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Electrochemically generated trifluoromethyl cation equivalent

Research Project

Project/Area Number 23655085
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionOkayama University

Principal Investigator

SUGA Seiji  岡山大学, 大学院・自然科学研究科, 教授 (50291430)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2011: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsトリフルオロメチル基 / トリフルオロ酢酸 / 電気化学 / 電解酸化 / マイクロリアクター / 酸化電位 / 電子移動 / カチオン / マイクロ化学 / クラウンエーテル
Research Abstract

Generation of trifluoromethyl cation equivalents via electrochemical oxidation of trifluoroacetic acid was examined. Although we have not get trifluoromethyl cation equivalents in hand、some important information concerning oxidation of trifluoroacetic acid was obtained. Oxidation potential of trifluoroacetic acid was decreased by ether additives. Electrochemical microflow reactors are potential tools to effectively oxidize trifluoroacetic acid for the trifluoromethylation.

Report

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

    (31 results)

All 2013 2012 2011 Other

All Journal Article (11 results) (of which Peer Reviewed: 11 results) Presentation (16 results) (of which Invited: 4 results) Remarks (1 results) Patent(Industrial Property Rights) (3 results)

  • [Journal Article] Addition of ArSSAr to Alkenes. Implication of a Cationic Chain Mechanism Initiated by Electrogenerated ArS(ArSSAr)+2013

    • Author(s)
      Matsumoto, K.; Sanada, T.; Shimazaki, H.; Shimada, K.; Hagiwara, S.; Fujie, S.; Ashikari, Y.; Suga, S.; Kashimura, S.; Yoshida, J.
    • Journal Title

      Asian J. Org. Chem.

      Volume: 2 Issue: 4 Pages: 325-329

    • DOI

      10.1002/ajoc.201300017

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article]2013

    • Author(s)
      Mitsudo、K.; Harada、J.; Tanaka、Y.; Mandai、H.; Nishioka、Tanaka、H.; Wakamiya、A.; Murata、Y.; Suga、S.
    • Journal Title

      J. Org. Chem

      Volume: 78 Issue: 6 Pages: 2763-8

    • DOI

      10.1021/jo302652r

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Electro-reductive cyclization of aryl halides promoted by fluorene derivatives2012

    • Author(s)
      Koichi Mitsudo
    • Journal Title

      Electrochimica Acta

      Volume: 82 Pages: 444-449

    • DOI

      10.1016/j.electacta.2012.03.130

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Site-selective sequential coupling reactions controlled by “ Electrochemical Reaction Site Switching”:a straightforward approach to 1,4-bis(diaryl)buta-1,3-diynes2012

    • Author(s)
      Mitsudo, K.; Kamimoto, N.; Murakami, H.; Mandai, H.; Wakamiya, A.; Murata, Y.; Suga, S.
    • Journal Title

      Org. Biomol. Chem.

      Volume: 10 Issue: 48 Pages: 9562-9569

    • DOI

      10.1039/c2ob26567b

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Electrophilic substitution reactions using an electrogenerated ArS(ArSSAr)+ cation pool as an ArS+ equivalent2012

    • Author(s)
      Matsumoto, K; Kozuki, Y; Ashikari, Y; Suga, S; Kashimura, S; Yoshida, J
    • Journal Title

      Tetrahedron Lett.

      Volume: 53 Issue: 15 Pages: 1916-1919

    • DOI

      10.1016/j.tetlet.2012.01.131

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Nitrogen-Bridged Terthiophenes by Tandem Buchwald-Hartwig Coupling and Their Properties2012

    • Author(s)
      Mitsudo, K.; Shimohara, S.; Mizoguchi, J.; Mandai, H.; Suga, S.
    • Journal Title

      Org. Lett.

      Volume: 14 Issue: 11 Pages: 2702-2705

    • DOI

      10.1021/ol300887t

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Studies on the Petasis Reaction of 2-Pyridinecarbaldehyde Derivatives and Its Products2012

    • Author(s)
      Mandai,H.; Murota, K.; Suga, S.
    • Journal Title

      Heterocycles

      Volume: 85 Issue: 7 Pages: 1655-1669

    • DOI

      10.3987/com-12-12500

    • NAID

      40019365238

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Kinetic Resolution of Secondary Alcohols by the Combination of a Chiral Bronsted Acid, DABCO, and Acetyl Chloride2012

    • Author(s)
      Mandai,H.; Murota, K.; Mitsudo, K.; Suga, S.
    • Journal Title

      Org. Lett.

      Volume: 14 Issue: 13 Pages: 3486-3489

    • DOI

      10.1021/ol301373x

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Organic reactions mediated by electrochemically generated ArS+2011

    • Author(s)
      K. Matsumoto, S. Suga, J. Yoshida
    • Journal Title

      Org. Biomol. Chem.

      Volume: 9 Pages: 2586-2596

    • NAID

      120004205175

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthetic Studies of DMAP Derivatives by Diastereoselective Ugi Reaction2011

    • Author(s)
      Mandai, H.; Irie, S.; Mitsudo, K.; Suga, S.
    • Journal Title

      Molecules

      Volume: 16 Pages: 8815-8832

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] 7)Kumada-Tamao-Corriu Coupling Using N-Heterocyclic Carbene Ligands Bearing Pyridyl Group and Ethylenedioxyl Moiety.2011

    • Author(s)
      K. Mitsudo, Y. Doi, S. Sakamoto, H. Murakami, H. Mandai, S. Suga
    • Journal Title

      Chem. Lett.

      Volume: 40 Pages: 936-938

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] 窒素原子で架橋したジチエノピロール及びジベンゾチエノピロール誘導体の合成と物性評価2013

    • Author(s)
      光藤耕一、溝口 淳、菅 誠治
    • Organizer
      電気化学会創立80周年記念大会
    • Place of Presentation
      東北大学
    • Year and Date
      2013-03-30
    • Related Report
      2012 Final Research Report
  • [Presentation] ヘキサ-2-チエニルベンゼン誘導体の合成及びその電気化学的特性2013

    • Author(s)
      田中 陽、原田淳司、光藤耕一、菅 誠治
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学
    • Related Report
      2012 Final Research Report
  • [Presentation] 電気化学的な反応点制御に基づくビス(ジアリール)ブタジインの合成と材料化学への応用2013

    • Author(s)
      神本奈津代、光藤耕一、菅 誠治
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学
    • Related Report
      2012 Final Research Report
  • [Presentation] 電解法によって発生させた有機ジカチオン種を触媒とした反応開発2013

    • Author(s)
      大西由起、高須賀悠貴、岡村勇哉、藤原郁美、光藤耕一、菅 誠治
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学
    • Related Report
      2012 Final Research Report
  • [Presentation] Reactions Using Electrochemically Generated Organo-dications2012

    • Author(s)
      Seiji Suga
    • Organizer
      German-Japanese Meeting on Electrosynthesis
    • Place of Presentation
      Okayama Univ
    • Year and Date
      2012-08-18
    • Related Report
      2012 Final Research Report
  • [Presentation] わずかの電気量を通電するだけの有機電解反応2012

    • Author(s)
      菅 誠治
    • Organizer
      第47回有機反応若手の会
    • Place of Presentation
      岡山
    • Year and Date
      2012-08-02
    • Related Report
      2012 Final Research Report
  • [Presentation] レドックスシステムにより創製した有機活性種を用いる合成化学2011

    • Author(s)
      菅 誠治
    • Organizer
      有機合成セミナー「明日の有機合成化学」(有機合成化学協会関西支部)(招待講演)
    • Place of Presentation
      大阪科学技術センター
    • Related Report
      2011 Research-status Report
  • [Presentation] 有機電子移動反応により創製した活性種を利用するアルカロイドの立体選択的合成法2011

    • Author(s)
      菅 誠治
    • Organizer
      第42回中部化学関係学協会支部連合秋季大会(招待講演)
    • Place of Presentation
      信州大学
    • Related Report
      2011 Research-status Report
  • [Presentation] 高活性な有機カチオンを用いる合成化学2011

    • Author(s)
      菅 誠治
    • Organizer
      第27回若手研究者のための化学道場(有機合成化学協会)(招待講演)
    • Place of Presentation
      高知市かんぽの宿伊野
    • Related Report
      2011 Research-status Report
  • [Presentation] インダイレクトカチオンプール法を用いて発生させたN -アシルイミニウムイオンと有機リチウムの反応

    • Author(s)
      赤木智也・光藤耕一・菅誠治
    • Organizer
      第36 回有機電子移動化学討論会
    • Place of Presentation
      ルミエール府中(東京都)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 有機電子移動反応と反応プロセス制御

    • Author(s)
      菅誠治
    • Organizer
      第36 回有機電子移動化学討論会
    • Place of Presentation
      ルミエール府中(東京都)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Reactions Using Electrochemically Generated Organo-dications

    • Author(s)
      Suga, S.; Takasuka, Y.;Kawakami, M.; Onishi, Y.;Okamura, T.; Mitsudo, K.
    • Organizer
      6th Spanish Portuguese Japanese Organic Chemistry Symposium
    • Place of Presentation
      リスボン大学(ポルトガル)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Organic Reactions Mediated by Electrochemically Generated Species

    • Author(s)
      Suga, S.
    • Organizer
      French-Japanese “ Kinki-Divio Symposium”
    • Place of Presentation
      ブルゴーニュ大学(フランス)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] わずかの電気量を通電するだけの有機電解反応

    • Author(s)
      菅誠治
    • Organizer
      第47 回有機反応若手の会
    • Place of Presentation
      湯郷グランドホテル(岡山)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Reactions Using Electrochemically Generated Organo-dications

    • Author(s)
      Suga, S
    • Organizer
      German-Japanese Meeting on Electrosynthesis
    • Place of Presentation
      Johannes Gutenberg-Universitat Mainz(ドイツ)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] 電解法によって発生させた有機ジカチオン種を触媒とした反応開発

    • Author(s)
      大西由起・高須賀悠貴・岡村勇哉・藤原郁美・光藤耕一・菅 誠治
    • Organizer
      日本化学会第93 春季年会
    • Place of Presentation
      立命館大学(滋賀)
    • Related Report
      2012 Annual Research Report
  • [Remarks] RSK山陽放送 技術の森 ラジオ出演 2013年2月6日

    • Related Report
      2012 Final Research Report
  • [Patent(Industrial Property Rights)] 軸不斉を有するピリジン誘導体又はその塩、及びその製造方法並びにそれからなる不斉触媒2012

    • Inventor(s)
      菅誠治、萬代大樹
    • Industrial Property Rights Holder
      岡山大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2012-128070
    • Filing Date
      2012-06-22
    • Related Report
      2012 Annual Research Report
  • [Patent(Industrial Property Rights)] 架橋性ジチエノピロール化合物およびその重合体2011

    • Inventor(s)
      菅 誠治、光藤耕一他4名
    • Industrial Property Rights Holder
      岡山大学、株式会社クラレ
    • Industrial Property Number
      2011-138933
    • Filing Date
      2011
    • Related Report
      2011 Research-status Report
  • [Patent(Industrial Property Rights)] 縮合複素環化合物およびその重合体2011

    • Inventor(s)
      菅 誠治、光藤耕一他4名
    • Industrial Property Rights Holder
      岡山大学、株式会社クラレ
    • Industrial Property Number
      2011-138932
    • Filing Date
      2011
    • Related Report
      2011 Research-status Report

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

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