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Aromatic Carbon-Chlorine Bond Activation Using Heterogeneous Palladium Catalyst

Research Project

Project/Area Number 15K07863
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionDaiichi University, College of Pharmaceutical Sciences (2017)
Gifu Pharmaceutical University (2015-2016)

Principal Investigator

Monguchi Yasunari  第一薬科大学, 薬学部, 教授 (40433205)

Research Collaborator ICHIKAWA Tomohiro  
Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥390,000 (Direct Cost: ¥300,000、Indirect Cost: ¥90,000)
Fiscal Year 2016: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2015: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Keywords不均一系触媒 / クロスカップリング / 芳香族塩素 / パラジウム / 機能性物質 / 触媒化学プロセス / 有機化学 / 合成化学 / 不均一系 / 触媒・化学プロセス
Outline of Final Research Achievements

A heterogeneous palladium catalyst supported on an anion exchange resin bearing N,N-dimethylamino functionalities on the polystyrene-type polymer backbone (7% Pd/WA30) was developed in expectation of the ligand effect of the amino functionalities to the palladium metal. The 7% Pd/WA30 was found to effectively catalyze the Suzuki-Miyaura reaction using less reactive aromatic chlorides owing to the expected function of the amino functionalities as the ligands. The heteroaromatic chlorides, which would suppress the reaction due to the catalytic poisonous property based on the coordination of their heteroatoms to the palladium metals, could also be applied as the substrates. The present reaction is expected to be applied in process chemistry field that is directly connected with drug discovery process due to the prevention of metal contamination since no palladium species was detected in the reaction media.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (15 results)

All 2018 2017 2016 2015 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results) Presentation (11 results) (of which Int'l Joint Research: 2 results,  Invited: 1 results) Remarks (2 results)

  • [Journal Article] A practical method for heterogeneously-catalyzed Mizoroki-Heck reaction: flow system with adjustment of microwave resonance as an energy source2018

    • Author(s)
      Tomohiro Ichikawa, Masahiro Mizuno, Shun Ueda, Noriyuki Ohneda, Hiromichi Odajima, Yoshinari Sawama, Yasunari Monguchi, and Hironao Sajiki
    • Journal Title

      Tetrahedron

      Volume: 74 Issue: 15 Pages: 1810-1816

    • DOI

      10.1016/j.tet.2018.02.044

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of a Unique Heterogeneous Palladium Catalyst for the Suzuki-Miyaura Reaction using (Hetero)aryl Chlorides and Chemoselective Hydrogenation2017

    • Author(s)
      Ichikawa Tomohiro、Netsu Moeko、Mizuno Masahiro、Mizusaki Tomoteru、Takagi Yukio、Sawama Yoshinari、Monguchi Yasunari、Sajiki Hironao
    • Journal Title

      Advanced Synthesis & Catalysis

      Volume: 359 Issue: 13 Pages: 2269-2279

    • DOI

      10.1002/adsc.201700156

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Presentation] 陰イオン交換樹脂担持型パラジウム触媒を利用した不均一系鈴木-宮浦反応による複素環ビアリール骨格の簡便構築法2017

    • Author(s)
      ○市川智大、根津萌子、服部倫弘、澤間善成、門口泰也、佐治木弘尚
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] マイクロ波加熱を利用した不均一系触媒的フロー式溝呂木-Heck反応2017

    • Author(s)
      ○市川智大、水野将弘、上田舜、大根田訓之、小田島博道、澤間善成、門口泰也、佐治木弘尚
    • Organizer
      日本化学会 第97春季年会 (2017)
    • Place of Presentation
      横浜
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] 陰イオン交換樹脂担持型パラジウム触媒の開発研究: イオン交換基とパラジウムの相互作用に基づく特異的触媒活性の発現2017

    • Author(s)
      市川 智大、根津 萌子、水野 将弘、水崎 智照、高木 由紀夫、澤間 善成、門口 泰也、佐治木 弘尚
    • Organizer
      日本プロセス化学会2017サマーシンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 陰イオン交換樹脂担持型パラジウム触媒の開発と担体官能基が触媒活性に及ぼす影響2017

    • Author(s)
      市川 智大、根津 萌子、水野 将弘、水崎 智照、高木 由紀夫、澤間 善成、門口 泰也、佐治木 弘尚
    • Organizer
      日本化学会秋季事業第7回CSJ化学フェスタ
    • Related Report
      2017 Annual Research Report
  • [Presentation] マイクロ波加熱とフロー反応を利用した不均一系触媒的連続溝呂木-Heck 反応2017

    • Author(s)
      市川 智大、水野 将弘、上田 舜、大根田 訓之、小田島 博道、澤間 善成、門口 泰也、佐治木 弘尚
    • Organizer
      第48回中部化学関係学協会支部連合秋季大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 不均一系パラジウム触媒とマイクロ波を利用したフロー式溝呂木- Heck 反応2016

    • Author(s)
      ○市川智大、水野将弘、上田舜、横澤早織、大根田訓之、大野良伸、小田島博道、澤間善成、門口泰也、佐治木弘尚1
    • Organizer
      日本プロセス化学会2016サマーシンポジウム
    • Place of Presentation
      名古屋
    • Year and Date
      2016-07-28
    • Related Report
      2016 Research-status Report
  • [Presentation] 新規機能性を有する環境調和型パラジウム触媒の開発研究:官能基選択的接触還元反応と芳香族塩素化合物の鈴木-宮浦反応2016

    • Author(s)
      ○市川智大、服部倫弘、 澤間善成、 門口泰也、 佐治木弘尚
    • Organizer
      第5回JACI/GSCシンポジウム
    • Place of Presentation
      神戸
    • Year and Date
      2016-06-02
    • Related Report
      2016 Research-status Report
  • [Presentation] Heterogeneous Palladium Catalyst Supported on Anion Exchange Resin for Chemoselective Hydrogenation and Suzuki-Miyaura Reaction of Chloroarenes2015

    • Author(s)
      Tomohiro Ichikawa*, Moeko Netsu, Tomohiro Hattori, Tomoteru Mizusaki, Yoshinari Sawama, Yasunari Monguchi, Hironao Sajiki
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2015)
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 固定化遷移金属触媒:担体素材の性質を利用した有機反応の開発2015

    • Author(s)
      門口泰也
    • Organizer
      第46回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      津
    • Year and Date
      2015-11-07
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] 特徴ある不均一系触媒:陰イオン交換樹脂担持型パラジウムの開発と特異的触媒活性2015

    • Author(s)
      ○市川智大、根津萌子、服部倫弘、澤間善成、門口泰也、佐治木弘尚
    • Organizer
      第108回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2015-11-05
    • Related Report
      2015 Research-status Report
  • [Presentation] Ligand-free Suzuki-Miyaura reaction of chloroarenes catalyzed by anion exchange resin-supported palladium2015

    • Author(s)
      Tomohiro Ichikawa*, Moeko Netsu, Tomohiro Hattori, Yoshinari Sawama, Yasunari Monguchi, Hironao Sajiki
    • Organizer
      International Symposium on Process Chemistry 2015 (ISPC2015)
    • Place of Presentation
      Kyoto, Japan
    • Year and Date
      2015-07-13
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Remarks] 第一薬科大学 薬品化学分野

    • URL

      http://www.daiichi-cps.ac.jp/kenkyu/lab01.html

    • Related Report
      2017 Annual Research Report
  • [Remarks] 岐阜薬科大学 創薬化学大講座 薬品化学研究室

    • URL

      http://sv1.gifu-pu.ac.jp/lab/yakuhin/index.html

    • Related Report
      2016 Research-status Report 2015 Research-status Report

URL: 

Published: 2015-04-16   Modified: 2019-03-29  

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