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Development of highly atom-efficient addition reactions with catalytic functionalizations

Research Project

Project/Area Number 24245021
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionKyoto University

Principal Investigator

TSUJI Yasushi  京都大学, 工学(系)研究科(研究院), 教授 (30144330)

Co-Investigator(Renkei-kenkyūsha) FUJIHARA Tetsuaki  京都大学, 大学院工学研究科, 助教 (30374698)
Project Period (FY) 2012-05-31 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥37,570,000 (Direct Cost: ¥28,900,000、Indirect Cost: ¥8,670,000)
Fiscal Year 2014: ¥10,660,000 (Direct Cost: ¥8,200,000、Indirect Cost: ¥2,460,000)
Fiscal Year 2013: ¥12,220,000 (Direct Cost: ¥9,400,000、Indirect Cost: ¥2,820,000)
Fiscal Year 2012: ¥14,690,000 (Direct Cost: ¥11,300,000、Indirect Cost: ¥3,390,000)
Keywordsカルボニル化合物 / 遷移金属触媒 / 官能基化 / パラジウム触媒 / 銅触媒 / 高選択的反応 / カルボニル基 / 付加反応 / イリジウム触媒 / 酸塩化物 / 高選択的 / アルキン / 脱カルボニル化反応 / 立体選択的 / 位置選択的
Outline of Final Research Achievements

Highly selective and efficient functionalizations of unsaturated substrates such as alkynes and 1,2-dienes (allenes) have been developed by utilizing acid chlorides, aldehydes, formamides, and carbon dioxides as functionality sources. Unlike former transformations, proper choice of central metals and ligands of the catalyst prevent loss of the functionalities during the catalytic reactions. Further addition of hydrosilanes, silylboranes, and diboranes to the catalytic systems realized reductive, silylative, and borylative functionalizations.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • Research Products

    (24 results)

All 2014 2013 2012 Other

All Journal Article (10 results) (of which Peer Reviewed: 10 results,  Acknowledgement Compliant: 5 results) Presentation (13 results) (of which Invited: 9 results) Remarks (1 results)

  • [Journal Article] Copper-Catalyzed Regiodivergent Silacarboxylation of Allenes with Carbon Dioxide and a Silylborane2014

    • Author(s)
      Tani, Yosuke; Fujihara, Tetsuaki; Terao, Jun; Tsuji, Yasushi
    • Journal Title

      Journal of the American Chemical Society

      Volume: 136 Issue: 51 Pages: 17706-17709

    • DOI

      10.1021/ja512040c

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Copper-Catalyzed Borylative AllylAllyl Coupling Reaction2014

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

      Angew. Chem. Int. Ed

      Volume: 53 Issue: 34 Pages: 9007-9011

    • DOI

      10.1002/anie.201404173

    • NAID

      120005649312

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Palladium-Catalyzed Formal Arylacylation of Allenes Employing Acid Chlorides and Arylboronic Acids2014

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

      Chem. Commun.,

      Volume: 50 Issue: 62 Pages: 8476-8479

    • DOI

      10.1039/c4cc03173c

    • NAID

      120005661569

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Transiton Metal-Catalyzed Synthesis of π-Conjugated Cyclic Esters and Amides from Alkynes and Carbonyl Reagents2014

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

      Heterocycles

      Volume: 89 Issue: 6 Pages: 1343-1367

    • DOI

      10.3987/rev-13-786

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Iron Oxide Catalyzed Reduction of Acid Chlorides to Aldehydes with Hydrosilanes2014

    • Author(s)
      C. Cong, T. Fujihara,J. Terao, Y. Tsuji
    • Journal Title

      Catal. Commun

      Volume: 50 Pages: 25-28

    • DOI

      10.1016/j.catcom.2014.02.018

    • NAID

      120005466662

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Palladium-Catalyzed Formal Hydroacylation of Allenes Employing Acid Chlorides and Hydrosilanes2013

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

      Org. Lett.,

      Volume: 15 Issue: 9 Pages: 2286-2289

    • DOI

      10.1021/ol400862k

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Borylation of alpha-Alkoxyallenes with Bis(pinacolato)diboron: Efficient Synthesis of 2-Boryl-1,3-butadienes2013

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

      Angew. Chem. Int. Ed

      Volume: 52 Issue: 47 Pages: 12400-12403

    • DOI

      10.1002/anie.201306843

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iridium-Catalyzed Addition of Aroyl Chlorides and Aliphatic Acid Chlorides to Terminal Alkynes2012

    • Author(s)
      Iwai, T. ; Fujihara, T. ; Terao, J. ; Tsuji, Y.
    • Journal Title

      J.Am.Chem.Soc.

      Volume: 134 Issue: 2 Pages: 1268-1274

    • DOI

      10.1021/ja209679c

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Esterification of Aryl Halides Using Aryl Formates without the Use of External Carbon Monoxide2012

    • Author(s)
      T. Fujihara, T. Hosoki, Y. Katafuchi, T. Iwai, J. Terao, Y. Tsuji
    • Journal Title

      Chem. Commun.

      Volume: 48 Issue: 64 Pages: 8012-8014

    • DOI

      10.1039/c2cc33944g

    • NAID

      120005298241

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Reduction of Acid Chlorides to Aldehydes with Hydrosilanes2012

    • Author(s)
      Tetsuaki Fujihara
    • Journal Title

      Synlett

      Volume: 23 Issue: 16 Pages: 2389-2392

    • DOI

      10.1055/s-0032-1317155

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Presentation] 均一系遷移金属触媒を用いる不飽和化合物の選択的官能基化反応2014

    • Author(s)
      辻 康之
    • Organizer
      平成26年度触媒学会西日本支部触媒技術セミナー
    • Place of Presentation
      京都
    • Year and Date
      2014-11-14
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Transition-metal-catalyzed Carboxylation using Carbon Dioxide2014

    • Author(s)
      Yasushi Tsuji
    • Organizer
      Vietnam Malaysia International Chemical Congress
    • Place of Presentation
      Hanoi, Vietnam
    • Year and Date
      2014-11-07
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Transition-metal-catalyzed Functionalization using Carbonyl Compounds2014

    • Author(s)
      Yasushi Tsuji
    • Organizer
      18th Malaysian International Chemical Congress
    • Place of Presentation
      Kuala Lumpur, Malaysia
    • Year and Date
      2014-11-03
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 非貴金属遷移金属触媒を用いる高効率官能基化反応の開発2014

    • Author(s)
      辻 康之
    • Organizer
      有機合成化学を起点とするものづくり戦略第3回ミニシンポジウム
    • Place of Presentation
      京都
    • Year and Date
      2014-09-29
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Addition of Carbonyl Functionalities to Carbon–Carbon Multiple Bonds Catalyzed by a Transition-metal Complex2014

    • Author(s)
      Yasushi Tsuji
    • Organizer
      Universitat Autònoma de Barcelon, Special Lecture
    • Place of Presentation
      Barcelona, Spain
    • Year and Date
      2014-04-22
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] パラジウム触媒を用いる酸塩化物とアリールボロン酸によるアレンのアリールアシル化反応2014

    • Author(s)
      野木 馨介・藤原 哲晶・寺尾 潤・辻 康之
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋(名古屋大学)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 酸化鉄触媒存在下ヒドロシランを用いた酸塩化物からのアルデヒド合成2014

    • Author(s)
      叢 聡・藤原 哲晶・寺尾 潤・辻 康之
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋(名古屋大学)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Transition-metal Catalyzed Addition of Carbonyl Functionalities to Unsaturated Compounds2013

    • Author(s)
      Yasushi Tsuji
    • Organizer
      ACP Lectureship in Taiwan
    • Place of Presentation
      National Taiwan Normal University
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Long-range Steric Effect in Homogeneous Nanosize Catalysis2012

    • Author(s)
      Yasushi Tsuji
    • Organizer
      1st International Conference on Emerging Advanced Nanomaterials
    • Place of Presentation
      Brisbane, Australia
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Transition-metal Catalyzed Carboxylation Employing Carbon Dioxide2012

    • Author(s)
      Yasushi Tsuji
    • Organizer
      The 7th International Conference on Cutting-edge Organic Chemistry in Asia
    • Place of Presentation
      Nanyang Technological University, Singapore
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] 触媒的官能基付加を基軸とする高効率変換反応の開発2012

    • Author(s)
      辻 康之
    • Organizer
      第44回有機合成セミナー「新製品創出のための有機合成」
    • Place of Presentation
      大阪市立工業研究所,大阪
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Palladium-catalyzed Hydroacylation of Allenes Employing Acid Chlorides and Hydrosilanes2012

    • Author(s)
      Kenta Tatsumi
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-12)
    • Place of Presentation
      Kyoto (Japan)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 銅触媒存在下ヒドロシランを還元剤としたカルボン酸からのアルデヒド合成2012

    • Author(s)
      叢 聡
    • Organizer
      石油学会関西支部 第21回研究発表会
    • Place of Presentation
      大阪(大阪大学中之島センター)
    • Related Report
      2012 Annual Research Report
  • [Remarks] 辻 研究室 ホームページ

    • URL

      http://twww.ehcc.kyoto-u.ac.jp/

    • Related Report
      2014 Annual Research Report

URL: 

Published: 2012-11-27   Modified: 2019-07-29  

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