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2013 Fiscal Year Final Research Report

New deployment of the synthetic method utilized the characteristic of radical species

Research Project

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Project/Area Number 22590026
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionHyogo University of Health Sciences

Principal Investigator

MIYABE HIDETO  兵庫医療大学, 薬学部, 教授 (10289035)

Project Period (FY) 2010-04-01 – 2014-03-31
Keywords有機化学 / 合成化学 / ラジカル / 連続反応 / ルイス酸 / 酸化チタン
Research Abstract

The cascade or sequential reactions based on radical chemistry were investigated. I found that the sequential reaction of the intermediates arynes, generated from benzynes and formamides, with dialkylzinc proceeded. Next, I found that the cascade radical reactions, starting from the polarity-mismatched perfluoroalkyl radical addition to an electron-deficient acceptor, proceeded effectively. These reactions proceeded with good enantioselectivities by employing chiral Lewis acid. Additinally, the synthetically useful photocatalytic reduction of ketones was developed by using titanium dioxide.

  • Research Products

    (26 results)

All 2013 2012 2011 2010 Other

All Journal Article (9 results) (of which Peer Reviewed: 9 results) Presentation (12 results) Book (4 results) Remarks (1 results)

  • [Journal Article] Polarity-Mismatched Addition of Electrophilic Carbon Radicals to an Electron Deficient Acceptor : Cascade Radical Addition-Cyclization-Trapping Reaction2012

    • Author(s)
      Eito Yoshioka, Shigeru Kohtani, Kaori Sawai, Kentefu, Eri Tanaka, Hideto Miyabe
    • Journal Title

      J. Org. Chem.

      Volume: 77(19) Pages: 8588-8604

    • DOI

      10.1021/jo3015227

    • Peer Reviewed
  • [Journal Article] Adsorptive and Kinetic Properties on Photocatalytic Hydrogenation of Aromatic Ketones upon UV Irradiated Polycrystalline Titanium Dioxide : Differences between Acetophenone and its Trifluoromethylated Derivative2012

    • Author(s)
      Shigeru Kohtani, Eito Yoshioka, Kenji Saito, Akihiko Kudo, Hideto Miyabe
    • Journal Title

      J. Phy. Chem. C

      Volume: 116(33) Pages: 17705-17713

    • DOI

      10.1021/jp3056174

    • Peer Reviewed
  • [Journal Article] Insertion of Arynes into the Carbon-Oxygen Double Bond of Amides And Its Application into the Sequential Reactions2012

    • Author(s)
      Eito Yoshioka, Hideto Miyabe
    • Journal Title

      Tetrahedron

      Volume: 68(1) Pages: 179-189

    • DOI

      10.1016/j.tet.2011.10.072

    • Peer Reviewed
  • [Journal Article] Inter- and Intramolecular Carbon-Carbon Bond-Forming Radical Reactions2012

    • Author(s)
      Hideto Miyabe
    • Journal Title

      Synlett

      Volume: 23(12) Pages: 1709-1724

    • DOI

      10.1055/s-0031-1290378

    • Peer Reviewed
  • [Journal Article] Cascade Radical Reaction Induced by Polarity-Mismatched Perfluoroalkylation2011

    • Author(s)
      Eito Yoshioka, Kentefu, Xin Wang, Shigeru Kohtani, Hideto Miyabe
    • Journal Title

      Synlett

      Volume: (14) Pages: 2085-2089

    • DOI

      10.1055/s-0030-1261167

    • Peer Reviewed
  • [Journal Article] A Multicomponent Coupling Reaction Induced by Insertion of Arynes into C=O Bond of Formamide2011

    • Author(s)
      Eito Yoshioka, Shigeru Kohtani, Hideto Miyabe
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 50(29) Pages: 6638-6642

    • DOI

      10.1002/anie.201102088

    • Peer Reviewed
  • [Journal Article] Progress in Intermolecular Carbon Radical Addition to Imine Derivatives2010

    • Author(s)
      Hideto Miyabe, Eito Yoshioka, Shigeru Kohtani
    • Journal Title

      Current Organic Chemistry

      Volume: 14(12) Pages: 1254-1264

    • DOI

      10.2174/138527210791330477

    • Peer Reviewed
  • [Journal Article] Photocatalytic Hydrogenation of Acetophenone Derivatives and Diaryl Ketones on Polycrystalline Titanium Dioxide2010

    • Author(s)
      Shigeru Kohtani, Eito Yoshioka, Kenji Saito, Akihiko Kudo, Hideto Miyabe
    • Journal Title

      Catal. Commun.

      Volume: 11(13) Pages: 1049-1053

    • DOI

      10.1016/j.catcom.2010.04.022

    • Peer Reviewed
  • [Journal Article] Synthesis of Fluorinated Imines via Fluoroalkyl Radical Addition to Conjugated Imines2010

    • Author(s)
      Masafumi Ueda, Eri Iwasada, Hideto Miyabe, Okiko Miyata, Takeaki Naito
    • Journal Title

      Synthesis

      Volume: (12) Pages: 1999-2004

    • DOI

      10.1055/s-0029-1218755

    • Peer Reviewed
  • [Presentation] 鉄試薬を用いた酸化的ラクタム環形成反応の開発2013

    • Author(s)
      吉岡英斗、井元勇希、吉川知宏、甲谷繁、宮部豪人
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      パシフィコ横浜(横浜市)
    • Year and Date
      20130328-30
  • [Presentation] 酸化チタン表面での芳香族ケトンの光水素化反応初期過程-表面捕捉準位を介した電子移動機構-2012

    • Author(s)
      甲谷繁、鴨井佑奈、吉岡英斗、工藤昭彦、宮部豪人
    • Organizer
      第31回固体・表面光化学討論会
    • Place of Presentation
      大阪大学吹田キャンパス銀杏会館(吹田市)
    • Year and Date
      20121121-22
  • [Presentation] Dependence on Reduction Potential in the Photocatalytic Hydrogenation of Acetophenone Derivatives on Titanium Dioxide2012

    • Author(s)
      Shigeru Kohtani, Yuuna Kamoi, Eito Yoshioka, Akihiko Kudo, Hideto Miyabe
    • Organizer
      7th Asian Photochemistry Conference 2012
    • Place of Presentation
      Icho Kaikan in Osaka University (Osaka), Japan
    • Year and Date
      20121112-15
  • [Presentation] 水中での触媒的ラジカルカスケード反応の開発2012

    • Author(s)
      吉岡英斗、寺中孝久、深澤拓也、甲谷繁、宮部豪人
    • Organizer
      第38回反応と合成の進歩シンポジウム
    • Place of Presentation
      タワーホール船橋(東京都江戸川区)
    • Year and Date
      20121105-06
  • [Presentation] ベンザインからベンゾオキセテンを経由したジヒドロベンゾフラン類の合成2012

    • Author(s)
      吉岡英斗、甲谷繁、宮部豪人
    • Organizer
      第42回複素環化学討論会
    • Place of Presentation
      京都テルサ(京都市)
    • Year and Date
      20121011-13
  • [Presentation] 酸化チタン上での芳香族ケトンの光触媒的水素化反応における基質還元電位依存性2012

    • Author(s)
      甲谷繁、鴨井佑奈、吉岡英斗、工藤昭彦、宮部豪人
    • Organizer
      2012年光化学討論会
    • Place of Presentation
      東京工業大学岡山キャンパス(東京都)
    • Year and Date
      20120912-14
  • [Presentation] ベンザインとホルムアミドとの〔2+2〕型反応を基盤とした多成分連結反応2011

    • Author(s)
      吉岡英斗、甲谷繁、宮部豪人
    • Organizer
      第9回次世代を担う有機化学シンポジウム
    • Place of Presentation
      日本薬学会長井記念ホール(東京都)
    • Year and Date
      20110527-28
  • [Presentation] カスケード型ラジカル環化反応の選択性(2)2011

    • Author(s)
      吉岡英斗、澤井夏緒梨、田中絵理、甲谷繁、宮部豪人
    • Organizer
      第61回日本薬学会近畿支部総会大会
    • Place of Presentation
      神戸学院大学(神戸市)
    • Year and Date
      2011-10-22
  • [Presentation] Chiral Lewis Acid-Mediated Enantioselective Radical Cyclizations2011

    • Author(s)
      Hideto Miyabe
    • Organizer
      The 5th Pacific Symposium on Radical Chemistry (PSRC-5)
    • Place of Presentation
      Hotel Seamore in Shirahama (Wakayama), Japan
    • Year and Date
      2011-09-28
  • [Presentation] Enantioselective Cascade Radical Addition-Cyclization-Trapping Reactions2011

    • Author(s)
      Hideto Miyabe
    • Organizer
      The 2nd Annual World Congress of Catalytic Asymmetric Synthesis-2011
    • Place of Presentation
      Beijing International Convention Center (Beijing), China
    • Year and Date
      2011-08-09
  • [Presentation] Cascade radical iodoperfluoroalkylation for the synthesis of organofluorine compounds2010

    • Author(s)
      Hideto Miyabe, Eito Yoshioka、Shigeru Kohtani
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies [Pacifichem 2010]
    • Place of Presentation
      ハワイコンベンションセンター(Hawaii), USA
    • Year and Date
      20101215-21
  • [Presentation] Photocatalytic Hydrogenation of Aromatic Ketones on Titanium Dioxide2010

    • Author(s)
      Shigeru Kohtani, Eito Yoshioka, Kenji Saito, Akihiko Kudo, Hideto Miyabe
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies [Pacifichem 2010]
    • Place of Presentation
      ハワイコンベンションセンター(Hawaii), USA
    • Year and Date
      20101215-21
  • [Book] Photocatalytic Hydrogenation on Semiconductor Particles. In Hydrogenation. Ed. Karamé, I.2012

    • Author(s)
      Shigeru Kohtani, Eito Yoshioka, Hideto Miyabe
    • Total Pages
      291-308
    • Publisher
      INTECH : Croatia
  • [Book] Progress in Iridium-Catalyzed Allylic Substitutions. In Iridium : Occurrence, Characteristics and Applications. Eds. Fukui, C. Ono, M.2012

    • Author(s)
      Hideto Miyabe
    • Total Pages
      113-138
    • Publisher
      Nova Science Pub Inc : NY
  • [Book] 4.15 C-C Bond Formation (Radical). In Comprehensive Chirality. In Volume 4 (Synthetic Methods III - Catalytic Methods : C-C Bond Formation), Eds. Yamamoto, H. Carreira, E.2012

    • Author(s)
      Hideto Miyabe, Takeaki Naito
    • Total Pages
      303-314
    • Publisher
      ELSEVIER Ltd : UK
  • [Book] Chapter 5: Pyran and Its Derivatives. In Heterocycles in Natural Product Synthesis. Eds. Majumdar, K. C.; Chattopadhyay, S. K.2011

    • Author(s)
      Hideto Miyabe, Okiko Miyata, Takeaki Naito
    • Total Pages
      153-186
    • Publisher
      WILEY-VCH : Weinheim
  • [Remarks]

    • URL

      http://www2.huhs.ac.jp/~h070012h/

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Published: 2015-07-16  

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