• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Catalytic C-C Bond Cleavage Reactions of Acyclic Alkanes

Research Project

Project/Area Number 15K13699
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, 21世紀科学研究機構, 教授 (80210821)

Co-Investigator(Kenkyū-buntansha) 福山 高英  大阪府立大学, 理学(系)研究科(研究院), 准教授 (60332962)
Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywordsイリジウム触媒 / 水素化分解 / 炭素ー炭素結合切断 / 直鎖状アルカン / 環状アルカン / メタン合成 / アルミナ / 遷移金属触媒 / C-C結合開裂 / 水素化 / メタン / 減炭反応 / イリジウム
Outline of Final Research Achievements

Catalytic cleavage of C-C bonds is familiar for highly strained compounds. However, the C-C bond cleavage of non-strained linear alkanes is not common. This work focused on the finding of a useful catalytic system for C-C bond cleavage available for non-strained linear alkanes. After the survey of the catalytic systems, iridium catalyst was found to show excellent catalytic activity for C-C bond cleavage of linear alkanes, such as nonadecane under hydrogen atmosphere at heated conditions (250-270°C). The reaction completed with the complete conversion to methane. The time course experiment revealed that C-C cleavage took place from the edge. The catalytic C-C cleavage reaction was successfully applied to cyclododecane, which proceeded via hydrogenative ring-opening. The catalyst can be used at least four times without loss in the activity.

Report

(3 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • Research Products

    (24 results)

All 2017 2016 2015

All Journal Article (12 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 12 results,  Acknowledgement Compliant: 10 results) Presentation (11 results) (of which Int'l Joint Research: 5 results,  Invited: 5 results) Book (1 results)

  • [Journal Article] Flow Dehydration and Hydrogenation of Allylic Alcohols: Application to the Waste-Free Synthesis of Pristane2017

    • Author(s)
      Furuta, A.; Hirobe, Y.; Fukuyama, T.; Ryu, I.
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2017 Issue: 10 Pages: 1365-1368

    • DOI

      10.1002/ejoc.201700072

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Versatile cross-dehydrogenative coupling of heteroaromatics and hydrogen donors via decatungstate photocatalysis2017

    • Author(s)
      Wuattrini, M. C.; Fujii, S.; Yamada, K.; Fukuyama, T.; Ravelli, D.; Fagnoni, M.; Ryu, I.
    • Journal Title

      Chem. Commun.

      Volume: 53 Issue: 15 Pages: 2335-2338

    • DOI

      10.1039/c6cc09725a

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] A Palladium/Light System Combined with Hanztsch Ester: Radical Vinylation of Alkyl Iodides with Vinyl Bromides2017

    • Author(s)
      Sumino, S., *Ryu, I.
    • Journal Title

      Asian J. Org. Chem.

      Volume: 6 Issue: 4 Pages: 410-413

    • DOI

      10.1002/ajoc.201600547

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Formal Total Synthesis of l-Ossamine via Decarboxylative Functionalization Using Visible-Light-Mediated Photoredox Catalysis in a Flow System2017

    • Author(s)
      Inuki, S.; Sato, K.; Fukuyama, T.; Ryu, I.; Fujimoto, Y.
    • Journal Title

      J. Org. Chem.

      Volume: 82 Issue: 2 Pages: 1248-1253

    • DOI

      10.1021/acs.joc.6b02531

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 2,3-disubstituted indenones by cobalt-catalyzed [3+2] annulation of omethoxycarbonylphenylboronic acid with alkynes2016

    • Author(s)
      *Ueda, M., Ueno, T., Suyama, Y., Ryu, I.
    • Journal Title

      Chem. Commun.

      Volume: 52(90) Issue: 90 Pages: 13237-13240

    • DOI

      10.1039/c6cc08032d

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Regio- and stereo-selective intermolecular [2+2] cycloaddition of allenol esters with C60 leading to alkylidenecyclobutane-annulated fullerenes2016

    • Author(s)
      Mitsuhiro Ueda, Tsukasa Sakaguchi, Miho Hayama, Takafumi Nakagawa, Yutaka Matsuo, Aiko Munechika, Shunsuke Yoshida, Hiroshi Yasuda, Ilhyong Ryu
    • Journal Title

      Chem. Commun.

      Volume: 52 Issue: 89 Pages: 13175-13178

    • DOI

      10.1039/c6cc07320d

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Flow Update for a Cossy Photocyclization2016

    • Author(s)
      Fukuyama, T.; Fujita, Y.; Rashid, M. A.; Ryu, I.
    • Journal Title

      Org. Lett.

      Volume: 18 Issue: 20 Pages: 5444-5446

    • DOI

      10.1021/acs.orglett.6b02727

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] A greener process for flow C-H chlorination of cyclic alkanes using in situ generation and on-site consumption of chlorine gas2016

    • Author(s)
      Fukuyama, T.; Tokizane, M.; Matsui, A.; Ryu, I.
    • Journal Title

      React. Chem. Eng.

      Volume: 1 Issue: 6 Pages: 613-615

    • DOI

      10.1039/c6re00159a

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Transition-metal-free cross-coupling reaction of benzylic halides with arylboronic acids leading to diarylmethanes2016

    • Author(s)
      *Ueda, M., Nakakoji, D., Kuwahara, Y., Nishimura, K., Ryu, I.
    • Journal Title

      Tetrahedron Lett.

      Volume: 57(37) Issue: 37 Pages: 4142-4144

    • DOI

      10.1016/j.tetlet.2016.07.089

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Radical bromoallylation of alkynes leading to 1-bromo-1,4-dienes2016

    • Author(s)
      Kippo, T., Hamaoka, K., Ueda, M., Fukuyama, T., *Ryu, I.
    • Journal Title

      Tetrahedron

      Volume: 72(48) Issue: 48 Pages: 7866-7874

    • DOI

      10.1016/j.tet.2016.05.084

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Palladium-Catalyzed Carbonylative Couplings of Vinylogous Enolates: Application to Statin Structures2015

    • Author(s)
      Makarov, I. S.; Kuwahara, T.; Jusseau, X.; Ryu, I.; Lindhardt, A. T.; Skrydstrup, T.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 137 Issue: 44 Pages: 14043-14046

    • DOI

      10.1021/jacs.5b09342

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Intramolecular Carbolithiation of 3-Lithioxy-5-alkenyllithiums as a Platform for Cyclopentanols and Cyclopentanones2015

    • Author(s)
      Ryu, I.; Yamamura, G.; Minakata, S.; Komatsu, M.; Kubo, H.; Ueda, M.
    • Journal Title

      Synlett (Cluster)

      Volume: 26 Issue: 17 Pages: 2413-2417

    • DOI

      10.1055/s-0035-1560170

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] シリカゲル固定化3級アミン触媒を用いたシクロペンテン骨格を有するフラーレン誘導体のフロー合成2017

    • Author(s)
      端山 美帆・棟近 相衣子・植田 光洋・柳 日馨
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      kanagawa
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] ロジウム触媒存在下、ビアリールカルボン酸とアルキンとの脱カルボニル化を伴った環化反応によるフェナントレン誘導体の合成2017

    • Author(s)
      福山 高英・坂手 拓哉・柳 日馨
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      kanagawa
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] ロジウム触媒存在下、アントラニル酸のアルキンへのカルボアミノ化によるキノリノン類合成2017

    • Author(s)
      福山 高英・古川 拓宙・柳 日馨
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      kanagawa
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] ロジウム触媒によるチオサリチル酸とアルキンからのチオクロメノン合成2017

    • Author(s)
      福山 高英・杉森 大樹・柳 日馨
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      kanagawa
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Site-selective Conversion of sp3 C-H Bond to C-C Bond by Photo-catalyst2016

    • Author(s)
      Ilhyong Ryu
    • Organizer
      The 10th International Symposium on Integrated Synthesis(ISONIS-10)
    • Place of Presentation
      Hyogo
    • Year and Date
      2016-11-18
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Palladium/Light Induced Vinylation of Iodoalkanes2016

    • Author(s)
      Ilhyong Ryu
    • Organizer
      the 12th International Symposium on Organic Free Radicals (ISOFR12)
    • Place of Presentation
      Shanghai
    • Year and Date
      2016-10-09
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Recent Advances in Flow Catalysis2016

    • Author(s)
      Ilhyong Ryu
    • Organizer
      14th International Conference on Micro Reaction Technology (IMRET14)
    • Place of Presentation
      Beijin
    • Year and Date
      2016-09-12
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Aryl Radical Carbonylation Induced by Photo-irradiation2016

    • Author(s)
      Ilhyong Ryu
    • Organizer
      The 12th International Symposium on Organic Reactions(ISOR-12)
    • Place of Presentation
      kyoto
    • Year and Date
      2016-04-22
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Hydrodechlorination of Alkyl Chlorides Using Iridium Catalysts2016

    • Author(s)
      福山 高英・浜田 由希・柳 日馨
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] H2IrCl6触媒によるアルカンの水素化分解反応2016

    • Author(s)
      福山 高英・金子 将也・柳 日馨
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Flow Carbonylation by Reactive Intermediates2015

    • Author(s)
      Ilhyong Ryu
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Hawaii Convention Center, Honolulu, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Book] 有機合成実験法ハンドブック2015

    • Author(s)
      柳 日馨
    • Total Pages
      1202
    • Publisher
      丸善
    • Related Report
      2015 Research-status Report

URL: 

Published: 2015-04-16   Modified: 2018-03-22  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi