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Development of Introducing Method of Hetero-functional groups to Alkenes via Anti-Markovnikov Nucleophilic Attack as a Key Step

Research Project

Project/Area Number 23750112
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionNara Women's University

Principal Investigator

URA Yasuyuki  奈良女子大学, 自然科学系, 准教授 (40335196)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2012: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2011: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Keywordsパラジウム錯体 / ワッカー型酸化 / 逆マルコフニコフ求核攻撃 / 末端アルケン / ピナコール / キノン / 分子状酸素 / アルデヒド合成 / Wacker型酸化 / ビニルアレーン / アリールアセトアルデヒド / 酸化的開裂 / ベンズアルデヒド / 末端アセタール / 合成化学 / 有機化学 / 有機工業化学 / パラジウム錯体触媒
Research Abstract

We developed a synthetic method for terminal acetals from terminal alkenes and pinacol, and environmental load-reducing synthetic methods for aldehydes from terminal alkenes under mild reaction conditions. In these reactions, control of the regioselectivity of nucleophilic attack to coordinated alkenes is the key. By using bulky oxygen nucleophiles, the selectivity was successfully controlled to anti-Markovnikov manner.

Report

(3 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Research-status Report
  • Research Products

    (23 results)

All 2012 2011 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results) Presentation (19 results) Remarks (2 results)

  • [Journal Article] Palladium-catalyzed Synthesis of Terminal Acetals via Highly Selective Anti-Markovnikov Nucleophilic Attack of Pinacol on Vinylarenes, Allyl Ethers, and 1,5-Dienes2012

    • Author(s)
      Yamamoto, Mayumi; Nakaoka, Sonoe; Ura, Yasuyuki; Kataoka, Yasutaka
    • Journal Title

      Chemical Communications

      Volume: 48 Issue: 8 Pages: 1165-1167

    • DOI

      10.1039/c2cc16561a

    • NAID

      120006657547

    • URL

      http://hdl.handle.net/10935/3095

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Ruthenium-catalyzed Reduction of N-Alkoxy-and N-Hydroxyamides2011

    • Author(s)
      Fukuzawa, Hiroko; Ura, Yasuyuki; Kataoka, Yasutaka
    • Journal Title

      Journal of Organometallic Chemistry

      Volume: 696 Issue: 23 Pages: 3643-3648

    • DOI

      10.1016/j.jorganchem.2011.08.026

    • NAID

      120006657546

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] パラジウム触媒によるビニルアレーン類からの選択的なアリールアセトアルデヒド類の合成2012

    • Author(s)
      中岡園江,浦 康之,片岡靖隆
    • Organizer
      日本化学会第92 春季年会
    • Place of Presentation
      神奈川
    • Year and Date
      2012-03-25
    • Related Report
      2012 Final Research Report
  • [Presentation] SNS三座配位子を有するベンジルパラジウム錯体のプロトノリシス2012

    • Author(s)
      河田有未; 浦 康之; 片岡靖隆
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      神奈川
    • Related Report
      2011 Research-status Report
  • [Presentation] エナミドとアクリル酸エステルの酸化的環化によるルテナシクロペンタンの生成2012

    • Author(s)
      福沢紘子; 浦 康之; 片岡靖隆
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      神奈川
    • Related Report
      2011 Research-status Report
  • [Presentation] パラジウム触媒によるビニルアレーン類からの選択的なアリールアセトアルデヒド類の合成2012

    • Author(s)
      中岡園江; 浦 康之; 片岡靖隆
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      神奈川
    • Related Report
      2011 Research-status Report
  • [Presentation] インデン環がエチレン鎖で架橋されたNHC配位子を有するイリジウムI価カチオン錯体における分子内炭素-水素結合活性化反応2012

    • Author(s)
      橋本珠歩; 青山恭子; 浦 康之; 片岡靖隆
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      神奈川
    • Related Report
      2011 Research-status Report
  • [Presentation] η1: η1-型で配位したInd-P配位子を有するイリジウムIII価π-アリルカルボニル錯体の合成2012

    • Author(s)
      東中川朋恵; 浦 康之; 片岡靖隆
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      神奈川
    • Related Report
      2011 Research-status Report
  • [Presentation] Ruthenium-Catalyzed Highly Selective Codimerization and Cotrimerization of N-Vinylamides with Alkenes2011

    • Author(s)
      浦 康之; 辻田 寛; 福沢紘子; 松木伸悟; 片岡靖隆; 和田健司; 光藤武明; 近藤輝幸
    • Organizer
      Catalysis and Fine Chemicals 2011
    • Place of Presentation
      奈良
    • Related Report
      2011 Research-status Report
  • [Presentation] Diverse Syntheses of Alkenylsilane Deivatives Mediated by Iridium Complexes Bearing the Ind-P Ligand2011

    • Author(s)
      椿本 彩; 浦 康之; 片岡靖隆
    • Organizer
      Catalysis and Fine Chemicals 2011
    • Place of Presentation
      奈良
    • Related Report
      2011 Research-status Report
  • [Presentation] Synthesis of Iridium Complexes Coordinated with a Dialkylphosphinoethylindenyl Ligand Having a Phosphine-centered Chirality2011

    • Author(s)
      大鹿恭子; 浦 康之; 片岡靖隆
    • Organizer
      Catalysis and Fine Chemicals 2011
    • Place of Presentation
      奈良
    • Related Report
      2011 Research-status Report
  • [Presentation] Behavior and Reactivity of Cationic Pd(II) Complexes Having an SNS Ligand with N-Heterocycles at Terminals2011

    • Author(s)
      河田有未; 浦 康之; 片岡靖隆
    • Organizer
      Catalysis and Fine Chemicals 2011
    • Place of Presentation
      奈良
    • Related Report
      2011 Research-status Report
  • [Presentation] Preparation of Optically Active Ir(III) Complexes Having a Metal-Centered Chirality Available for Bifunctional Asymmetric Catalysis2011

    • Author(s)
      小寺 恵; 山本 緑; 浦 康之; 片岡靖隆
    • Organizer
      Catalysis and Fine Chemicals 2011
    • Place of Presentation
      奈良
    • Related Report
      2011 Research-status Report
  • [Presentation] Ruthenium-catalyzed Reduction of N-Alkoxy- and N-Hydroxyamides2011

    • Author(s)
      福沢紘子; 浦 康之; 片岡靖隆
    • Organizer
      Catalysis and Fine Chemicals 2011
    • Place of Presentation
      奈良
    • Related Report
      2011 Research-status Report
  • [Presentation] Behavior and Reactivity of Pd(II)-SNS Complexes Having N-Heterocycles at Terminals2011

    • Author(s)
      浦 康之; 河田有未; 片岡靖隆
    • Organizer
      第1回新学術領域「分子活性化」国際会議
    • Place of Presentation
      兵庫
    • Related Report
      2011 Research-status Report
  • [Presentation] 炭素-ケイ素結合形成・解裂を伴うイリジウムIII価シリルアルケニル錯体における金属上の不斉点の異性化反応2011

    • Author(s)
      椿本 彩; 浦 康之; 片岡靖隆
    • Organizer
      錯体化学会第61回討論会
    • Place of Presentation
      岡山
    • Related Report
      2011 Research-status Report
  • [Presentation] リン上に不斉点を有するホスフィノエチルインデニル配位子を利用したイリジウム錯体の合成2011

    • Author(s)
      大鹿恭子; 浦 康之; 片岡靖隆
    • Organizer
      錯体化学会第61回討論会
    • Place of Presentation
      岡山
    • Related Report
      2011 Research-status Report
  • [Presentation] イリジウムIII価シリルヒドリド錯体の金属上に発生する不斉点の安定性2011

    • Author(s)
      小寺 恵; 山本 緑; 浦 康之; 片岡靖隆
    • Organizer
      錯体化学会第61回討論会
    • Place of Presentation
      岡山
    • Related Report
      2011 Research-status Report
  • [Presentation] Ind-P配位子を有するイリジウム錯体を用いた末端アルキンの立体選択的ヒドロシリル化反応2011

    • Author(s)
      椿本 彩; 浦 康之; 片岡靖隆
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      愛知
    • Related Report
      2011 Research-status Report
  • [Presentation] 両端にN-ヘテロ環を導入したSNS三座配位子を有する二価パラジウム錯体の合成、挙動および反応性2011

    • Author(s)
      河田有未; 浦 康之; 片岡靖隆
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      愛知
    • Related Report
      2011 Research-status Report
  • [Presentation] Ruthenium-Catalyzed Highly Selective Codimerization and Cotrimerization of Alkenes2011

    • Author(s)
      浦 康之
    • Organizer
      第14回アジア化学会議(招待講演)
    • Place of Presentation
      タイ
    • Related Report
      2011 Research-status Report
  • [Remarks]

    • URL

      http://www.chem.nara-wu.ac.jp/~kataoka/index.html

    • Related Report
      2012 Final Research Report
  • [Remarks]

    • URL

      http://www.chem.nara-wu.ac.jp/~kataoka/research-Ura.html

    • Related Report
      2011 Research-status Report

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

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