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Development of novel substrate-recognizable catalysts utilizing reversible formation of covalent bonds

Research Project

Project/Area Number 23790016
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

KONISHI Hideyuki  静岡県立大学, 薬学部, 助教 (20565618)

Co-Investigator(Renkei-kenkyūsha) MANABE Kei  静岡県立大学, 薬学部, 教授 (00251439)
Project Period (FY) 2011-04-28 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2014: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2013: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2012: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2011: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Keywords共有結合 / 基質認識 / ボロン酸 / ヒドロキシ基 / ヒドロエステル化 / 触媒
Outline of Final Research Achievements

With expectation for a covalent bond to have strong interaction with substrates, novel catalysts that enabled formation and dissociation of covalent bonds were designed and synthesized. Application of these catalysts to catalytic organic reactions was also investigated. A ligand bearing boronic acid moiety was synthesized and could be, in principle, applicable to catalytic organic reactions by utilizing formation of boronic acid esters with alcohols. Furthermore, ester exchange strategy using an alcohol could work well in broadening of substrate generality to a great extent in Ru-catalyzed hydroesterification of alkenes using formates. Experimental mechanistic studies revealed for the first time the existence of multiple reaction pathways in the hydroesterification.

Report

(5 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • 2011 Research-status Report
  • Research Products

    (45 results)

All 2015 2014 2013 2012 Other

All Journal Article (14 results) (of which Peer Reviewed: 11 results,  Acknowledgement Compliant: 1 results) Presentation (29 results) Remarks (2 results)

  • [Journal Article] Concise Synthesis of Cyclic Carbonyl Compounds from Haloarenes Using Phenyl Formate as the Carbonyl Source2015

    • Author(s)
      Hideyuki Konishi, Hiroki Nagase, Kei Manabe
    • Journal Title

      Chemical Communications

      Volume: 51 Issue: 10 Pages: 1854-1857

    • DOI

      10.1039/c4cc09413a

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Imidazole Derivatives as Accelerators for Ruthenium-Catalyzed Hydroesterification and Hydrocarbamoylation of Alkenes: Extensive Ligand Screening and Mechanistic Study2015

    • Author(s)
      Hideyuki Konishi, Takashi Muto, Tsuyoshi Ueda, Yayoi Yamada, Miyuki Yamaguchi, Kei Manabe
    • Journal Title

      ChemCatChem

      Volume: 7 Issue: 5 Pages: 836-845

    • DOI

      10.1002/cctc.201402986

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 毒性の一酸化炭素ガスを使わない化学合成法2014

    • Author(s)
      小西英之、眞鍋敬
    • Journal Title

      ファルマシア

      Volume: 50 Pages: 310-314

    • NAID

      130005154890

    • Related Report
      2014 Annual Research Report
  • [Journal Article] Formic Acid Derivatives as Practical Carbon Monoxide Surrogates for Metal-Catalyzed Carbonylation Reactions2014

    • Author(s)
      Hideyuki Konishi, Kei Manabe
    • Journal Title

      Synlett

      Volume: 25 Issue: 14 Pages: 1971-1986

    • DOI

      10.1055/s-0033-1339136

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 新規一酸化炭素等価体を用いる実用的カルボニル化反応の開発2014

    • Author(s)
      小西英之、眞鍋敬
    • Journal Title

      Wako Organic Square

      Volume: 49 Pages: 2-4

    • Related Report
      2014 Annual Research Report
  • [Journal Article] Pd-Catalyzed External-CO-Free Carbonylation: Preparation of 2,4,6-Trichlorophenyl 3,4-Dihydronaphthalene-2-Carboxylate2014

    • Author(s)
      Hideyuki Konishi, Tsuyoshi Ueda, Kei Manabe
    • Journal Title

      Organic Syntheses

      Volume: 90 Pages: 39-51

    • DOI

      10.15227/orgsyn.091.0039

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] 毒性の一酸化炭素ガスを用いない化学合成法2014

    • Author(s)
      小西英之、眞鍋敬
    • Journal Title

      ファルマシア

      Volume: 50 Pages: 310-314

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] マンガンを用いる有機合成反応2014

    • Author(s)
      小西英之
    • Journal Title

      化学と教育

      Volume: 62 Pages: 250-253

    • Related Report
      2013 Research-status Report
  • [Journal Article] Palladium-Catalyzed Reductive Carbonylation of Aryl Halides with N-Formylsaccharin as a CO Source2013

    • Author(s)
      Tsuyoshi Ueda, Hideyuki Konishi, Kei Manabe
    • Journal Title

      Angewandte Chemie, International Edition

      Volume: 52 Issue: 33 Pages: 8611-8615

    • DOI

      10.1002/anie.201303926

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Fluorocarbonylation Using N-Formylsaccharin as CO Source: General Access to Carboxylic Acid Derivatives2013

    • Author(s)
      Tsuyoshi Ueda, Hideyuki Konishi, Kei Manabe
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 20 Pages: 5370-5373

    • DOI

      10.1021/ol4026815

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Carbonylation of Aryl, Alkenyl, and Allyl Halides with Phenyl Formate2012

    • Author(s)
      Tsuyoshi Ueda, Hideyuki Konishi, Kei Manabe
    • Journal Title

      Organic Letters

      Volume: 14 Issue: 12 Pages: 3100-3103

    • DOI

      10.1021/ol301192s

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Preparation of alpha,beta-Unsaturated Esters and Amides via External-CO-Free Palladium-Catalyzed Carbonylation of Alkenyl Tosylates2012

    • Author(s)
      Tsuyoshi Ueda, Hideyuki Konishi, Kei Manabe
    • Journal Title

      Tetrahedron Letters

      Volume: 53 Issue: 38 Pages: 5171-5175

    • DOI

      10.1016/j.tetlet.2012.07.057

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Remarkable Improvement Achieved by Imidazole Derivatives in Ruthenium-Catalyzed Hydroesterification of Alkenes Using Formates2012

    • Author(s)
      Hideyuki Konishi, Tsuyoshi Ueda, Takashi Muto, Kei Manabe
    • Journal Title

      Organic Letters

      Volume: 14 Issue: 18 Pages: 4722-4725

    • DOI

      10.1021/ol301850y

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Trichlorophenyl Formate: Highly Reactive and Easily Accessible Crystalline CO Surrogate for Palladium-Catalyzed Carbonylation of Aryl/Alkenyl Halides and Triflates2012

    • Author(s)
      Tsuyoshi Ueda, Hideyuki Konishi, Kei Manabe
    • Journal Title

      Organic Letters

      Volume: 14 Issue: 20 Pages: 5370-5373

    • DOI

      10.1021/ol302593z

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] Mechanistic study on the generation of carbon monoxide from phenyl formate and its application to the development of Pd-catalyzed carbonylation at room temperature2015

    • Author(s)
      Hideyuki Konishi, Mika Matsubara, Keisuke Mori, Yoshinobu Ishikawa, Hiroshi Hashimoto, Hiroaki Tokiwa, Kei Manabe
    • Organizer
      The International Chemical Congress of Pacific Basin Societies (Pacifichem 2015)
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2015-12-15 – 2015-12-20
    • Related Report
      2014 Annual Research Report
  • [Presentation] Pd触媒を用いる環状スルホンアミドおよびスルフィンアミド類の一段階合成法の開発2015

    • Author(s)
      田中寛康、小西英之、眞鍋敬
    • Organizer
      第61回日本薬学会東海支部大会
    • Place of Presentation
      名古屋
    • Year and Date
      2015-07-04
    • Related Report
      2014 Annual Research Report
  • [Presentation] ギ酸フェニルを一酸化炭素源として用いる環状カルボニル化合物の新規合成法の開発2015

    • Author(s)
      長瀬浩揮、小西英之、眞鍋敬
    • Organizer
      第13回次世代を担う有機化学シンポジウム
    • Place of Presentation
      草津
    • Year and Date
      2015-05-22 – 2015-05-23
    • Related Report
      2014 Annual Research Report
  • [Presentation] Pd触媒を用いる環状スルホンアミドおよびスルフィンアミド類新規合成法の開発2015

    • Author(s)
      田中寛康、小西英之、眞鍋敬
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸
    • Year and Date
      2015-03-26 – 2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] ギ酸フェニル分解反応における速度論的検討および室温条件下でのカルボニル化反応への応用2015

    • Author(s)
      松原美香、小西英之、眞鍋敬
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸
    • Year and Date
      2015-03-26 – 2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 芳香族ギ酸エステルを用いる環状カルボニル化合物の効率的合成法の開発2015

    • Author(s)
      長瀬浩揮、小西英之、眞鍋敬
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸
    • Year and Date
      2015-03-26 – 2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] ギ酸誘導体の一酸化炭素生成機構およびこれを用いる実用的有機合成反応2014

    • Author(s)
      小西英之、上田剛、松原美香、森敬介、石川吉伸、橋本博、常盤広明、眞鍋敬
    • Organizer
      第40回反応と合成の進歩シンポジウム
    • Place of Presentation
      仙台
    • Year and Date
      2014-11-10 – 2014-11-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] Pd触媒を用いる環状スルホンアミドおよびスルフィンアミド類新規合成法の開発2014

    • Author(s)
      田中寛康、小西英之、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2014
    • Place of Presentation
      静岡
    • Year and Date
      2014-11-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] 軸不斉含有ジカルボン酸エステルの効率的合成法の開発2014

    • Author(s)
      星野史佳、小西英之、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2014
    • Place of Presentation
      静岡
    • Year and Date
      2014-11-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] Pd-Catalyzed Carbonylative Transformations Using Formic Acid Derivatives as Practical Carbon Monoxide Surrogates2014

    • Author(s)
      Hideyuki Konishi, Kei Manabe
    • Organizer
      The 14th Tateshina Conference on Organic Chemistry
    • Place of Presentation
      Tateshina, Japan
    • Year and Date
      2014-11-07 – 2014-11-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] ギ酸誘導体を一酸化炭素源として用いる環状カルボニル化合物の新規合成法の開発2014

    • Author(s)
      長瀬浩揮、小西英之、眞鍋敬
    • Organizer
      日本プロセス化学会2014サマーシンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2014-07-31 – 2014-08-01
    • Related Report
      2014 Annual Research Report
  • [Presentation] 塩基によるギ酸エステルの分解反応の計算化学的解析2014

    • Author(s)
      森敬介、小西英之、石川吉伸、橋本博、常盤広明、眞鍋敬
    • Organizer
      第60回日本薬学会東海支部大会
    • Place of Presentation
      鈴鹿
    • Year and Date
      2014-07-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] ギ酸誘導体を一酸化炭素源として用いる新規有機合成反応の開発2014

    • Author(s)
      小西英之、上田剛、王晰、長瀬浩揮、眞鍋敬
    • Organizer
      第105回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2014-06-10 – 2014-06-11
    • Related Report
      2014 Annual Research Report 2013 Research-status Report
  • [Presentation] ギ酸フェニルの分解反応における速度論的検討およびパラジウム触媒的カルボニル化反応への応用2014

    • Author(s)
      松原美香、小西英之、眞鍋敬
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本
    • Related Report
      2013 Research-status Report
  • [Presentation] 山田弥生、武藤崇、山口深雪、小西英之、眞鍋敬2014

    • Author(s)
      Ru触媒を用いるアルケンの位置選択的ヒドロエステル化反応の開発および反応機構の解明
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本
    • Related Report
      2013 Research-status Report
  • [Presentation] ギ酸誘導体を用いるハロゲン化ビアリールのPd触媒的シクロカルボニル化反応の開発2014

    • Author(s)
      王晰、小西英之、眞鍋敬
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本
    • Related Report
      2013 Research-status Report
  • [Presentation] ギ酸エステルを用いる環状カルボニル化合物の新規合成法の開発2014

    • Author(s)
      長瀬浩揮、小西英之、眞鍋敬
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本
    • Related Report
      2013 Research-status Report
  • [Presentation] o,o,p-オリゴフェニレンの合成と計算化学的手法による立体配座解析2013

    • Author(s)
      森敬介、木村武志、橋爪大輔、小西英之、眞鍋敬
    • Organizer
      第59回日本薬学会東海支部総会・大会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] ギ酸フェニルの分解反応における速度論的検討2013

    • Author(s)
      松原美香、小西英之、眞鍋敬
    • Organizer
      第59回日本薬学会東海支部総会・大会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] Aryl Formates as CO Surrogates for Practical Pd-Catalyzed Carbonylation2013

    • Author(s)
      Hideyuki Konishi, Tsuyoshi Ueda, Mika Matsubara, Kei Manabe
    • Organizer
      17th International IUPAC Conference on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-17)
    • Place of Presentation
      Ft. Collins, USA
    • Related Report
      2013 Research-status Report
  • [Presentation] 基質結合部位としてボロン酸部位を持つ新規配位子の創製2013

    • Author(s)
      大月萌、細野礼貴、武藤崇、小西英之、眞鍋敬
    • Organizer
      第44回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      浜松
    • Related Report
      2013 Research-status Report
  • [Presentation] ギ酸エステルを用いるハロゲン化ビアリールの触媒的シクロカルボニル化反応の開発2013

    • Author(s)
      王晰、小西英之、眞鍋敬
    • Organizer
      第44回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      浜松
    • Related Report
      2013 Research-status Report
  • [Presentation] ギ酸エステルの分解による一酸化炭素生成反応の計算化学的解析2013

    • Author(s)
      森敬介、小西英之、石川吉伸、橋本博、眞鍋敬
    • Organizer
      第44回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      浜松
    • Related Report
      2013 Research-status Report
  • [Presentation] ギ酸フェニルの分解反応における速度論的検討と触媒的カルボニル化反応への応用2013

    • Author(s)
      松原美香、小西英之、眞鍋敬
    • Organizer
      第44回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      浜松
    • Related Report
      2013 Research-status Report
  • [Presentation] 芳香族ハライド、ギ酸エステル、求核剤を用いる新規芳香族ケトン合成法の開発2013

    • Author(s)
      長瀬浩揮、小西英之、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2013
    • Place of Presentation
      鈴鹿
    • Related Report
      2013 Research-status Report
  • [Presentation] ルテニウム-イミダゾール触媒系を用いる分子内ヒドロエステル化反応2012

    • Author(s)
      上田剛、小西英之、眞鍋敬
    • Organizer
      日本プロセス化学会2012サマーシンポジウム
    • Place of Presentation
      京都
    • Related Report
      2012 Research-status Report
  • [Presentation] ギ酸フェニル類を用いたPd触媒による実用的COフリーカルボニル化反応2012

    • Author(s)
      上田剛、小西英之、眞鍋敬
    • Organizer
      第29回有機合成化学セミナー
    • Place of Presentation
      静岡
    • Related Report
      2012 Research-status Report
  • [Presentation] Development of Novel Catalytic Organic Reactions Utilizing Formic Acid Esters2012

    • Author(s)
      Hideyuki Konishi, Tsuyoshi Ueda, Kei Manabe
    • Organizer
      The 6th Takeda Science Foundation Symposium on Pharmasciences
    • Place of Presentation
      Osaka
    • Related Report
      2012 Research-status Report
  • [Presentation] ギ酸エステルを基質とする新規触媒的有機合成反応の開発2012

    • Author(s)
      小西英之、上田剛、武藤崇、眞鍋敬
    • Organizer
      第102回有機合成シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2012 Research-status Report
  • [Remarks] 静岡県立大学薬学部 医薬品化学分野・薬化学講座 ホームページ

    • URL

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

    • Related Report
      2014 Annual Research Report
  • [Remarks] 静岡県立大学薬学部 医薬品化学分野・薬化学講座

    • URL

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

    • Related Report
      2013 Research-status Report

URL: 

Published: 2011-08-05   Modified: 2019-07-29  

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