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2013 Fiscal Year Final Research Report

Development of New Catalytic Reactions Directed to Straightforward Synthesis of Unused Carbon Sources

Research Project

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Project/Area Number 22245016
Research Category

Grant-in-Aid for Scientific Research (A)

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

Principal Investigator

CHATANI Naoto  大阪大学, 工学(系)研究科(研究院), 教授 (30171953)

Co-Investigator(Kenkyū-buntansha) YOSHIYA Fukumoto  大阪大学, 大学院工学研究科, 准教授 (50273595)
Co-Investigator(Renkei-kenkyūsha) MAMORU Tobisu  大阪大学, 大学院工学研究科, 准教授 (60403143)
Project Period (FY) 2010-04-01 – 2013-03-31
Keywords炭素資源 / 炭素-水素結合活性化 / 炭素-炭素結合活性化 / 炭素-酸素結合活性化 / 炭素-ケイ素結合活性化 / 炭素-フッ素結合活性化
Research Abstract

It was found that nickel complexes show high catalytic activity in Suzuki coupling, amination and reduction of anisole derivatives, which involve the activation of carbon-methoxy bonds. Silyl-rhodium species were found to be a superior catalytic active species for the activation of C-CN bonds. We found silylation, borylation, and phenylation reactions involving the cleavage of C-CN bonds. Based on these results, we successfully discovered a new synthesis of benzosiloles, which have interesting electronic properties. We found the Ru-catalyzed carbonylation of C(sp3)-H bonds in aliphatic amides that contain an 8-aminoquinoline directing group.

  • Research Products

    (23 results)

All 2012 2011 2010

All Journal Article (11 results) (of which Peer Reviewed: 11 results) Presentation (12 results)

  • [Journal Article] Rhodium-Catalyzed Carbon-Silicon Bond Activation for Synthesis of Benzosilole Derivatives, Onoe, M2012

    • Author(s)
      Baba, K.; Kim, Y.; Kita, Y.; Tobisu, M.; Chatani, N
    • Journal Title

      J. Am. Chem. Soc

      Volume: 134 Pages: 19477-19488

    • DOI

      10.1021/ja3096174

    • Peer Reviewed
  • [Journal Article] Modular Synthesis of Phenanthridine Derivatives via Oxidative Cylization of 2-Isocyanobiphenyls with Organoboron Reagents2012

    • Author(s)
      Tobisu, M.; Koh, K.; Furukawa, T.; Chatani, N
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 51 Pages: 11363-12366

    • DOI

      10.1002/anie.201206115

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Regio- and Stereoselective Addition of Imines toTerminal Alkynes Laeding to N-Alkylideneallylamines2012

    • Author(s)
      Fukumoto, Y.; Daijyo, M.; Chatani, N
    • Journal Title

      J. Am. Chem. Soc

      Volume: 134 Pages: 8762-8765

    • DOI

      10.1021/ja3022818

    • Peer Reviewed
  • [Journal Article] Rhodium(I)-Catalyzed Borylation of Nitriles through the Cleavage of Carbon‒Cyano Bonds2012

    • Author(s)
      Tobisu, M.; Kinuta, H.; Kita, Y.; Rémond, E.; Chatani, N
    • Journal Title

      J. Am. Chem. Soc

      Volume: 134 Pages: 115-118

    • DOI

      10.1021/ja2095975

    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Suzuki-Miyaura Reaction of Aryl Fluorides2011

    • Author(s)
      Tobisu, M.; Xu, T.; Shimasaki, T.; Chatani, N
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Pages: 19505-19511

    • DOI

      10.1021/ja207759e

    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Chelation-Assisted Transformations Involving the ortho C-H Bond Activation : The Regioselective Oxidative Cycloaddition of Aromatic Amides to Alkynes2011

    • Author(s)
      Shiota, H.; Ano, Y.; Aihara, Y.; Fukumoto, Y.; Chatani, N
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Pages: 14952-14955

    • DOI

      10.1021/ja206850s

    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Direct Ethynylation of C(sp^3)-H Bonds in Aliphatic Carboxylic Acid Derivatives2011

    • Author(s)
      Ano, Y.; Tobisu, M.; Chatani, N
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Pages: 12984-12986

    • DOI

      10.1021/ja206002m

    • Peer Reviewed
  • [Journal Article] Switch in Stereoselectivity Caused by the Isocyanide Structure in the Rhodium- Catalyzed Silylimination of Alkynes2011

    • Author(s)
      Fukumoto, Y.; Hagihara, M.; Kinashi, F.; Chatani, N
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Pages: 10014-10017

    • DOI

      10.1021/ja202881y

    • Peer Reviewed
  • [Journal Article] Highly Regioselective Carbonylation of Unactivated C(sp^3)-H Bonds by Ruthenium Carbonyl2011

    • Author(s)
      Hasegawa, N.; Charra, V.; Inoue, S.; Fukumoto, Y.; Chatani, N
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Pages: 8070-8073

    • DOI

      10.1021/ja2001709

    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Cyclization of Difluoro-Substituted 1,6-Enynes with Organozinc Reagents Leading to through the Stereoselective Activation of C-F Bonds : Synthesis of Bicyclo[3.2.0]heptene Derivatives2010

    • Author(s)
      Takachi, M.; Kita, Y.; Tobisu, M.; Fukumoto, Y.; Chatani, N
    • Journal Title

      Angew. Chem., Int. Ed

      Volume: 49 Pages: 8717-8720

    • DOI

      10.1002/anie.201004543

    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Amination of Aryl Carboxylates via the Cleavage of Aryl-Oxygen Bonds2010

    • Author(s)
      Shimasaki, T.; Tobisu, M.; Chatani, N
    • Journal Title

      Angew. Chem., Int. Ed

      Volume: 49 Pages: 2929-2932

    • DOI

      10.1002/anie.200907287

    • Peer Reviewed
  • [Presentation] Cross-Coupling Reactions Involving C-O Bond Activation2012

    • Author(s)
      Chatani, N
    • Organizer
      1st International Conference on Organometallics and Catalysis
    • Place of Presentation
      Beijing, China
    • Year and Date
      20121000
  • [Presentation] Chelation-Assisted Transformations Involving C-H Bond Activation2012

    • Author(s)
      Chatani, N
    • Organizer
      The 1st International Symposium on C-H Activation
    • Place of Presentation
      Beijing, China
    • Year and Date
      20121000
  • [Presentation] Catalytic Reactions Involving Activation of Unreactive Bonds2012

    • Author(s)
      Chatani, N
    • Organizer
      The 6th Kansai-CMDS Meeting on OMCOS
    • Place of Presentation
      Sorak Mt., Korea
    • Year and Date
      20120900
  • [Presentation] Transformations Involving C-H Bond Activation Utilizing a Bidentate Directing System2012

    • Author(s)
      Chatani, N
    • Organizer
      7th Asian-European Symposium on Metal-Mediated Efficient Organic Synthesis
    • Place of Presentation
      Tarragona, Spain
    • Year and Date
      20120700
  • [Presentation] Catalytic Transformations Involving Activation of Unreactive Bonds2012

    • Author(s)
      Chatani, N
    • Organizer
      6th Spanish-Portuguese-Japanese Organic Chemistry Symposium (6th SPJ-OCS)
    • Place of Presentation
      Lisbon, Portugal
    • Year and Date
      20120700
  • [Presentation] Chelation-Assisted Transformations Involving C-H Bond Activation2012

    • Author(s)
      Chatani, N
    • Organizer
      18th International Symposium on Homogeneous Catalysis (ISHC-XVIII)
    • Place of Presentation
      Toulouse, France
    • Year and Date
      20120700
  • [Presentation] Transformations Involving Activation of C-H Bonds Utilizing a Bidentate Directing System2012

    • Author(s)
      Chatani, N
    • Organizer
      International Conference on Functional Organic Materials and Related Devices
    • Place of Presentation
      Hsinchu , Taiwan
    • Year and Date
      20120600
  • [Presentation] Regioselective Carbonylation of Unactivated C(sp^3)-H Bonds Catalyzed by Ru^3(CO)^<12>2011

    • Author(s)
      Chatani, N
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2011 (C&FC2011)
    • Place of Presentation
      Nara, Japan
    • Year and Date
      20111200
  • [Presentation] Regioselective Carbonylation of Unactivated C(sp^3)-H Bonds in Aliphatic Amides2011

    • Author(s)
      Chatani, N
    • Organizer
      10th International Symposium on Organic Reactions (ISOR-2011)
    • Place of Presentation
      Yokohama, Japan
    • Year and Date
      20111100
  • [Presentation] Regioselective Carbonylation of Unactivated C(sp^3)-H Bonds in Aliphatic Amides2011

    • Author(s)
      Chatani, N
    • Organizer
      15th Japan-Korea Joint Seminar on Organic Chemistry
    • Place of Presentation
      Gyeongju, Korea
    • Year and Date
      20110900
  • [Presentation] Catalytic Transformations Involving Activation of C-H Bonds2011

    • Author(s)
      Chatani, N
    • Organizer
      4th Aachen-Osaka Joint Symposium
    • Place of Presentation
      Aachen, Germany
    • Year and Date
      20110900
  • [Presentation] Catalytic Transformations Involving Activation of Unreactive Bonds2010

    • Author(s)
      Chatani, N
    • Organizer
      3rd Peking University-Elli Lilly Symposium
    • Place of Presentation
      Beijing, China
    • Year and Date
      2010-10-26

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Published: 2015-07-16  

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