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Development and Application of Highly Chemoselective Organic Reductants

Research Project

Project/Area Number 19550108
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

KUROBOSHI Manabu  Okayama University, 大学院・自然科学研究科, 准教授 (30242316)

Project Period (FY) 2007 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2009: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2008: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2007: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Keywordsビオロゲン / 有機還元剤 / 電解還元 / ハロゲン化アリール / 還元的カップリング / ビアリール / イオン液体 / 水 / 有機電解 / 炭素-炭素結合形成 / パラジウム / カップリング反応 / Pd触媒 / 芳香族ハロゲン化物 / パラジウム触媒 / 還元的二量化
Research Abstract

Several viologen derivatives (1,1'-disubstituted 4,4'-bipyridynium, V^<2+>) were synthesized, and their electrochemical behavior was studied to reveal that 1) two one-electron reduction processes occurred on V2^+ to give V^<+・> and V^0, stepwise, and 2) V^0s worked as organic reductants compatible to zinc. V^0 were generated by electroreduction of V^<2+>, and promoted Pd-catalyzed reductive coupling of aryl halides to give the corresponding biaryls. By proper choice of substituents on N of V^<2+>, V^0 could be used in several media such as usual organic solvents, ionic liquids, and water. Moreover, electroreduction of N-substituted pyridinium derivatives also gave organic reductants.

Report

(4 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • 2007 Annual Research Report
  • Research Products

    (40 results)

All 2010 2009 2008 2007 Other

All Journal Article (10 results) (of which Peer Reviewed: 10 results) Presentation (29 results) Remarks (1 results)

  • [Journal Article] Design of redox-mediatory systems for electro-organic synthesis2009

    • Author(s)
      Tanaka, H. ; Kuroboshi, M. ; Mitsudo, K.
    • Journal Title

      Electrochemistry 77

      Pages: 1002-1009

    • NAID

      10025445931

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Development of aqueous media for electroorganic synthesis2009

    • Author(s)
      Tanaka, H. ; Kuroboshi, M.
    • Journal Title

      Kagaku to Kogyo 83

      Pages: 206-214

    • NAID

      40016664666

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Electroreductive generation of recyclable organic reductant from N, N'-dioctyl-4, 4'-bipyridinium and Pd-catalyzed reductive coupling of aryl halides2009

    • Author(s)
      Kuroboshi, M. ; Kobayashi, R. ; Nakagawa, T. ; Tanaka, H.
    • Journal Title

      Synlett

      Pages: 85-88

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Design of redox-mediatory systems for electro-organic synthesis2009

    • Author(s)
      Tanaka, H.; Kuroboshi, M.; Mitsudo, K.
    • Journal Title

      Electrochemistry 77

      Pages: 1002-1009

    • NAID

      10025445931

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of aqueous media for electroorganic synthesis2009

    • Author(s)
      Tanaka, H.; Kuroboshi, M
    • Journal Title

      Kagaku to Kogyo 83

      Pages: 206-214

    • NAID

      40016664666

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Electroreductive Generation of Recyclable Organic Reductant from N. N'-Dioctyl-4.4'-bipyridinium and Pd-Catalyzed Reductive Coupling of Aryl Hal ides2009

    • Author(s)
      Manabu KUROBOSHI
    • Journal Title

      Synlett

      Pages: 85-88

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Recyclable Electron Transfer System: Electroreduction of Viologen in Ionic Liquids and Pd-catalyzed Reductive Coupling of Aryl Halides2008

    • Author(s)
      Kuroboshi, M. ; Kuwano, A. ; Tanaka, H.
    • Journal Title

      Electrochemistry 76

      Pages: 862-864

    • NAID

      130002150774

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Electrooxidative Desulfurization/Chlorination. A Facile Synthesis of 4-Chloro-2-azetidinones, a Potent Intermediate for Carbapenems2008

    • Author(s)
      Manabu KUROBOSHI
    • Journal Title

      Heterocycles 76

      Pages: 1471-1484

    • NAID

      40016323243

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Recyclable Electron Transfer System : Electroreduction of Viologen in Ionic Liquids and Pd-catalyzed Reductive Coupling of Aryl Hal ides2008

    • Author(s)
      Manabu KUROBOSHI
    • Journal Title

      Electrochemistry 76

      Pages: 862-864

    • NAID

      130002150774

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Electroreductive generation of recyclable organic reductant from N, N'-dioctyl-4, 4'-bipyridinium and Pdcatalyzed reductive coupling of aryl halides

    • Author(s)
      Kuroboshi, M.; Kobayashi, R.; Nakagawa, T.; Tanaka, H.
    • Journal Title

      Synlett

      Pages: 85-88

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] 水中で機能する有機還元剤:両親媒性ビオロゲンの電解還元と炭素-炭素結合形成への展開2010

    • Author(s)
      田邉豪・山本貴嗣・黒星学・田中秀雄
    • Organizer
      日本化学会第90春季年会
    • Related Report
      2009 Final Research Report
  • [Presentation] 4-置換4級ピリジニウム塩の電気化学的挙動と有機還元剤としての応用2010

    • Author(s)
      鈴木亮祐・黒星学・田中秀雄
    • Organizer
      日本化学会第90春季年会
    • Related Report
      2009 Final Research Report
  • [Presentation] ビオロゲンの電解還元による有機還元剤の発生と反応。アリール/アリールカップリングへの展開2009

    • Author(s)
      黒星学・竹谷健太郎・鈴木亮祐・田中秀雄
    • Organizer
      日本化学会第89春季年会
    • Related Report
      2009 Final Research Report
  • [Presentation] 4-置換ピリジニウム塩の電気化学的挙動と有機還元剤への応用2009

    • Author(s)
      黒星学・鈴木亮祐・田中秀雄
    • Organizer
      電気化学会第76回大会
    • Related Report
      2009 Final Research Report
  • [Presentation] ビオロゲン誘導体の水中での電解還元による有機還元剤の調製と反応2009

    • Author(s)
      黒星学・山本貴嗣・青木隆之・田中秀雄
    • Organizer
      電気化学会第76回大会
    • Related Report
      2009 Final Research Report
  • [Presentation] 水中での電解還元による有機還元剤の調製と炭素-炭素結合形成への応用2009

    • Author(s)
      山本貴嗣・黒星学・田中秀雄
    • Organizer
      2009年電気化学秋季大会
    • Related Report
      2009 Final Research Report
  • [Presentation] 電解還元を利用する再利用可能な有機還元剤の調製とその利用2009

    • Author(s)
      黒星学・小林良人・桑野晶子・中川貴之・青木隆之・山本貴嗣・鈴木亮祐・田中秀雄
    • Organizer
      第33回有機電子移動化学討論会
    • Related Report
      2009 Final Research Report
  • [Presentation] 水中での電解還元による有機還元剤の調製と炭素-炭素結合形成への応用2009

    • Author(s)
      山本貴嗣・黒星学・田中秀雄
    • Organizer
      2009年電気化学秋季大会 1KO5(2009).
    • Place of Presentation
      東京農工大学小金井キャンパス
    • Related Report
      2009 Annual Research Report
  • [Presentation] 電解還元を利用する再利用可能な有機還元剤の調製とその利用2009

    • Author(s)
      黒星学・竹谷健太郎・鈴木亮祐・田中秀雄
    • Organizer
      第33回有機電子移動化学討論会 O-17(2009).
    • Place of Presentation
      慶応義塾大学
    • Related Report
      2009 Annual Research Report
  • [Presentation] ビオロゲンの電解還几による有機還几剤の発生と反応。アリール/アリールカップリングへの展開2009

    • Author(s)
      竹谷 健太郎
    • Organizer
      日本化学会第89春季年会(1F4-51)
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Related Report
      2008 Annual Research Report
  • [Presentation] 電解塩素化を活用する4-クロロー2-アゼチジノンの合成2009

    • Author(s)
      立山 翔一
    • Organizer
      日本化学会第89春季年会(3G4-11)
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Related Report
      2008 Annual Research Report
  • [Presentation] 活性炭に吸着した芳香族ハロゲン化物の電解還元脱ハロゲン化2009

    • Author(s)
      原 直彰
    • Organizer
      日本化学会第89春季年会(1F4-46)
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Related Report
      2008 Annual Research Report
  • [Presentation] ビオロゲン誘導体の水中での電解還元による有機還元剤の調製と反応2009

    • Author(s)
      山本 貴嗣
    • Organizer
      電気化学会第76回大会
    • Place of Presentation
      京都大学吉田キャンパス
    • Related Report
      2008 Annual Research Report
  • [Presentation] 4-置換ピリジニウム塩の電気化学的挙動と有機還元剤への応用2009

    • Author(s)
      鈴木 亮祐
    • Organizer
      電気化学会第76回大会
    • Place of Presentation
      京都大学吉田キャンパス
    • Related Report
      2008 Annual Research Report
  • [Presentation] 4-チオアゼチジノン誘導体の電解酸化一脱硫塩素化反応2009

    • Author(s)
      米田 昌弘
    • Organizer
      電気化学会第76回大会
    • Place of Presentation
      京都大学吉田キャンパス
    • Related Report
      2008 Annual Research Report
  • [Presentation] 還元型ビオロゲンを電子プールとする芳香族ハロゲン化物の水中二量化反応2008

    • Author(s)
      青木隆之・山本貴嗣・黒星学・田中秀雄
    • Organizer
      日本化学会第88春季年会
    • Related Report
      2009 Final Research Report
  • [Presentation] ビオロゲンを基本骨格とする有機還元剤の循環系の開発2008

    • Author(s)
      桑野晶子・鈴木亮祐・黒星学・田中秀雄
    • Organizer
      日本化学会第88春季年会
    • Related Report
      2009 Final Research Report
  • [Presentation] Pd/Viologen-Promoted Reductive Coupling of Aryl Halides in Aqueous Solution2008

    • Author(s)
      Kuroboshi, M. ; Aoki, T. ; Yamamoto, T. ; Tanaka, H.
    • Organizer
      213th ECS Meeting (Phoenix, Arizona), Abstr.
    • Related Report
      2009 Final Research Report
  • [Presentation] 水中で機能する有機還元剤の調製と芳香族ハロゲン化物の還元的カップリング反応2008

    • Author(s)
      山本貴嗣・青木隆之・黒星学・田中秀雄
    • Organizer
      第32回有機電子移動化学討論会
    • Related Report
      2009 Final Research Report
  • [Presentation] Recyclable Electron Transfer System: Viologen/Pd-Promoted Reductive Coupling of Aryl Halides in Ionic Liquid2008

    • Author(s)
      Kuroboshi, M. ; Kuwano, A. ; Tanaka, H.
    • Organizer
      214th ECS Meeting (Honolulu, Hawaii), Abstr.
    • Related Report
      2009 Final Research Report
  • [Presentation] Pd/Viologen-Promoted Reductive Coupling of Aryl Hal ides in Aqueous Solution2008

    • Author(s)
      Manabu KUEOBOSHI
    • Organizer
      213th ECS Meeting (535)
    • Place of Presentation
      Phoenix, AZ, USA
    • Related Report
      2008 Annual Research Report
  • [Presentation] Electroreductive Dehalogenation/Dimerization of Aryl Hal ides on an Activated Carbon Adsorbing Layer Using a Stacked-Type Cell2008

    • Author(s)
      Manabu KUROBOSHI
    • Organizer
      213th ECS Meeting (562)
    • Place of Presentation
      Phoenix, AZ, USA
    • Related Report
      2008 Annual Research Report
  • [Presentation] 水中で機能する有機還几剤の調製と芳香族ハロゲン化物の還冗的カップリング反応2008

    • Author(s)
      山本貴嗣
    • Organizer
      第32回有機電子移動化学討論会-エレクトロオーガニックケミストリー討論会 (P12)
    • Place of Presentation
      近畿大学本部キャンパス
    • Related Report
      2008 Annual Research Report
  • [Presentation] Recyclable Electron Transfer System : Viologen/Pd-Promoted Reductive Coupling of Aryl Hal ides in Ionic Liquid2008

    • Author(s)
      Manabu KUROBOSHI
    • Organizer
      214th ECS Meeting (1512)
    • Place of Presentation
      Honolulu, HI. USA
    • Related Report
      2008 Annual Research Report
  • [Presentation] 還元型ビオロゲンを電子プールとする芳香族ハロゲン化物の水中二量化反応2008

    • Author(s)
      青木 隆之
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      東京
    • Related Report
      2007 Annual Research Report
  • [Presentation] ビオロゲンを基本骨格とする有機還元剤の循環系の開発2008

    • Author(s)
      桑野 晶子
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      東京
    • Related Report
      2007 Annual Research Report
  • [Presentation] Mg2+ effects on electrochemical generation of reduced viologen (VO) and reactivity of VO2007

    • Author(s)
      田中秀雄
    • Organizer
      211th ECS Meeting
    • Place of Presentation
      米国・シカゴ
    • Related Report
      2007 Annual Research Report
  • [Presentation] 還元型ビオロゲン/遷移金属触媒を用いたハロゲン化アリールおよびアルケニルの還元的カップリング反応2007

    • Author(s)
      黒星 学
    • Organizer
      有機電子移動化学討論会
    • Place of Presentation
      鳥取
    • Related Report
      2007 Annual Research Report
  • [Presentation] ビオロゲン/Pd触媒を用いるハロゲン化アリールの電解還元二量化反応2007

    • Author(s)
      黒星 学
    • Organizer
      有機金属化学討論会
    • Place of Presentation
      広島
    • Related Report
      2007 Annual Research Report
  • [Remarks]

    • URL

      http://achem.okayama-u.ac.jp/eoc/index.html

    • Related Report
      2009 Final Research Report

URL: 

Published: 2007-04-01   Modified: 2016-04-21  

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