• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Development of Highly Efficient Fictionalization of Unsaturated Hydrocarbons

Research Project

Project/Area Number 17H03096
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Green/Environmental chemistry
Research InstitutionKyoto University

Principal Investigator

Tsuji Yasushi  京都大学, 工学研究科, 名誉教授 (30144330)

Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥14,300,000 (Direct Cost: ¥11,000,000、Indirect Cost: ¥3,300,000)
Fiscal Year 2019: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2018: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000)
Fiscal Year 2017: ¥6,370,000 (Direct Cost: ¥4,900,000、Indirect Cost: ¥1,470,000)
Keywords不飽和炭化水素 / 1,2-ジエン / 1,3-ジエン / 銅 / ジボロン / シリルボラン / シラアシル化反応 / ニトリル / ホウ素 / ケイ素 / アレン / 銅触媒 / ホウ素化反応 / アシル化反応 / グリーンケミストリ / ジボラン / 二酸化炭素 / シリル化 / ホウ素化
Outline of Final Research Achievements

In this research project, we performed copper-catalyzed borylative and silylative transformations of carbon-carbon unsaturated compounds using boryl copper and silyl copper intermediates. As a result, we successfully developed several copper-catalyzed reactions such as boraformylation and silaformylation of 1,2-dienes, bora-acylation of 1,2-dienes, [4+2]cycloaddition of 2-pyridylketimines and alkynes, and three-component coupling of nitriles, 1,3-dienes and silylboranes.

Academic Significance and Societal Importance of the Research Achievements

本申請課題での学術的意義は,銅を触媒とする不飽和化合物の効率的官能基化反応の開発に成功した点にある.銅触媒による有機合成反応の開発は,金属に結合する配位子によって制御されることは知られているが,本研究で見出した新しい有機合成反応においても,適切な配位子を用いることにより,効率や選択性が大きく向上することを明らかにした.

Report

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

    (28 results)

All 2020 2019 2018 2017

All Journal Article (15 results) (of which Peer Reviewed: 15 results,  Open Access: 5 results,  Acknowledgement Compliant: 1 results) Presentation (13 results) (of which Int'l Joint Research: 5 results,  Invited: 4 results)

  • [Journal Article] Cu-Catalyzed Three-Component Coupling Reactions Using Nitriles, 1,3-Dienes and Silylboranes2020

    • Author(s)
      Y. Matsuda, Y. Tsuji, T. Fujihara
    • Journal Title

      Chem.Commun.

      Volume: 56 Issue: 34 Pages: 4648-4651

    • DOI

      10.1039/d0cc01803a

    • NAID

      120006954063

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pd-Catalyzed Synthesis of Fluorenes via Intramolecular C(sp2)-H Activation at Room Temperature2020

    • Author(s)
      Y. Tanji, Y. Tsuji, T. Fujihara
    • Journal Title

      Synlett

      Volume: 31 Issue: 08 Pages: 805-808

    • DOI

      10.1055/s-0039-1690812

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pyridines Bearing Poly(ethylene glycol) Chains: Synthesis and Use as Ligands2020

    • Author(s)
      M. Satou, A, Kiyooka, Y. Tsuji, T. Fujihara
    • Journal Title

      Asian J. Org. Chem.

      Volume: 8 Issue: 5 Pages: 761-764

    • DOI

      10.1002/ajoc.202000062

    • NAID

      120006954064

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pd-catalyzed Intermolecular C-H bond Arylation Reactions: Effect of Bulkiness of Carboxylate Ligands2020

    • Author(s)
      Y. Tanji, R. Hamaguchi, Y. Tsuji, T. Fujihara
    • Journal Title

      Chem. Commun.

      Volume: 56 Issue: 27 Pages: 3843-3846

    • DOI

      10.1039/d0cc01129k

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Zinc-Catalyzed Synthesis of Acylsilanes Using Carboxylic Acids and a Silylborane in the Presence of Pivalic Anhydride2019

    • Author(s)
      K. Tatsumi, S. Tanabe, Y. Tsuji, T. Fujihara
    • Journal Title

      Org. Lett.

      Volume: 21 Issue: 24 Pages: 10130-10133

    • DOI

      10.1021/acs.orglett.9b04151

    • NAID

      120006954065

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Bora-acylation and Bora-alkoxyoxalylation of Allenes2018

    • Author(s)
      A. Sawada, T. Fujihara, Y. Tsuji
    • Journal Title

      Adv. Synth. Catal.

      Volume: 360 Issue: 14 Pages: 2621-2625

    • DOI

      10.1002/adsc.201800311

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed [4+2] Cycloaddition Using N-(2-pyridyl)Ketimines and Terminal Alkynes2018

    • Author(s)
      K. Tatsumi, T. Fujihara, J. Terao, Y. Tsuji
    • Journal Title

      Adv. Synth. Catal.

      Volume: 360 Issue: 17 Pages: 3245-3248

    • DOI

      10.1002/adsc.201800704

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cobalt-Catalyzed Reductive Coupling of Alkynes and Acrylates Bearing a Leaving Group: Construction of Cyclobutene Rings2018

    • Author(s)
      T. Fujihara, S. Kukita, Y. Yagi, M. Kirihara, K. Nogi, Y. Tsuji
    • Journal Title

      Asian J. Org. Chem.

      Volume: 7 Issue: 12 Pages: 2456-2458

    • DOI

      10.1002/ajoc.201800561

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cu-catalyzed Borylative and Silylative Transformations of Allenes: Use of beta-Functionalized Allyl Copper Intermediates in Organic Synthesis2018

    • Author(s)
      T. Fujihara, Y. Tsuji
    • Journal Title

      Synthesis

      Volume: 50 Issue: 09 Pages: 1737-1749

    • DOI

      10.1055/s-0036-1591777

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cu-catalyzed Transformations of Allenes: Use of in-situ Generated Allyl Copper Intermediates in Organic Synthesis2018

    • Author(s)
      藤原哲晶、 辻 康之
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 76 Issue: 4 Pages: 336-345

    • DOI

      10.5059/yukigoseikyokaishi.76.336

    • NAID

      130006646868

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Boraformylation and Silaformylation of Allenes2017

    • Author(s)
      T. Fujihara, A. Sawada, T. Yamaguchi, Y. Tani, J. Terao, Y. Tsuji
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 56 Issue: 6 Pages: 1539-1543

    • DOI

      10.1002/anie.201611314

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Copper-Catalyzed Hydroallylation of Allenes Employing Hydrosilanes and Allyl Chlorides2017

    • Author(s)
      T. Fujihara, K. Yokota, J. Terao, Y. Tsuji
    • Journal Title

      Chem. Commun

      Volume: 53 Issue: 56 Pages: 7898-7900

    • DOI

      10.1039/c7cc02816d

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of a Dinuclear Copper NHC Complex Bearing a Rigid π-Conjugated Cyclic Framework2017

    • Author(s)
      D. Inamori. T. Miwa, T. Fujihara, Y. Tsuji, J. Terao
    • Journal Title

      Synlett

      Volume: 28 Issue: 14 Pages: 1775-1779

    • DOI

      10.1055/s-0036-1588824

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Hetero Face-to-Face Porphyrin Array with the Cooperative Effects of Coordination and Host-Guest Complexation2017

    • Author(s)
      Y. Chiba. M. Liu, Y. Tachibana, T. Fujihara, Y. Tsuji, J. Terao
    • Journal Title

      Chem. Asian J

      Volume: 12 Issue: 15 Pages: 1900-1904

    • DOI

      10.1002/asia.201700738

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Programmed Synthesis of Molecular Wires with Fixed Insulation and Defined Length Based on Oligo(phenylene ethynylene) and Permethylated α-Cyclodextrins2017

    • Author(s)
      Masai Hiroshi、Fujihara Tetsuaki、Tsuji Yasushi、Terao Jun
    • Journal Title

      Chemistry - A European Journal

      Volume: 23 Issue: 60 Pages: 15073-15079

    • DOI

      10.1002/chem.201701428

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Presentation] 亜鉛触媒によるカルボン酸とシリルボランを用いたアシルシラン合成法の開発2019

    • Author(s)
      田邉沙絵、巽 謙太、辻 康之、藤原哲晶
    • Organizer
      有機合成若手セミナー
    • Related Report
      2019 Annual Research Report
  • [Presentation] 銅触媒を用いたシリル基導入を伴う1,3-ジエンの位置選択的二官能基化反応2019

    • Author(s)
      金山和貴、松田佑樹、辻康之、藤原哲晶
    • Organizer
      第66回有機金属化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 銅触媒による1,3-ジエンとジボロンを用いた環状アリルボレート合成2019

    • Author(s)
      秋葉智文,棚橋拓海,辻康之,藤原哲晶
    • Organizer
      日本化学会第9回CSJフェスタ
    • Related Report
      2019 Annual Research Report
  • [Presentation] パラジウム触媒による分子間炭素-水素結合アリール化反応におけるカルボキシラート配位子の立体効果2019

    • Author(s)
      濱口稜,丹治優,辻康之,藤原哲晶
    • Organizer
      日本化学会第9回CSJフェスタ
    • Related Report
      2019 Annual Research Report
  • [Presentation] Steric Effect of Bulky Carboxylate Ligands on Pd-Catalyzed Intramolecular C-H Bond Arylation Reactions2019

    • Author(s)
      Y. Tanji, T. Fujihara, Y. Tsuji
    • Organizer
      20th Organometallic Catalysis Directed Towards Organic Synthesis
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] コバルト触媒による二酸化炭素捕捉過程を含む多成分連結反応の開発2018

    • Author(s)
      藤原哲晶,野木馨介,久木田進,辻康之
    • Organizer
      第113回有機合成シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] Cobalt-Catalyzed Carboxyzincation of Alkynes Using Carbon Dioxide and Zinc Powder2018

    • Author(s)
      T. Fujihara, K. Nogi, Y. Tsuji
    • Organizer
      International Conference on Coordination Chemistry, 2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Copper-Catalyzed Borylative and Silylative Transformation of Allenes2018

    • Author(s)
      T. Fujihara, A. Sawada, T. Yamaguchi, Y. Tsuji
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry
    • Related Report
      2018 Annual Research Report
  • [Presentation] Bulky Carboxylate-Assisted Room Temperature Pd-Catalyzed Intramolecular C-H Bond Arylation Reactions2018

    • Author(s)
      Y. Tanji, T. Fujihara, Y. Tsuji
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry
    • Related Report
      2018 Annual Research Report
  • [Presentation] 銅触媒を用いた1,3-ジエンの位置選択的ボラホルミル化反応およびシラホルミル化反応2018

    • Author(s)
      金山和貴,沢田あゆみ,藤原哲晶,辻康之
    • Organizer
      第27回石油学会関西支部研究発表会
    • Related Report
      2018 Annual Research Report
  • [Presentation] (3)Transition-metal-catalyzed functionalization using carbon dioxide2017

    • Author(s)
      Yasushi Tsuji
    • Organizer
      The 253rd ACS National Meeting
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Catalytic Carboxylation using Carbon Dioxide2017

    • Author(s)
      Yasushi Tsuji
    • Organizer
      Kyoto University International Symposium: Nordic/Kyoto OMCOS 2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Catalytic Functionalization of Unsaturated Compounds2017

    • Author(s)
      Yasushi Tsuji
    • Organizer
      The 46th World Chemistry Congress of the International Union of Pure and Applied Chemistry (IUPAC-2017)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited

URL: 

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

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi