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Synthetic Chemistry of CO-RetainingMolecules

Research Project

Project/Area Number 23655088
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionOsaka Prefecture University

Principal Investigator

RYU Ilhyong  大阪府立大学, 理学系研究科, 教授 (80210821)

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ギ酸 / 硫酸 / NHC ボラン / 一酸化炭素 / カルボン酸 / 脱カルボニル化 / カルボニル化 / NHCボラン / ブレンステッド酸 / ヒドロキシメチル化 / ホウ素錯体 / ホルムアルデヒド / Koch-Haaf反応 / フロー反応
Research Abstract

Carbon monoxide (CO) plays a central role in carbonylation chemistry, however, the toxicity and the necessity of cautious handling have often prevented chemists to use CO for ordinary organic synthesis. In this study we focused on the use of potential CO retaining molecules for carbonylation reactions in the hope of providing useful carbonylation methods. The Morgan reaction comprising formic acids and sulfuric acid was examined in a gas permeable PTFE tube to generate CO, showing that acids stayed inside the tube and only CO gas came out from the tube. Flow carbonylation reaction system was created using a tube in tube system composed of an outer stainless-steel tube and an inner PTFE tube. In the outer tube, Pd-catalyzed carbonylation reaction took place to give the amide. In the presence of NHC・borane, hydroxymethylation of iodobenzene using CO was investigated under photo-irradiation conditions.

Report

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

    (30 results)

All 2013 2012 2011

All Journal Article (10 results) (of which Peer Reviewed: 10 results) Presentation (20 results)

  • [Journal Article] Rhodium-Catalyzed Decarbonylative C-H Arylation of 2-Aryloxybenzoic Acids Leading to Dibenzofuran Derivatives2013

    • Author(s)
      Maetani, S.; Fukuyama, T.; Ryu, I.
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 11 Pages: 2754-2757

    • DOI

      10.1021/ol4010905

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Modernized Low Pressure Carbonylation Methods in Batch and Flow Employing Common Acids as a CO Source2013

    • Author(s)
      Brancour, C.; Fukuyama, T.; Mukai, Y.; Skrydstrup, T.; Ryu, I.
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 11 Pages: 2794-2797

    • DOI

      10.1021/ol401092a

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Efficient Hydroxymethylation Reactions of Iodoarenes Using CO and 1,3-Dimethylimidazol-2-ylidene Borane2013

    • Author(s)
      Kawamoto,T.; Okada.T.; Curran,D.P.; Ryu,I
    • Journal Title

      Org.Lett

      Volume: 5巻 Pages: 2144-2147

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Efficient Hydroxymethylation Reactions of Iodoarenes Using CO and 1,3-Dimethylimidazol-2-ylidene Borane2013

    • Author(s)
      Kawamoto, Y.; Okada, T.; Curran, D. P.; Ryu, I.
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 9 Pages: 2144-2147

    • DOI

      10.1021/ol4006294

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 〓Total synthesis and structural revision of hericerin2012

    • Author(s)
      S. Kobayashi, T. Inoue, A. Ando, H.Tamanoi, I. Ryu, A. Masuyama
    • Journal Title

      J. Org. Chem.

      Volume: Vol.77 Issue: 13 Pages: 5819-5822

    • DOI

      10.1021/jo300719m

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Rh-Catalyzed[5+1] and [4+1] Cycloaddition Reaction of 1,4-Enyne Esters with CO. shortcut to Functionalized Resorcinols and Cyclopentenones2012

    • Author(s)
      Fukuyama,T.; Ohta,Y.; Brancour,C.; Miyagawa,K.; Ryu,I.; Dhimane,A.; Fensterbank,L.; Malacria,M
    • Journal Title

      Chem.-Eur.J

      Volume: 18巻 Pages: 7243-7247

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Radical Addition of Alkyl Halides to Formaldehyde in the Presence of Cyanoborohydride as a Radical Mediator. A New Protocol for Hydroxymethylation Reaction2012

    • Author(s)
      Kawamoto, T.; Fukuyama, T.; and Ryu, I
    • Journal Title

      Journal of the American Chemical Society

      Volume: 134 Issue: 2 Pages: 875-877

    • DOI

      10.1021/ja210585n

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Rh-Catalyzed [5+1] and [4+1] Cycloaddition Reaction of 1,4-Enyne Esters with CO. Shortcut to Functionalized Resorcinols and Cyclopentenones2012

    • Author(s)
      Fukuyama, T.; Ohta, Y.; Brancour, C.; Miyagawa, K.; Ryu, I.; Dhimane, A.; Fensterbank, L.; Malacria, M.
    • Journal Title

      Chem. -Eur. J.

      Volume: 18 Issue: 23 Pages: 7243-7247

    • DOI

      10.1002/chem.201200045

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Free-Radical Mediated Hydroxymethylation Using CO and HCHO2012

    • Author(s)
      Kawamoto, T.; Ryu, I.
    • Journal Title

      Chimia

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Koch-Haaf Reaction of Adamantanols in an Acid-tolerant Hastelloy-made Microreactor2011

    • Author(s)
      Fukuyama, T.; Mukai, Y.; Ryu, I.
    • Journal Title

      Beilstein J.Org.Chem.

      Volume: 7 Pages: 1288-1293

    • DOI

      10.3762/bjoc.7.149

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Presentation] 連続フローマイクロ系によるシリルアリルリチウムの発生とカルボニル化2013

    • Author(s)
      柳 日馨
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀
    • Year and Date
      2013-03-22
    • Related Report
      2012 Final Research Report
  • [Presentation] アリールヨージドのラジカルヒドロキシメチル化反応2013

    • Author(s)
      柳 日馨
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀
    • Year and Date
      2013-03-22
    • Related Report
      2012 Final Research Report
  • [Presentation] アルキルヨウ素化物と一酸化炭素とアリールボロン酸からのケトン合成2013

    • Author(s)
      柳 日馨
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀
    • Year and Date
      2013-03-22
    • Related Report
      2012 Final Research Report
  • [Presentation] トリエチルボランを用いたヨウ化アルキルのアセトアルデヒドへのラジカル付加反応2013

    • Author(s)
      柳 日馨
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀
    • Year and Date
      2013-03-22
    • Related Report
      2012 Final Research Report
  • [Presentation] ロジウム触媒を用いる2-アリロキシ安息香酸の脱カルボニル的環化反応によるジベンゾフラン類の合成2013

    • Author(s)
      柳 日馨
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀
    • Year and Date
      2013-03-22
    • Related Report
      2012 Final Research Report
  • [Presentation] 連続フローマイクロ系によるシリルアリルリチウムの発生とカルボニル化2013

    • Author(s)
      福山高英・十時丈典・柳 日馨
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀県
    • Related Report
      2012 Annual Research Report
  • [Presentation] アリールヨージドのラジカルヒドロキシメチル化反応2013

    • Author(s)
      岡田拓磨・川本拓治・柳日馨
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀県
    • Related Report
      2012 Annual Research Report
  • [Presentation] アルキルヨウ素化物と一酸化炭素とアリールボロン酸からのケトン合成2013

    • Author(s)
      隅野修平・宇井隆人・柳 日馨
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀県
    • Related Report
      2012 Annual Research Report
  • [Presentation] トリエチルボランを用いたヨウ化アルキルのアセトアルデヒドへのラジカル付加反応2013

    • Author(s)
      川本拓治・西田泰規・柳 日馨
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀県
    • Related Report
      2012 Annual Research Report
  • [Presentation] ロジウム触媒を用いる2-アリロキシ安息香酸の脱カルボニル的環化反応によるジベンゾフラン類の合成2013

    • Author(s)
      前谷臣治・福山高英・柳 日馨
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀県
    • Related Report
      2012 Annual Research Report
  • [Presentation] Free-Radical Hydroxyalkylation Reactions: Trapping of HCHO by Carbon Radicals2012

    • Author(s)
      Ilhyong Ryu
    • Organizer
      11th International Symposium on Organic Free Radicals (ISOFR-11)
    • Place of Presentation
      Berne
    • Year and Date
      2012-07-01
    • Related Report
      2012 Annual Research Report 2012 Final Research Report
  • [Presentation] Continuous Flow Microreactor for Efficiency in Organic Synthesis2012

    • Author(s)
      Ilhyong Ryu
    • Organizer
      2nd International Conference of the Flow Chemistry Society
    • Place of Presentation
      Germany
    • Year and Date
      2012-03-14
    • Related Report
      2012 Final Research Report
  • [Presentation] Continuous Flow Microreactor for Efficiency in Organic Synthesis2012

    • Author(s)
      Ilhyong Ryu
    • Organizer
      2nd International Conference of the Flow Chemistry Society(招待講演)
    • Place of Presentation
      Germany, Munich
    • Related Report
      2011 Research-status Report
  • [Presentation] フロー系反応デバイスによる有機合成:最近の進捗2011

    • Author(s)
      柳 日馨
    • Organizer
      日本プロセス化学会 2011 ウインターシンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2011-12-09
    • Related Report
      2012 Final Research Report
  • [Presentation] Tin-free One-carbon Homologation Reactions2011

    • Author(s)
      Ilhyong Ryu
    • Organizer
      Green Chemistry 2011 Innovations 3rd Asia-Oceania Conference on Green & Substainable Chemistry
    • Place of Presentation
      Australia
    • Year and Date
      2011-12-04
    • Related Report
      2012 Final Research Report
  • [Presentation] Radical Hydroxymethylation of Alkyl Halides Using Formaldehyde2011

    • Author(s)
      Ilhyong Ryu
    • Organizer
      The 36th Annual Synthesis Symposium
    • Place of Presentation
      Australia
    • Year and Date
      2011-12-02
    • Related Report
      2012 Final Research Report 2011 Research-status Report
  • [Presentation] Formaldehyde as a Radical Acceptor2011

    • Author(s)
      Ilhyong Ryu
    • Organizer
      5th Pacific Symposium on Radical Chemistry (PSRC-5)
    • Place of Presentation
      和歌山
    • Year and Date
      2011-09-25
    • Related Report
      2012 Final Research Report
  • [Presentation] フロー系反応デバイスによる有機合成:最近の進捗2011

    • Author(s)
      柳 日馨
    • Organizer
      日本プロセス化学会2011ウインターシンポジウム(招待講演)
    • Place of Presentation
      東京
    • Related Report
      2011 Research-status Report
  • [Presentation] Formaldehyde as a Radical Acceptor2011

    • Author(s)
      Takuji Kawamoto, Takahide Fukuyama, and Ilhyong Ryu
    • Organizer
      5th Pacific Symposium on Radical Chemistry(PSRC-5)
    • Place of Presentation
      和歌山
    • Related Report
      2011 Research-status Report
  • [Presentation] Tin-free One-carbon Homologation Reactions2011

    • Author(s)
      Takuji Kawamoto, Takahide Fukuyama, Ilhyong Ryu
    • Organizer
      Green Chemistry 2011 Innovations 3rd Asia-Oceania Conference on Green & Sustainable Chemistry
    • Place of Presentation
      Australia
    • Related Report
      2011 Research-status Report

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

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