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Development of environmental load-reducing oxidation reactions involving anti-Markovnikov nucleophilic attack to alkenes as a key step

Research Project

Project/Area Number 25410116
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
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) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords環境低負荷型酸化反応 / アルケン / 逆マルコフニコフ求核攻撃 / アルデヒド合成 / パラジウム触媒 / 分子状酸素 / 末端アセタール合成 / 酸化的開裂 / 環境低負荷型反応 / パラジウム錯体触媒 / ビニルアレーン / 逆マルコフニコフ選択性 / アセタール合成 / パラジウム / Wacker型酸化反応 / アリールアセトアルデヒド / 末端アセタール / ベンズアルデヒド誘導体 / 逆マルコフニコフ型求核攻撃
Outline of Final Research Achievements

We have developed three types of oxidation reactions, i.e., (1) synthesis of arylacetaldehydes via anti-Markovnikov Wacker-type oxidation, (2) synthesis of terminal acetals, (3) synthesis of benzaldehydes via oxidative cleavage of carbon-carbon double bond, using palladium catalysts and vinylarenes as substrates. These reactions proceeded under 1 atm of molecular oxygen (as a terminal oxidant) and mild reaction conditions, and thus these can be regarded as novel environmental load-reducing synthesis of aldehydes and their derivatives from terminal alkenes. The use of cyclic electron-deficient alkenes such as maleimide as additives was the key of the present reactions to enhance the catalytic activity.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (17 results)

All 2016 2015 2014 2013

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 1 results) Presentation (14 results) (of which Invited: 1 results)

  • [Journal Article] Maleimide-assisted Anti-Markovnikov Wacker-type Oxidation of Vinylarenes Using Molecular Oxygen as a Terminal Oxidant2016

    • Author(s)
      Nakaoka, Sonoe; Murakami, Yuka; Kataoka, Yasutaka; Ura, Yasuyuki
    • Journal Title

      Chemical Communications

      Volume: 52 Issue: 2 Pages: 335-338

    • DOI

      10.1039/c5cc06746d

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Tiara-like Octanuclear Palladium(II) and Platinum(II) Thiolates and Their Inclusion Complexes with Dihalo- or Iodoalkanes2014

    • Author(s)
      Yamashina, Yukari; Kataoka, Yasutaka; Ura, Yasuyuki*
    • Journal Title

      Inorganic Chemistry

      Volume: 53 Issue: 7 Pages: 3558-3567

    • DOI

      10.1021/ic403050c

    • NAID

      120006657812

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Fluxional Interconversion of Divalent Palladium Complexes Having NSNSN Ligands between Flexible SNS and Rigid NNN-Coordinated Structures2013

    • Author(s)
      Kawada, Yumi; Kataoka, Yasutaka; Ura, Yasuyuki*
    • Journal Title

      Dalton Transactions

      Volume: 42 Issue: 41 Pages: 14844-14855

    • DOI

      10.1039/c3dt51592c

    • NAID

      120006657780

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 分子状酸素を用いたパラジウム/銅触媒によるビニルアレーンからのベンズアルデヒド誘導体の合成2016

    • Author(s)
      村上祐香; 中岡園江; 浦 康之; 片岡靖隆
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      京都,同志社大学
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 分子状酸素を末端酸化剤として用いたパラジウム触媒によるビニルアレーンの逆マルコフニコフ型酸化反応2015

    • Author(s)
      村上祐香; 中岡園江; 浦 康之; 片岡靖隆
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      大阪,関西大学
    • Year and Date
      2015-09-07
    • Related Report
      2015 Annual Research Report
  • [Presentation] SNS型配位子を有するベンジルパラジウム錯体の酸素に対する反応性2015

    • Author(s)
      下川礼奈; 河田有未; 浦 康之; 片岡靖隆
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      千葉県船橋市
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] ベンジルパラジウム錯体と酸素との反応における塩化物イオン源の加速効果2014

    • Author(s)
      下川礼奈; 河田有未; 浦 康之; 片岡靖隆
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      福岡県福岡市
    • Year and Date
      2014-09-25
    • Related Report
      2014 Research-status Report
  • [Presentation] Effect of the Addition of Chloride Ion Sources on the Reaction of an SNS-Benzylpalladium Complex toward O22014

    • Author(s)
      下川礼奈; 河田有未; 浦 康之; 片岡靖隆
    • Organizer
      XXVI International Conference on Organometallic Chemistry (ICOMC2014)
    • Place of Presentation
      北海道札幌市
    • Year and Date
      2014-07-16
    • Related Report
      2014 Research-status Report
  • [Presentation] パラジウム8核ティアラ型錯体[Pd(μ-SCH2CO2Me)2]8と10族遷移金属錯体との反応2014

    • Author(s)
      山科友香理; 浦 康之; 片岡靖隆
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      愛知
    • Related Report
      2013 Research-status Report
  • [Presentation] ヨウ素分子を包接したパラジウム8核ティアラ型錯体[Pd(μ-SCH2CO2Me)2]8の構造,挙動および反応性2013

    • Author(s)
      山科友香理; 浦 康之; 片岡靖隆
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
  • [Presentation] SNS型三座配位子を有するベンジルパラジウム錯体と分子状酸素との反応における塩化物イオンの添加効果2013

    • Author(s)
      下川礼奈; 河田有未; 浦 康之; 片岡靖隆
    • Organizer
      錯体化学会第63回討論会
    • Place of Presentation
      沖縄
    • Related Report
      2013 Research-status Report
  • [Presentation] 小分子を包接したパラジウム8核ティアラ型錯体[Pd(μ-SCH2CO2Me)2]8の挙動と反応性2013

    • Author(s)
      山科友香理; 浦 康之; 片岡靖隆
    • Organizer
      錯体化学会第63回討論会
    • Place of Presentation
      沖縄
    • Related Report
      2013 Research-status Report
  • [Presentation] Effect of the Addition of Chloride Ion on the Reaction of an SNS-Benzylpalladium Complex with O22013

    • Author(s)
      下川礼奈; 河田有未; 浦 康之; 片岡靖隆
    • Organizer
      第2回日仏錯体化学シンポジウム2013
    • Place of Presentation
      奈良
    • Related Report
      2013 Research-status Report
  • [Presentation] An Octanuclear Palladium Tiara-like Complex Including I22013

    • Author(s)
      山科友香理; 浦 康之; 片岡靖隆
    • Organizer
      第2回日仏錯体化学シンポジウム2013
    • Place of Presentation
      奈良
    • Related Report
      2013 Research-status Report
  • [Presentation] Binuclear Palladium Complexes Having Bis(bipyridyl)ferrocene2013

    • Author(s)
      藤野佐紀; 浦 康之; 片岡靖隆
    • Organizer
      第2回日仏錯体化学シンポジウム2013
    • Place of Presentation
      奈良
    • Related Report
      2013 Research-status Report
  • [Presentation] A Tiara-like Octanuclear Palladium Thiolate Complex Including Iodine Molecule2013

    • Author(s)
      浦 康之
    • Organizer
      International Symposium on Frontiers of Organometallic Chemistry (Post Symposium of C&FC 2013)
    • Place of Presentation
      中国
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] Reactivity of SNS-Benzylpalladium Complexes toward O2: HCl-accelerated Selective Formation of Benzyl Hydroperoxide2013

    • Author(s)
      浦 康之; 下川礼奈; 河田有未; 片岡靖隆
    • Organizer
      ファインケミカルズ合成触媒国際会議2013 (C&FC 2013)
    • Place of Presentation
      中国
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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