Research-status Report
  • [Presentation] One-Pot Synthesis of Multisubstituted Benzo[b]furans and Indoles Using Ortho-Selective Cross-Coupling by Palladium-DHTP Catalyst2015

    • Author(s)
      Miyuki Yamaguchi, Haruka Katsumata, Kohei Suzuki, Tomoyo Akiyama, Hirohisa Sasou, Kei Manabe
    • Organizer
      IUPAC-2015 45th World Chemistry Congress
    • Place of Presentation
      韓国・釜山
    • Year and Date
      2015-08-09
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] パラジウム-DHTP触媒を用いる多置換ベンゾフラン類およびインドール類の合成2015

    • Author(s)
      山口深雪、秋山知代、佐宗裕久、勝又はるか、眞鍋 敬
    • Organizer
      第61回日本薬学会東海支部総会・大会
    • Place of Presentation
      名古屋
    • Year and Date
      2015-07-04
    • Related Report
      2015 Research-status Report
  • [Book] Catalyst-controlled Cross-Coupling in "Site-Selective Catalysis" (Takeo Kawabata Ed.)2016

    • Author(s)
      Miyuki Yamaguchi, Kei Manabe
    • Total Pages
      236
    • Publisher
      Splinger International Publishing
    • Related Report
      2015 Research-status Report
  • [Remarks] 静岡県立大学 薬学部 医薬品化学分野

    • URL

      http://w3pharm.u-shizuoka-ken.ac.jp/yakka/

    • Related Report
      2015 Research-status Report

URL: 

Published: 2015-04-16   Modified: 2018-03-22  

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