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2009 Fiscal Year Final Research Report

Development of Innovative Radical Reactions by Means of Species Hybridization

Research Project

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Project/Area Number 19350051
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

RYU Ilhyong  Osaka Prefecture University, 理学系研究科, 教授 (80210821)

Co-Investigator(Kenkyū-buntansha) FUKUYAMA Takahide  大阪府立大学, 理学系研究科, 講師 (60332962)
MATSUBARA Hiroshi  大阪府立大学, 理学系研究科, 准教授 (20239073)
KOBAYASHI Shoji  大阪府立大学, 理学系研究科, 助教 (30374903)
Project Period (FY) 2007 – 2009
Keywordsラジカル反応 / ハイブリッド型連鎖反応 / 環境調和型反応プロセス / イオン反応 / 遷移金属触媒反応 / カルボニル化反応
Research Abstract

This research aimed at development of new radical reactions in which both radical species and non-radical species play a key role. Borohydride reagents proved to function as efficient radical mediators. As a notable example, hydroxymethylation of iodoalkanes proceeded using atmospheric pressure of CO and tertrabutylammonium borohydride. Under photo-irradiation conditions, in the presence of Pd complexes, three component coupling reaction of iodoalkanes, CO and terminal alkynes proceeded efficiently to give good yields of acetylenic ketones. Lactol forming reaction was also attained via ionic trapping of acyl radicals by an internal hydroxy group.

  • Research Products

    (37 results)

All 2010 2009 2008 2007 Other

All Journal Article (21 results) (of which Peer Reviewed: 20 results) Presentation (16 results)

  • [Journal Article] Black-Light-Induced Radical / Ionic Hydroxymethylation of Alkyl Iodides with Atmospheric CO in the Presence of Tetrabutylammonium Borohydride2010

    • Author(s)
      S. Kobayashi, T. Kawamoto, S. Uehara, T. Fukuyama, I. Ryu
    • Journal Title

      Org. Lett 12巻

      Pages: 1548-1551

    • Peer Reviewed
  • [Journal Article] StannylCarbonylation of Hydroxy-substituted Alkynes. Intramoleuclar Trapping ofα-Ketenyl Radicals by a Hydroxy Group Leading to Lactols2010

    • Author(s)
      I. Ryu, T. Fukuyama, O. Nobuta, Y. Uenoyama
    • Journal Title

      Bull. Korean Chem. Soc 31巻

      Pages: 545-546

    • Peer Reviewed
  • [Journal Article] Novel Radical Cyclization Method Accompanied by Elimination of Hydrazyl Radical2010

    • Author(s)
      S. Kobayashi, H. Hirao, T. Kawauchi, I. Ryu
    • Journal Title

      Heterocycles 80巻

      Pages: 879-885

    • Peer Reviewed
  • [Journal Article] Synthesis of 2-Hydroxymethyl Ketones by Ruthenium Hydride-Catalyzed Cross-Coupling Reaction ofα, β-Unsaturated Aldehydes with Primary Alcohols2010

    • Author(s)
      A. Denichoux, T. Fukuyama, T. Doi, J. Horiguchi, I. Ryu
    • Journal Title

      Org. Lett 12巻

      Pages: 1-3

    • Peer Reviewed
  • [Journal Article] Hydroruthenation Triggered Catalytic Conversion of Dialdehydes and Keto Aldehydes to Lactones2009

    • Author(s)
      S. Omura, T. Fukuyama, Y. Murakami, H. Okamoto, I. Ryu
    • Journal Title

      Chem. Commun

      Pages: 6741-6743

    • Peer Reviewed
  • [Journal Article] Addition of Allyl Bromide to Phenylacetylene Catalyzed by Palladium on Alumina and its Application to a Continuous Flow Synthesis2009

    • Author(s)
      T. Fukuyama, T. Kippo, I. Ryu, T. Sagae
    • Journal Title

      Res. Chem. Intermediate 35巻

      Pages: 1053-1057

    • Peer Reviewed
  • [Journal Article] Microflow Radical Carboaminoxylations with a Novel Alkoxyamine2009

    • Author(s)
      C. Wienhoefer, A. Studer, M.T. Rahahman, T. Fukuyama, I. Ryu
    • Journal Title

      Org. Lett 11巻

      Pages: 2457-2460

    • Peer Reviewed
  • [Journal Article] Organocatalytic Enantioselective Synthesis of Nitrogen-Substituted Dihydropyran-2-ones, a Key Synthetic Intermediate of 1β-Methylcarbapenems2009

    • Author(s)
      S. Kobayashi, T. Kinoshita, H. Uehara, T. Sudo, I. Ryu
    • Journal Title

      Org. Lett 11巻

      Pages: 3934-3937

    • Peer Reviewed
  • [Journal Article] An Automated-Flow Microreactor System for Quick Optimization and Production: Application of 10-and 100-gram Order Productions of a Matrix Metalloproteinase Inhibitor Using a Sonogashira Coupling Reaction2009

    • Author(s)
      Sugi moto, T. Fukuyama, M.T. Rahaman, I. Ryu
    • Journal Title

      Tetrahedron Lett 50巻

      Pages: 6364-6367

    • Peer Reviewed
  • [Journal Article] Radical Carbonylations Using a Continuous Microflow System2009

    • Author(s)
      T. Fukuyama, M.T. Rahman, N. Kamata, I. Ryu
    • Journal Title

      Beilstein J. Org. Chem 5巻

    • Peer Reviewed
  • [Journal Article] Ruthenium Hydride-Catalyzed Addition of Aldehydes to Dienes Leading to β, γ-Unsaturated Ketones2009

    • Author(s)
      S. Omura, T. Fukuyama, J. Horiguchi, Y. Murakami, I. Ryu
    • Journal Title

      J. Am. Chem. Soc 130巻

      Pages: 14094-14095

    • Peer Reviewed
  • [Journal Article] Microflow Photo-radical Reaction Using a Compact Light Source: Application to the Barton Reaction Leading to a Key Intermediate for Myriceric Acid A2009

    • Author(s)
      A. Sugimoto, T. Fukuyama, Y. Sumino, M. Takagi, I. Ryu
    • Journal Title

      Tetrahedron 65巻

      Pages: 1593-1598

    • Peer Reviewed
  • [Journal Article] Adventures in inner space: Microflow systems for practical organic synthesis2008

    • Author(s)
      T. Fukuyama, M.T. Rahman, M. Sato, I. Ryu
    • Journal Title

      Synlett

      Pages: 151-163

    • Peer Reviewed
  • [Journal Article] Spurring Radical Reactions of Organic Halides with Tin Hydride and TTMSS Using Microreactors2008

    • Author(s)
      T. Fukuyama, M. Kobayashi, M.T. Rahaman, N. Kamata, I. Ryu
    • Journal Title

      Org. Lett 10巻

      Pages: 533-536

    • Peer Reviewed
  • [Journal Article] Tin-Free Giese Reaction and the Related Radical Carbonylation Using Alkyl Iodides and Cyanoborohydrides2008

    • Author(s)
      I. Ryu, S. Uehara, H. Hirao, T. Fukuyama
    • Journal Title

      Org. Lett 10巻

      Pages: 1005-1008

    • Peer Reviewed
  • [Journal Article] Aerobic oxidation of cyclohexane using N-hydroxyphthalimide bearing fluoroalkyl chains2008

    • Author(s)
      S.K. Guha, Y. Obora, D. Ishihara, H. Matsubara, I. Ryu, Y. Ishii
    • Journal Title

      Adv. Synth. Catal 350巻

      Pages: 1323-1330

    • Peer Reviewed
  • [Journal Article] Radical Chain Reactions Using THP as a Solvent2008

    • Author(s)
      H. Yasuda, Y. Uenoyama, O. Nobuta, S. Kobayashi, I. Ryu
    • Journal Title

      Tetrahedron Letters 49巻

      Pages: 367-370

    • Peer Reviewed
  • [Journal Article] Phase-Vanishing Methods Based on Fluorous Phase Screen: A Simple Way for Efficient Execution of Organic Synthesis2008

    • Author(s)
      I. Ryu, H. Matsubara, H. Nakamura, D.P. Curran
    • Journal Title

      Chem. Rec 8巻

      Pages: 351-363

  • [Journal Article] Cyclopropanation of Alkenes with CH2I2/Et3Al by the Phase-vanishing Method Based on Fluorous Phase Screen2008

    • Author(s)
      H. Matsubara, M. Tsukida, S. Yasuda, I. Ryu
    • Journal Title

      J. Fluorine Chem 129巻

      Pages: 951-954

    • Peer Reviewed
  • [Journal Article] Chiral and achiral lithium amides having a fluorous ponytail: Preparation and evaluation as a recycling reagent for lithium enolate generation2007

    • Author(s)
      H. Matsubara, L. Maeda, H. Sugiyama, I. Ryu
    • Journal Title

      Synthesis

      Pages: 2901-2912

    • Peer Reviewed
  • [Journal Article] マルチタスク触媒:ルテニウムヒドリドによる原子効率型結合形成反応

    • Author(s)
      福山高英, 大村倉平, 柳日馨
    • Journal Title

      有機合成化学協会誌 (印刷中)

    • Peer Reviewed
  • [Presentation] アルキンとアミジンと一酸化炭素のラジカル反応を利用した三成分連結型ラクタム環構築法2010

    • Author(s)
      柳日馨
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      大阪
    • Year and Date
      2010-03-27
  • [Presentation] マイクロリアクターを用いた光ラジカル環化反応2010

    • Author(s)
      柳日馨
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      大阪
    • Year and Date
      2010-03-27
  • [Presentation] ラジカル条件化でのアルキン類のブロモアリル化反応2010

    • Author(s)
      柳日馨
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      大阪
    • Year and Date
      2010-03-27
  • [Presentation] ヒドリド活性種が関与する新規な炭素-炭素結合形成法2009

    • Author(s)
      柳日馨
    • Organizer
      平成21年度北陸地区講演会と研究発表会
    • Place of Presentation
      石川
    • Year and Date
      2009-11-28
  • [Presentation] Recent Advances in Metal Assisted Radical Cascade Reactions2009

    • Author(s)
      Ilhyong Ryu
    • Organizer
      The 4th Pacific Symposium on Radical Chemistry (PSRC-4)
    • Place of Presentation
      中国
    • Year and Date
      2009-11-19
  • [Presentation] ヒドリド活性種を活用する新しい炭素-炭素結合形成反応2009

    • Author(s)
      柳日馨
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      石川
    • Year and Date
      2009-11-16
  • [Presentation] グリーンな反応メディアによる有機合成戦略2009

    • Author(s)
      柳日馨
    • Organizer
      第40回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      岐阜
    • Year and Date
      2009-11-07
  • [Presentation] Continuous Microflow Systems for Greener Organic Synthesis2009

    • Author(s)
      Ilhyong Ryu
    • Organizer
      4th International Workshop on Chemistry, Polymers, Chemical Technology and Bio Technology for a Sustainable Future
    • Place of Presentation
      オランダ
    • Year and Date
      2009-09-13
  • [Presentation] Perfluorinated Ethers as Novel Reaction Media for Greener Chemical Synthesis and Processes2009

    • Author(s)
      Ilhyong Ryu
    • Organizer
      19th International Symposium on Fluorine Chemistry including ISoFT'09
    • Place of Presentation
      アメリカ
    • Year and Date
      2009-08-23
  • [Presentation] 脱有機溶媒型新反応メディアで何が出来るか:現状を展望2009

    • Author(s)
      柳日馨
    • Organizer
      平成21年度前期(春季)有機合成化学講習会
    • Place of Presentation
      東京
    • Year and Date
      2009-06-17
  • [Presentation] ルテニウム触媒存在下、エナミンとプロパルギルエステルとの反応による新規ピロール誘導体合成法2009

    • Author(s)
      柳日馨
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2009-03-27
  • [Presentation] α, β-不飽和アシルラジカルによる三級アミン窒素上での置換反応2009

    • Author(s)
      柳日馨
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2009-03-27
  • [Presentation] ヘリセノン類の全合成研究2009

    • Author(s)
      柳日馨
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2009-03-27
  • [Presentation] Greener Radical Process. Borohydride-Based Tin-Free Radical C-C Bond Forming Reactions2008

    • Author(s)
      I lhyong Ryu
    • Organizer
      10th International Symposium on Organic Free Radicals (ISOFR10)
    • Place of Presentation
      オーストラリア
    • Year and Date
      2008-08-05
  • [Presentation] スズを用いないラジカルヒドロキシメチル化反応2008

    • Author(s)
      柳日馨
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      東京
    • Year and Date
      2008-03-28
  • [Presentation] ルコキシアミンを用いたマイクロフロー系でのラジカル反応2008

    • Author(s)
      柳日馨
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      東京
    • Year and Date
      2008-03-26

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Published: 2011-06-18   Modified: 2016-04-21  

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