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Development of environmentally benign and efficient flow organic transformations using carbon dioxide

Research Project

Project/Area Number 16K05876
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Green/Environmental chemistry
Research InstitutionInstitute for Molecular Science

Principal Investigator

OSAKO Takao  分子科学研究所, 生命・錯体分子科学研究領域, 助教 (90500984)

Research Collaborator UOZUMI Yasuhiro  
Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywords担持遷移金属触媒 / フロー反応 / 二酸化炭素 / 両親媒性ポリマー / 遷移金属触媒 / 触媒・化学プロセス / 合成化学 / フロー合成 / 担持触媒
Outline of Final Research Achievements

We have developed amphiphilic polymer-supported transition-metal catalysts that efficiently promoted organic transformations using carbon dioxide and applied them to continuous flow systems. As the results, we successfully found that a supported silver catalyst promoted the cyclization of propargyl alcohols with carbon dioxide under batch and flow conditions. In addition, we also developed the efficient organic transformations including carbonylation of aryl halides with carbon monoxide, azide-alkyne cycloaddition, selective aerobic oxidation of primary benzylic alcohols, and asymmetric 1,4-addition with the polymer-supported transition-metal catalysts.

Academic Significance and Societal Importance of the Research Achievements

本研究課題の成果として、二酸化炭素を炭素源として用いる有機分子変換反応を効率的に促進する両親媒性ポリマー担持遷移金属触媒の開発およびその反応のフロー工程化を実現し、フロー工程での遷移金属触媒による二酸化炭素を用いた有機分子変換反応工程の確立に関しての重要な知見を得ることができた。このような成果は、二酸化炭素の有益な化合物への効率的変換工程を確立するのみならず、我々が直面している二酸化炭素の排出問題の解決に関する方法論の提供にも繋がることが期待され、その学術的および社会的意義は大きいものである。

Report

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

    (34 results)

All 2019 2018 2017 2016 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results,  Acknowledgement Compliant: 2 results) Presentation (22 results) (of which Int'l Joint Research: 1 results,  Invited: 2 results) Remarks (2 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Aqueous Flow Hydroxycarbonylation of Aryl Halides Catalyzed by an Amphiphilic Polymer-Supported Palladium Diphenylphosphine Catalyst2019

    • Author(s)
      Takao Osako, Reinhard Kaiser, Kaoru Torii, Yasuhiro Uozumi
    • Journal Title

      Synlett

      Volume: 30 Issue: 08 Pages: 961-966

    • DOI

      10.1055/s-0037-1611769

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Copper-Catalyzed C(sp)-H Bond Insertion of Carbenoids Derived from N-Tosylhydrazones2018

    • Author(s)
      Uozumi Yasuhiro、Osako Takao、Nagaosa Makoto、Hamasaka Go
    • Journal Title

      Synlett

      Volume: 29 Issue: 17 Pages: 2251-2256

    • DOI

      10.1055/s-0037-1611003

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Controlled Aerobic Oxidation of Primary Benzylic Alcohols to Aldehydes Catalyzed by Polymer-Supported Triazine-Based Dendrimer-Copper Composites2018

    • Author(s)
      Uozumi Yasuhiro、Pan Shiguang、Yan Shuo、Osako Takao
    • Journal Title

      Synlett

      Volume: 29 Issue: 09 Pages: 1152-1156

    • DOI

      10.1055/s-0036-1591981

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Aqueous Asymmetric 1,4-Addition of Arylboronic Acids to Enones Catalyzed by an Amphiphilic Resin-Supported Chiral Diene Rhodium Complex under Batch and Continuous-Flow Conditions2018

    • Author(s)
      Shen Guanshuo、Osako Takao、Nagaosa Makoto、Yasuhiro Uozumi
    • Journal Title

      J. Org. Chem.

      Volume: - Issue: 14 Pages: 7380-7387

    • DOI

      10.1021/acs.joc.8b00178

    • Related Report
      2018 Annual Research Report 2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Batch and Continuous-Flow Huisgen 1,3-Dipolar Cycloadditions with an Amphiphilic Resin-Supported Triazine-Based Polyethyleneamine Dendrimer Copper Catalyst2017

    • Author(s)
      Pan Shiguang、Yan Shuo、Osako Takao、Uozumi Yasuhiro
    • Journal Title

      ACS Sustainable Chem. Eng.

      Volume: 5 Issue: 11 Pages: 10722-10734

    • DOI

      10.1021/acssuschemeng.7b02646

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Chemoselective Continuous-Flow Hydrogenation of Aldehydes Catalyzed by Platinum Nanoparticles Dispersed in an Amphiphilic Resin2017

    • Author(s)
      Osako Takao、Torii Kaoru、Hirata Shuichi、Uozumi Yasuhiro
    • Journal Title

      ACS Catal.

      Volume: 7 Issue: 10 Pages: 7371-7377

    • DOI

      10.1021/acscatal.7b02604

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Application of Heterogeneous Polymer-Supported Catalysts to Continuous Flow Systems2016

    • Author(s)
      T. Osako, Y. M. A. Yamada and Y. Uozumi
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 74 Issue: 6 Pages: 621-630

    • DOI

      10.5059/yukigoseikyokaishi.74.621

    • NAID

      130005164588

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 2.Recyclable Polystyrene-Supported Copper Catalysts for the Aerobic Oxidative Homocoupling of Terminal Alkynes2016

    • Author(s)
      Shuo Yan, Shiguang Pan, Takao Osako, Yasuhiro Uozumi
    • Journal Title

      Synlett

      Volume: 27 Issue: 08 Pages: 1232-1236

    • DOI

      10.1055/s-0035-1561361

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Efficient and Green Synthesis of Propargylamines via A3 and KA2 Coupling Reactions Catalyzed by Polymer-Supported Copper(II)-Bipyridine Complex2019

    • Author(s)
      Shiguang Pan, Shuo Yan, Takao Osako, Yasuhiro Uozumi
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 両親媒性ポリマー担持プラチナナノ触媒によるアルデヒドの化学選択的水中フロー水素化反応2018

    • Author(s)
      大迫隆男・鳥居薫・平田修一・魚住泰広
    • Organizer
      第65回有機金属化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Aqueous Asymmetric 1,4-Addition Catalyzed by an Amphiphilic Resin-Supported Chiral Diene Rhodium Complex2018

    • Author(s)
      Guanshuo Shen, Takao Osako, Makoto Nagaosa, Yasuhiro Uozumi
    • Organizer
      第65回有機金属化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Asymmetric 1,4-Addition of Arylboronic Acids to Enones Catalyzed by an Amphiphilic Resin-Supported Homochiral Diene Rhodium Complex in Water2018

    • Author(s)
      Takao Osako, Guanshuo Shen, Makoto Nagaosa, Yasuhiro Uozumi
    • Organizer
      The 43rd International Conference on Coordination Chemistry(ICCC2018)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 両親媒性ポリマー担持プラチナナノ触媒を用いたアルデヒドの化学選択的水中フロー水素化反応2018

    • Author(s)
      沈冠碩・大迫隆男・永長誠・魚住泰広
    • 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] 両親媒性ポリマー担持プラチナナノ触媒を用いたアルデヒドの化学選択的水中フロー水素化反応2018

    • Author(s)
      大迫隆男・鳥居薫・平田修一・魚住泰広
    • 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] Selective Aerobic Oxidation of Benzyl Bromides to Benzaldehydes With a Polymer-Supported Copper Catalyst2018

    • Author(s)
      Takao Osako, Tatsushi Tsuchimoto, Aya Tazawa, Yasuhiro Uozumi
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] Asymmetric 1,4-Addition of Arylboronic Acids to Enones Catalyzed by an Amphiphilic Resin-Supported Homochiral Diene Rhodium Complex in Water2018

    • Author(s)
      Guanshuo Shen, Takao Osako, Makoto Nagaosa, Yasuhiro Uozumi
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] パラジウム触媒によるホルムアミドアセタールを用いた芳香族ハライドのアミノカルボニル化2018

    • Author(s)
      平田修一、大迫隆男、魚住泰広
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 両親媒性ポリマー担持プラチナナノ触媒を用いたアルデヒドの選択的水中フロー水素化反応2017

    • Author(s)
      大迫隆男・鳥居 薫・平田修一・魚住泰広
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應大学、神奈川県横浜市
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] Huisgen 1,3-Dipolar Cycloaddition in Water with An Amphiphilic Resin-Supported Triazine-Based Dendrimer-Copper Catalyst2017

    • Author(s)
      Shiguang Pan, Shuo Yan, Takao Osako, Yasuhiro Uozumi
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應大学、神奈川県横浜市
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] グリーン・サスティナブル有機分子変換反応の実現を目指し銅触媒の開発2017

    • Author(s)
      大迫隆男
    • Organizer
      愛媛大学工学部応用化学科第232回応用化学科セミナー
    • Place of Presentation
      愛媛大学、愛媛県松山市
    • Year and Date
      2017-01-20
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] 効率的な酸素酸化および水素化を実現する両親媒性ポリマー担持Ptナノ触媒を用いたフロー反応システムの開発2017

    • Author(s)
      魚住泰広・大迫隆男
    • Organizer
      創造機能化学第116委員会
    • Related Report
      2017 Research-status Report
  • [Presentation] 両親媒性ポリマー担持プラチナナノ触媒を用いたアルデヒド選択的フロー水素化反応2017

    • Author(s)
      大迫隆男
    • Organizer
      第4回辰巳午化学シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] パラジウム触媒によるホルムアミドアセタールを用いた芳香族ハロゲン化物のアミノカルボニル化2017

    • Author(s)
      平田修一、大迫隆男、魚住泰広
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] ポリマー担持銅触媒を用いたベンジルブロミドのベンズアルデヒドへの選択的酸素酸化反応2017

    • Author(s)
      大迫隆男、土本達司、田澤文、魚住泰広
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 両親媒性ポリマー担持遷移金属触媒の最新成果:プラチナナノ触媒による選択的フロー水素化反応および新規両親媒性ポリマー担持銅触媒の開発2017

    • Author(s)
      大迫隆男
    • Organizer
      第3回魚住触媒研究会
    • Related Report
      2017 Research-status Report
  • [Presentation] Aerobic Oxidation of Benzylic Alcohols Catalyzed by Polymer-Supported Dendrimer-Copper Catalysts2016

    • Author(s)
      Shuo Yan, Shiguang Pan, Takao Osako, Yasuhiro Uozumi
    • Organizer
      第63回有機金属化学討論会
    • Place of Presentation
      早稲田大学、東京都新宿区
    • Year and Date
      2016-09-14
    • Related Report
      2016 Research-status Report
  • [Presentation] An Amphiphilic Resin-Supported Triazine-Based Dendrimer-Copper Catalyst for Huisgen 1,3-Dipolar Cycloaddition in Water2016

    • Author(s)
      Shiguang Pan, Shuo Yan, Takao Osako, Yasuhiro Uozumi
    • Organizer
      第63回有機金属化学討論会
    • Place of Presentation
      早稲田大学、東京都新宿区
    • Year and Date
      2016-09-14
    • Related Report
      2016 Research-status Report
  • [Presentation] グリーン・サステナブル銅触媒反応システムの開発を目指して2016

    • Author(s)
      大迫隆男
    • Organizer
      第3回辰巳午化学シンポジウム
    • Place of Presentation
      広島大学、広島県東広島市
    • Year and Date
      2016-08-27
    • Related Report
      2016 Research-status Report
  • [Presentation] 効率的な酸素酸化および還元反応を実現する両親媒性ポリマー担持プラチナナノ触媒を用いたフロー反応システムの開発2016

    • Author(s)
      大迫隆男・鳥居 薫・田澤 文・魚住泰広
    • Organizer
      日本プロセス化学会2016 サマーシンポジウム
    • Place of Presentation
      名古屋国際会議場、愛知県名古屋市
    • Year and Date
      2016-07-28
    • Related Report
      2016 Research-status Report
  • [Presentation] 両親媒性ポリマー担持プラチナナノ触媒によるフロー酸素酸化および還元反応2016

    • Author(s)
      大迫隆男・鳥居 薫・田澤 文・魚住泰広
    • Organizer
      第5回JACI/GSCシンポジウム
    • Place of Presentation
      ANAクラウンプラザホテル神戸、兵庫県神戸市
    • Year and Date
      2016-06-02
    • Related Report
      2016 Research-status Report
  • [Remarks] 分子科学研究所 魚住研究室

    • URL

      https://groups.ims.ac.jp/organization/uozumi_g/index.html

    • Related Report
      2018 Annual Research Report
  • [Remarks] 分子科学研究所 魚住研究室

    • URL

      https://groups.ims.ac.jp/organization/uozumi_g/index.html

    • Related Report
      2017 Research-status Report 2016 Research-status Report
  • [Patent(Industrial Property Rights)] 銀ナノ粒子樹脂複合体及び水素化触媒2019

    • Inventor(s)
      魚住泰広、大迫隆男
    • Industrial Property Rights Holder
      自然科学研究機構
    • Industrial Property Rights Type
      特許
    • Filing Date
      2019
    • Related Report
      2018 Annual Research Report
  • [Patent(Industrial Property Rights)] キラルロジウム錯体、及び光学活性β-置換カルボニル化合物の製造方法2018

    • Inventor(s)
      魚住泰広、大迫隆男、沈冠碩
    • Industrial Property Rights Holder
      大学共同利用機関法人 自然科学研究機構
    • Industrial Property Rights Type
      特許
    • Filing Date
      2018
    • Related Report
      2017 Research-status Report

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Published: 2016-04-21   Modified: 2020-03-30  

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