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Development of electron-deficient phosphine ligands and their application to catalysis

Research Project

Project/Area Number 16K08161
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionKanazawa University

Principal Investigator

Kitamura Masanori  金沢大学, 薬学系, 准教授 (80453835)

Project Period (FY) 2016-10-21 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2018: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2017: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2016: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywordsトリアジン / π電子欠乏性 / リン配位子 / 金属錯体触媒 / 電子欠乏性ホスフィン配位子 / 1,3,5-トリアジン / 触媒反応
Outline of Final Research Achievements

The purpose of this research is to develop highly active metal catalysts ligated by phosphines that are incorporated with triazines, because the triazines are electron-deficient and introduction of substituents on the triazine-ring for electronic tuning is facile. As a result of examining various metal catalysis, reactivity of catalytic reactions especially using tris(triazinyl)phosphines was improved. In addition, it was clarified that the reactivity changes depending on substituents of the triazine ring.

Academic Significance and Societal Importance of the Research Achievements

金属触媒反応は,様々な化合物を作り出すために現代の有機合成化学には欠かせない.電子不足なトリス(トリアジニル)ホスフィンなどを用いて様々な金属触媒反応の検討を行ったところ,より活性な金属触媒を与えることを明らかとした.得られた成果は,金属触媒反応において学術的に重要な知見となると思われ,その波及効果が高いと期待される.また,金属触媒反応は様々な医薬品や材料物質を作りだすため,実用的な面で,その製造コストを削減できると思われる.

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (23 results)

All 2019 2018 2017 2016 Other

All Journal Article (9 results) (of which Peer Reviewed: 9 results,  Open Access: 2 results,  Acknowledgement Compliant: 3 results) Presentation (12 results) (of which Int'l Joint Research: 1 results,  Invited: 2 results) Book (1 results) Remarks (1 results)

  • [Journal Article] Imido-substituted triazines as dehydrative condensing reagents for the chemoselective formation of amides in the presence of free hydroxy?groups2018

    • Author(s)
      Kitamura Masanori、Sasaki Suguru、Nishikawa Riho、Yamada Kohei、Kunishima Munetaka
    • Journal Title

      RSC Advances

      Volume: 8 Issue: 40 Pages: 22482-22489

    • DOI

      10.1039/c8ra03057j

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] An Isolable and Bench-Stable Epoxidizing Reagent Based on Triazine: Triazox2018

    • Author(s)
      Yamada Kohei、Igarashi Yuki、Betsuyaku Tatsuki、Kitamura Masanori、Hirata Koki、Hioki Kazuhito、Kunishima Munetaka
    • Journal Title

      Organic Letters

      Volume: 20 Issue: 7 Pages: 2015-2019

    • DOI

      10.1021/acs.orglett.8b00560

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of highly electron-deficient and less sterically-hindered phosphine ligands possessing 1,3,5-triazinyl groups2018

    • Author(s)
      Kazumi Abe, Masanori Kitamura, Hikaru Fujita, Munetaka Kunishima
    • Journal Title

      Molecular Catalysis

      Volume: 445 Pages: 87-93

    • DOI

      10.1016/j.mcat.2017.11.008

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Novel Alkylating Reagents Designed by the Characteristics of 1,3,5-Triazines2017

    • Author(s)
      Munetaka Kunishima, Kohei Yamada, Hikaru Fujita, Masanori Kitamura
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 75 Issue: 10 Pages: 1023-1034

    • DOI

      10.5059/yukigoseikyokaishi.75.1023

    • NAID

      130006156694

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Study of <i>O</i>-Allylation Using Triazine-Based Reagents2017

    • Author(s)
      Kohei Yamada, Naoko Hayakawa, Hikaru Fujita, Masanori Kitamura, Munetaka Kunishima
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 65 Issue: 1 Pages: 112-115

    • DOI

      10.1248/cpb.c16-00744

    • NAID

      130005187751

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2017 Research-status Report 2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Development of a Triazine-based tert-Butylating Reagent, TriAT-tBu2016

    • Author(s)
      Kohei Yamada, Naoko Hayakawa, Hikaru Fujita, Masanori Kitamura, Munetaka Kunishima
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2016 Issue: 23 Pages: 4093-4098

    • DOI

      10.1002/ejoc.201600663

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Potent triazine-based dehydrocondensing reagents substituted by an amido group2016

    • Author(s)
      Munetaka Kunishima, Daiki Kato, Nobu Kimura, Masanori Kitamura, Kohei Yamada, Kazuhito Hioki
    • Journal Title

      Beilstein J. Org. Chem.

      Volume: 12 Pages: 1897-1903

    • DOI

      10.3762/bjoc.12.179

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Hydroxy and Amino Group-Tolerant Synthesis of Six-Membered Cyclic Quaternary Ammonium Salts Using a Triazine-Based Reagent2016

    • Author(s)
      Masanori Kitamura, Seina Yamamura, Kohei Yamada, Munetaka Kunishima
    • Journal Title

      Asian J. Org. Chem.

      Volume: 5 Issue: 12 Pages: 1508-1517

    • DOI

      10.1002/ajoc.201600429

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Development of Acid-Catalyzed Fluorous Benzylating Reagents Based on a Triazinedione Core2016

    • Author(s)
      Munetaka Kunishima, Ryohei Asao, Kohei Yamada, Masanori Kitamura, Hikaru Fujita
    • Journal Title

      J. Fluorine Chem

      Volume: 190 Pages: 68-74

    • DOI

      10.1016/j.jfluchem.2016.09.003

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] アミノ基を脱離基とした温和なアルキル化反応の開発2019

    • Author(s)
      北岡佑紀,北村正典,藤田光,国嶋崇隆
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] トリアジンジオン骨格を基盤としたアルキル化剤の置換基効果2019

    • Author(s)
      藤井崇徳, 山下莉奈, 藤田光, 角山哲史, 山田耕平, 北村正典, 国嶋崇隆
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] トリアジンを基盤とした単離可能なエポキシ化剤Triazoxの開発2018

    • Author(s)
      別役樹, 五十嵐佑貴, 山田耕平, 北村正典, 平田紘基, 日置和人, 国嶋崇隆
    • Organizer
      日本プロセス化学会 2018 サマーシンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] トリアジンジオン骨格を基盤とした種々アルキル化剤の開発2018

    • Author(s)
      山下莉奈, 藤井崇徳,藤田光, 山田耕平,北村正典, 国嶋崇隆
    • Organizer
      第36回メディシナルケミストリーシンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] トリアジンを基盤とした単離可能なエポキシ化剤Triazoxの開発2018

    • Author(s)
      別役樹, 五十嵐佑貴, 山田耕平, 北村正典, 平田紘基, 日置和人, 国嶋崇隆
    • Organizer
      日本プロセス化学会 2018 ウィンターシンポジウム
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 有機化学と生化学のはざまで2018

    • Author(s)
      北村正典
    • Organizer
      第2回有機合成若手講演会
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] トリアジニルピリジニウム塩を用いたエステル化反応の開発2017

    • Author(s)
      劉杰、山田耕平、北村正典、国嶋崇隆
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台国際センター(宮城県仙台市)
    • Year and Date
      2017-03-25
    • Related Report
      2016 Research-status Report
  • [Presentation] トリアジンジオンを基盤とする新規アシル化剤の開発2017

    • Author(s)
      古田美佳、軽尾友紀子、李政洙、山田耕平、北村正典、国嶋崇隆
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台国際センター(宮城県仙台市)
    • Year and Date
      2017-03-25
    • Related Report
      2016 Research-status Report
  • [Presentation] Development of Electron-Poor Phosphine Ligands Having 1,3,5-Triazinyl Groups2017

    • Author(s)
      Kazumi Abe, Masanori Kitamura, Hikaru Fujita, Munetaka Kunishima
    • Organizer
      26th International Society of Heterocyclic Chemistry
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] 求核触媒を内包した新規エステル化剤の開発2017

    • Author(s)
      劉杰、山田耕平、北村正典、国嶋崇隆
    • Organizer
      第43回反応と合成の進歩シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] 塩化トリアジンを用いた六員環状第四級アンモニウム塩合成法の開発2016

    • Author(s)
      北村正典、山村聖奈、山田耕平、国嶋崇隆
    • Organizer
      第34回メディシナルケミストリーシンポジウム
    • Place of Presentation
      つくば国際会議場(茨城県つくば市)
    • Year and Date
      2016-11-30
    • Related Report
      2016 Research-status Report
  • [Presentation] π電子欠乏性トリアジンを置換基とした電子不足なホスフィン配位子の開発2016

    • Author(s)
      安倍一実、藤田光、北村正典、国嶋崇隆
    • Organizer
      第42回反応と合成の進歩シンポジウム
    • Place of Presentation
      静岡市清水文化会館マリナート(静岡県)
    • Year and Date
      2016-11-07
    • Related Report
      2016 Research-status Report
  • [Book] 医療・診断をささえるペプチド科学 ―再生医療・DDS・診断への応用―(平野 義明 監修)、第3 章 アミド結合形成のための縮合剤2017

    • Author(s)
      北村正典、国嶋崇隆
    • Total Pages
      12
    • Publisher
      シーエムシー出版
    • ISBN
      9784781312675
    • Related Report
      2017 Research-status Report
  • [Remarks] 国嶋研究室ホームページ

    • URL

      http://www.p.kanazawa-u.ac.jp/~bioorg/index.html

    • Related Report
      2018 Annual Research Report

URL: 

Published: 2016-10-24   Modified: 2020-03-30  

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