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Novel Preparation of Ion-supported Triphenylphosphines and Their Synthetic Utility

Research Project

Project/Area Number 20550033
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionChiba University

Principal Investigator

TOGO Hideo  Chiba University, 大学院・理学研究科, 教授 (60217461)

Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2010: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2009: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2008: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywordsトリフェニルホスフィン / Mitsunobu反応 / Appel反応 / Mizoroki-Heck反応 / Sonogashira反応 / Wittig反応 / 再生再利用 / イオン固定 / イオン液体 / アルデヒド / アルケン / トリフェニルホスフィンオキシド / イオンン液体 / トリフェニルホスフン / ハロゲン化反応 / 再利用 / エステル化反応 / 環境
Research Abstract

Novel ion-supported Ph3P compounds, 4-(diphenylphosphino)-benzyltrimethylammonium bromide (A) and N-methyl-N-[4-(diphenylphosphino) -benzyl]pyrrolidinium bromide (B), were prepared, and they were used for the esterification of carboxylic acid with the Mitsunobu reaction, and the Wittig reaction as a stoichiometoric reagent, and the Mizoroki-Heck reaction and the Sonogashira reaction for ligand with Pd. The advantages of using these ion-supported Ph_3P A and B are the simple isolation of the products by ether extraction due to their poor solubility in ether, and the easy recovery of the co-product, ion-supported Ph_3PO, by filtration in high yields (>90%), which could be regenerated and reused for the same reactions.

Report

(4 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (26 results)

All 2011 2010 2009 2008 Other

All Journal Article (13 results) (of which Peer Reviewed: 11 results) Presentation (5 results) Book (3 results) Remarks (1 results) Patent(Industrial Property Rights) (4 results)

  • [Journal Article] Wittig reaction with Ion-supported Ph3P2011

    • Author(s)
      N.Shimojuh, Y.Imura, K.Moriyama, H.Togo
    • Journal Title

      Tetrahedron 67

      Pages: 951-957

    • Related Report
      2010 Final Research Report
  • [Journal Article] Novel Preparation of Ion-supported Triphenylphosphines and Their Synthetic Utility2010

    • Author(s)
      M.Imura, N.Shimojuh, Y.Kawano, H.Togo
    • Journal Title

      Tetrahedron 66

      Pages: 3421-3426

    • Related Report
      2010 Final Research Report
  • [Journal Article] Metal-free One-pot Conversion of Electron-rich Arimatics into Aromatic Nitriles2010

    • Author(s)
      S.Ushijima, H.Togo
    • Journal Title

      Synlett

      Pages: 1067-1070

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Novel Preparation of Ion-supported Triphenylphosphines and Their Synthetic Utility2010

    • Author(s)
      M.Imura, N.Shimojuh, H.Togo
    • Journal Title

      Tetrahedron

      Volume: 66 Pages: 3421-3426

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Sulfonylamidation of Alkylbenzenes at Benzylic Position with p-Toluenesulfonamides and l, 3-Diiodo-5, 5-dimethylhyadntoin2010

    • Author(s)
      H.Baba, H.Togo
    • Journal Title

      Tetrahedron Letters

      Volume: 51 Pages: 2063-2066

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] One-pot Conversion of Aromatic Bromides and Aromatics into Aromatic Nitriles2010

    • Author(s)
      S.Ushijima, H.Togo
    • Journal Title

      Synlett

      Pages: 1562-1566

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 4-MeC6H4-Mediated Efficient α-Tosyloxylation of Ketones with Oxone and p-Toluenesulfonic Acid in Acetonitrile2009

    • Author(s)
      A.Tanaka, H.Togo
    • Journal Title

      Synlett

      Pages: 3360-3364

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ion-Supported PhI-Catalyzed Cyclization of N-Methoxy-2-arylethane-sulfonamides with mCPBA2009

    • Author(s)
      Ishwata, H.Togo
    • Journal Title

      Tetrahedron Letters 50

      Pages: 5354-5357

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 3-Exo-tet Cyclization of 2,2-Disubstituted 1,3-Dihalopropanes with Indium in Aqueous and Ionic Liquid Solvent System2009

    • Author(s)
      Y.Tsuchiya, Y.Izumisawa, H.Togo
    • Journal Title

      Tetrahedron 65

      Pages: 7533-7537

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Oxidative Conversion of Alkyl Halides into Nitriles with Molecular Iodine and 1,3-Diiodo-5,5-dimethylhydantoin in Ammonia2009

    • Author(s)
      S.Iida, R.Ohmaura, H.Togo
    • Journal Title

      Tetrahedron 65

      Pages: 6257-6262

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iodoarene-mediated One-pot Preparation of 2, 4, 5-Trisubstituted Oxazoles from Ketones2008

    • Author(s)
      Y. Kawano and H. Togo,
    • Journal Title

      Synlett

      Pages: 217-220

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iodobenzene-Catalyzed Preparation of 3,4-Dihydro-1H-2, 1-benzothiazine 2,2-Dioxide from 2-Aryl-N-methoxyethane sulfonamides with m-Chloroperoxybenzoic Acid2008

    • Author(s)
      A. Moroda and H. togo,
    • Journal Title

      Synthesis

      Pages: 1257-1261

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Radical 3-exo-tet Cyclization of 1, 3-Dihalopropanes with SmI2 to form Cyclopropanes2008

    • Author(s)
      T, Ohkita, Y. Tsuchiya, and H. Togo,
    • Journal Title

      Tetrahedron 64

      Pages: 7247-7251

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] 新規イオン固定型トリフェニルホスフィンの開発とWittig反応への展開2011

    • Author(s)
      伊村有未、下重直也、森山克彦、東郷秀雄
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      神奈川大学
    • Related Report
      2010 Final Research Report
  • [Presentation] 単体ヨウ素を用いた環境調和型有機反応の開発2010

    • Author(s)
      東郷秀雄
    • Organizer
      2010プロセス化学セミナー
    • Place of Presentation
      東京ビッグサイト
    • Year and Date
      2010-04-21
    • Related Report
      2010 Annual Research Report
  • [Presentation] 新規イオン液体固定型トリフェニルホスフィンの開発と有機合成化学的展開2010

    • Author(s)
      伊村有未、下重直也、東郷秀雄
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Related Report
      2010 Final Research Report
  • [Presentation] 単体ヨウ素及びDIHを用いたアルコール、アミン、及びハロゲン化物のニトリルへのワンポット変換反応2009

    • Author(s)
      東郷秀雄
    • Organizer
      日本プロセス化学会(招待講演)
    • Place of Presentation
      京都ホテル
    • Year and Date
      2009-12-04
    • Related Report
      2009 Annual Research Report
  • [Presentation] 単体ヨウ素及びDHIを用いたアルコール、アミン、及びハロゲン化物のニトリルへの変換反応2008

    • Author(s)
      東郷秀雄
    • Organizer
      第93有機合成シンポジウム
    • Place of Presentation
      東京工業大学
    • Year and Date
      2008-06-13
    • Related Report
      2008 Annual Research Report
  • [Book] 新訂版 有機反応のしくみと考え方2010

    • Author(s)
      東郷秀雄
    • Total Pages
      387
    • Publisher
      講談社サイエンティフィック
    • Related Report
      2010 Annual Research Report
  • [Book] 基礎有機化学2009

    • Author(s)
      東郷秀雄
    • Total Pages
      250
    • Publisher
      東京化学同人
    • Related Report
      2009 Annual Research Report
  • [Book] 基礎有機化学、身近な有機化合物を中心に2009

    • Author(s)
      東郷秀雄
    • Total Pages
      245
    • Publisher
      東京化学同人
    • Related Report
      2008 Annual Research Report
  • [Remarks] ホームページ等

    • Related Report
      2010 Final Research Report
  • [Patent(Industrial Property Rights)] 新規イオン液体固定型第三級ホスフィン2010

    • Inventor(s)
      東郷秀雄、伊村有未
    • Industrial Property Rights Holder
      東郷秀雄、伊村有未
    • Industrial Property Number
      2010-011476
    • Filing Date
      2010-01-21
    • Related Report
      2010 Final Research Report
  • [Patent(Industrial Property Rights)] 千葉大学2010

    • Inventor(s)
      東郷秀雄、牛島荘輔
    • Industrial Property Rights Holder
      千葉大学
    • Industrial Property Number
      2010-116777
    • Filing Date
      2010-05-20
    • Related Report
      2010 Annual Research Report
  • [Patent(Industrial Property Rights)] 千葉大学2010

    • Inventor(s)
      東郷秀雄、牛島荘輔
    • Industrial Property Rights Holder
      千葉大学
    • Industrial Property Number
      2010-035162
    • Filing Date
      2010-02-15
    • Related Report
      2009 Annual Research Report
  • [Patent(Industrial Property Rights)] 千葉大学2008

    • Inventor(s)
      東郷秀雄
    • Industrial Property Rights Holder
      千葉大学
    • Industrial Property Number
      2008-233460
    • Filing Date
      2008-07-21
    • Related Report
      2008 Annual Research Report

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Published: 2008-04-01   Modified: 2016-04-21  

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