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Transfer Hydration and Dehydration

Research Project

Project/Area Number 17K05859
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionNagoya University

Principal Investigator

Naka Hiroshi  名古屋大学, 物質科学国際研究センター, 助教 (70431517)

Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2019: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2018: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2017: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywordsニトリル / アミド / 水和 / 脱水 / パラジウム / 水移動型反応 / シアノヒドリン / 水和反応 / ポリアクリロニトリル / 共重合体 / パラジウム触媒 / グルタロニトリル / ヒドロキシアミド / 触媒 / 水 / 脱水反応 / 触媒反応 / 合成化学 / 触媒・化学プロセス / 有機化学
Outline of Final Research Achievements

Interconversion reaction between nitriles and primary amides is an important process in organic synthesis. This report describes the development of palladium-catalyzed transfer hydration of nitriles using carboxamides as a water donor. Successful examples of nitriles include ketone-derived cyanohydrins and glutaronitriles. Also, palladium-catalyzed transfer dehydration of amides to nitriles was demonstrated using electron-deficient nitriles as a water acceptor.

Academic Significance and Societal Importance of the Research Achievements

水の分子間移動を触媒的に制御する「水移動型反応の化学」の提案は,有機化学に新しい考え方をもたらすものと位置付けられる.また,本研究を通して複雑なニトリルとアミドの効率的な合成法を提供することができた.本研究で開発した合成法はすでに物質合成の場面で利用されつつあり,今後も合成化学の進歩に対する貢献が期待できる.以上を通した医薬化学,物質科学,生命科学などの学術領域や精密合成化学産業に対する波及効果が期待できる.

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • 2017 Research-status Report
  • Research Products

    (46 results)

All 2020 2019 2018 2017 Other

All Journal Article (5 results) (of which Peer Reviewed: 4 results) Presentation (37 results) (of which Int'l Joint Research: 15 results,  Invited: 14 results) Remarks (4 results)

  • [Journal Article] Recent Advances in Transfer Hydration of Nitriles with Amides or Aldoximes2020

    • Author(s)
      Naka Hiroshi, Naraoka Asuka
    • Journal Title

      Tetrahedron Letters

      Volume: 61 Issue: 10 Pages: 151557-151557

    • DOI

      10.1016/j.tetlet.2019.151557

    • NAID

      120006869624

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Transfer Hydration of Dinitriles to Dicarboxamides2019

    • Author(s)
      Naraoka Asuka, Naka Hiroshi
    • Journal Title

      Synlett

      Volume: 30 Issue: 17 Pages: 1977-1980

    • DOI

      10.1055/s-0039-1690026

    • NAID

      120006727121

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Acceptor-Controlled Transfer Dehydration of Amides to Nitriles2019

    • Author(s)
      Okabe Hiroyuki、Naraoka Asuka、Isogawa Takahiro、Oishi Shunsuke、Naka Hiroshi
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 12 Pages: 4767-4770

    • DOI

      10.1021/acs.orglett.9b01657

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pd‐Catalyzed β‐Selective C-H Arylation of Thiophenes with Triarylantimony Difluorides2019

    • Author(s)
      Kitamura Yuki、Murata Yuki、Oguri Ayaka、Matsumura Mio、Kakusawa Naoki、Naka Hiroshi、Yasuike Shuji
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 8 Issue: 1 Pages: 138-143

    • DOI

      10.1002/ajoc.201800654

    • NAID

      120006623816

    • Related Report
      2018 Research-status Report
  • [Journal Article] Catalytic Transfer Hydration of Cyanohydrins to α-Hydroxyamides2018

    • Author(s)
      Kanda Tomoya、Naraoka Asuka、Naka Hiroshi
    • Journal Title

      Journal of the American Chemical Society

      Volume: 141 Issue: 2 Pages: 825-830

    • DOI

      10.1021/jacs.8b12877

    • NAID

      120006623815

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] Transfer Hydration of Dinitriles to Diamides2020

    • Author(s)
      Asuka Naraoka, Hiroshi Naka
    • Organizer
      The 3rd IRCCS - The 2nd Reaction Infography Joint International Symposium, Jan 31-Feb 1, 2020, Nagoya University, Nagoya (poster).
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of α-Amino Amides by Transfer Hydration of Nitriles2020

    • Author(s)
      Tomoyo Tamura, Taimeng Liang, Ryoji Noyori, Hiroshi Naka
    • Organizer
      The 3rd IRCCS - The 2nd Reaction Infography Joint International Symposium, Jan 31-Feb 1, 2020, Nagoya University, Nagoya (poster).
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 水移動型反応によるアクロリニトリル-アクリルアミド共重合体の精密合成2020

    • Author(s)
      奈良岡 あすか,有津 拓,内山 峰人,浅井 駿輝,野依 良治,上垣外 正己,中 寛史
    • Organizer
      日本化学会第100春季年会,2020年3月22-25日,東京理科大学,千葉(ポスター).
    • Related Report
      2019 Annual Research Report
  • [Presentation] Palladium-Catalyzed Transfer Hydration of Dinitriles to Diamides2020

    • Author(s)
      Asuka Naraoka, Ryoji Noyori, Hiroshi Naka
    • Organizer
      日本化学会第100春季年会,2020年3月22-25日,東京理科大学,千葉(口頭).
    • Related Report
      2019 Annual Research Report
  • [Presentation] Transfer Hydration of α-Amino Nitriles for Amino Acid Synthesis2020

    • Author(s)
      Tomoyo Tamura, Taimeng Liang, Ryoji Noyori, Hiroshi Naka
    • Organizer
      日本化学会第100春季年会,2020年3月22-25日,東京理科大学,千葉(ポスター).
    • Related Report
      2019 Annual Research Report
  • [Presentation] (Photo)catalytic Conversion of Water and Alcohols for Selective Chemical Synthesis2019

    • Author(s)
      Hiroshi Naka
    • Organizer
      Department Seminar, Nov 19, 2019, Nanjing University of Science and Technology, China (invited).
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Catatlytic Transfer Hydration of Cyanohydrins to alpha-Hydroxyamides2019

    • Author(s)
      Tomoya Kanda, Asuka Naraoka, Hiroshi Naka
    • Organizer
      The 4th International Symposium on Process Chemistry, Jul 24-26, 2019, Kyoto International Conference Center, Kyoto (oral and poster)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Acceptor-controlled Transfer Dehydration of Amides to Nitriles2019

    • Author(s)
      Asuka Naraoka, Hiroyuki, Okabe, Takahiro Isogawa, Shunsuke Oishi, Hiroshi Naka
    • Organizer
      The 4th International Symposium on Process Chemistry, Jul 24-26, 2019, Kyoto International Conference Center, Kyoto (poster).
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of α-Amino Amides by Transfer Hydration of Nitriles2019

    • Author(s)
      Tomoyo Tamura, Taimeng Liang, Ryoji Noyori, Hiroshi Naka
    • Organizer
      統合物質創製化学研究推進機構 第5回国内シンポジウム 物質創製化学のフロンティア,2019年11月18-19日,北海道大学,北海道(ポスター).
    • Related Report
      2019 Annual Research Report
  • [Presentation] 人の生き方を変える化学2019

    • Author(s)
      中 寛史
    • Organizer
      名古屋市立向陽高校模擬授業,2019年10月31日,向陽高校,名古屋(招待).
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] 水とアルコールを使った(光)触媒的合成化学2019

    • Author(s)
      中 寛史
    • Organizer
      京大人環物質機能相関論セミナー,2019年10月16日,京都大学,京都(招待).
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] 触媒的水移動型水和反応による α-アミノアミドの迅速合成2019

    • Author(s)
      田村 知世,野依 良治,中 寛史
    • Organizer
      第 36 回有機合成化学セミナー,2019年9月17-19日,長良川国際会議場,岐阜(ポスター).
    • Related Report
      2019 Annual Research Report
  • [Presentation] 水移動型水和反応によるジアミド合成2019

    • Author(s)
      中 寛史
    • Organizer
      AIKOC-3,2019年8月31日,大阪大学,大阪(ポスター).
    • Related Report
      2019 Annual Research Report
  • [Presentation] 新しい化学反応を使って未知のアミノ酸をつくる!2019

    • Author(s)
      田村 知世,野依 良治,中 寛史
    • Organizer
      名古屋大学若手女性研究者サイエンスフォーラム,2019年7月17日,名古屋大学,名古屋(ポスター).
    • Related Report
      2019 Annual Research Report
  • [Presentation] 触媒的水移動型水和反応による α-アミノアミドの迅速合成2019

    • Author(s)
      田村 知世,野依 良治,中 寛史
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Research-status Report
  • [Presentation] ニトリルの触媒的水移動型水和反応の開発2019

    • Author(s)
      奈良岡 あすか, 神田 智哉, 田村 知世,野依 良治,中 寛史
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Research-status Report
  • [Presentation] パラジウム触媒を用いた水移動型水和反応の反応機構2019

    • Author(s)
      奈良岡 あすか, 神田 智哉, 中 寛史
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] Transfer (De)hydration Catalysis2019

    • Author(s)
      Hiroshi Naka
    • Organizer
      Core-to-Core Symposium “Elements Function for Transformative Catalysis and Materials”
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] (Photo)catalytic Conversion of Water and Alcohols for Selective Chemical Synthesis2019

    • Author(s)
      Hiroshi Naka
    • Organizer
      Chemistry Department Seminar, Jan 31, 2019, Dalhousie University, Canada
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] (Photo)catalytic Conversion of Water and Alcohols for Selective Chemical Synthesis2019

    • Author(s)
      Hiroshi Naka
    • Organizer
      McGill Chemical Society Seminar, Jan 30, 2019, McGill University, Canada
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] (Photo)catalytic Conversion of Water and Alcohols for Selective Chemical Synthesis2019

    • Author(s)
      Hiroshi Naka
    • Organizer
      Chemistry Department Seminar, Jan 28, 2019, Queen’s University, Canada
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] (Photo)catalytic Conversion of Water and Alcohols for Selective Chemical Synthesis2019

    • Author(s)
      Hiroshi Naka
    • Organizer
      The 2nd International Symposium of IRCCS, Jan 25-26, 2019, Kyoto University, Kyoto
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] (Photo)catalytic Conversion of Water and Alcohols for Selective Chemical Synthesis2019

    • Author(s)
      Hiroshi Naka
    • Organizer
      Special Department Seminar, Jan 25, 2019, University of Ottawa, Canada
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] (Photo)catalytic Conversion of Water and Alcohols for Selective Chemical Synthesis2019

    • Author(s)
      Hiroshi Naka
    • Organizer
      Special Chemistry Seminar, Jan 24, 2019, University of Toronto, Canada
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] (Photo)catalytic Conversion of Water and Alcohols for Selective Chemical Synthesis2019

    • Author(s)
      Hiroshi Naka
    • Organizer
      Department Seminar, Jan 23, 2019, University of Alberta, Canada
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] (Photo)catalytic Conversion of Water and Alcohols for Selective Chemical Synthesis2019

    • Author(s)
      Hiroshi Naka
    • Organizer
      Organic Seminar, Jan 21, 2019, University of British Colombia, Canada
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Palladium-Catalyzed Transfer Hydration of Cyanohydrins2019

    • Author(s)
      Asuka Naraoka, Tomoya Kanda, Hiroshi Naka
    • Organizer
      The 2nd International Symposium of IRCCS
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] 水とアルコールを使った(光)触媒的合成化学2018

    • Author(s)
      中 寛史
    • Organizer
      京大人環 分子環境相関論ウインターセミナー2018
    • Related Report
      2018 Research-status Report
  • [Presentation] Transfer Hydration of Cyanohydrins2018

    • Author(s)
      Hiroshi Naka, Tomoya Kanda, Asuka Naraoka, Ryoji Noyori
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-14),
    • Related Report
      2018 Research-status Report
  • [Presentation] 水の分子変換化学2018

    • Author(s)
      中 寛史
    • Organizer
      講演会~分子変換の深化~
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] シアノヒドリンの水移動型水和反応によるa-ヒドロキシアミドの合成2018

    • Author(s)
      神田 智哉,野依 良治,中 寛史
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Research-status Report
  • [Presentation] シアノヒドリンの水移動型水和反応2018

    • Author(s)
      神田 智哉,野依 良治,中 寛史
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] Transfer Dehydration of Primary Amides Using Electron-Deficient Nitriles2018

    • Author(s)
      Hiroyuki Okabe, Takahiro Isogawa, Asuka Naraoka, Ryoji Noyori, Hiroshi Naka
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 電子不足ニトリルを用いた一級カルボン酸アミドの水移動型脱水反応2018

    • Author(s)
      岡部 弘幸,五十川 貴裕,奈良岡 あすか,野依 良治,中 寛史
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 水で有機物質をつくる2017

    • Author(s)
      中 寛史
    • Organizer
      JPIJS 関西地区討論会
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] パラジウム触媒と電子不足ニトリルを用いた一級アミドの水中脱水反応2017

    • Author(s)
      岡部 弘幸,五十川 貴裕,野依 良治,中 寛史
    • Organizer
      第34回有機合成化学セミナー
    • Related Report
      2017 Research-status Report
  • [Presentation] 水で有機物質をつくる2017

    • Author(s)
      中 寛史
    • Organizer
      バイオ元素戦略懇談会
    • Related Report
      2017 Research-status Report
  • [Remarks] Naka Reserach Group

    • URL

      http://noy.chem.nagoya-u.ac.jp/H_Naka-J/

    • Related Report
      2019 Annual Research Report
  • [Remarks] 研究グループ

    • URL

      http://noy.chem.nagoya-u.ac.jp/H_Naka-J/

    • Related Report
      2018 Research-status Report
  • [Remarks] 野依特別研究室

    • URL

      http://noy.chem.nagoya-u.ac.jp/noy_j/

    • Related Report
      2018 Research-status Report
  • [Remarks] 化学科での論文紹介記事

    • URL

      http://www3.chem.nagoya-u.ac.jp/wordpress/?p=11732

    • Related Report
      2018 Research-status Report

URL: 

Published: 2017-04-28   Modified: 2021-02-19  

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