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2011 Fiscal Year Final Research Report

Development of Novel Transformations via Cleavage of Inactive Bonds using Group 7 Transition Metal Catalysts

Research Project

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Project/Area Number 21750103
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionOkayama University

Principal Investigator

KUNINOBU Yoichiro  岡山大学, 大学院・自然科学研究科, 助教 (40372685)

Project Period (FY) 2009 – 2011
Keywordsレニウム / マンガン / C-H結合活性化 / C-C結合切断 / 挿入 / 付加 / 位置選択的 / 触媒反応
Research Abstract

We focused on group 7 transition metal compounds, such as rhenium and manganese complexes, and carried out investigations to develop novel and efficient transformations using such complexes as catalysts. As a result, we have succeeded in the development of transformations via the cleavage of C-H or C-C bond, which forms skeletons of organic molecules and is difficult to be cleaved. In addition, we also developed regioselective cycloaddition reactions.

  • Research Products

    (49 results)

All 2012 2011 2010 2009 Other

All Journal Article (26 results) (of which Peer Reviewed: 26 results) Presentation (19 results) Book (1 results) Remarks (1 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Manganese-Catalyzed Cleavage of a Carbon-Carbon Single Bond between Carbonyl and Alpha Carbon Atoms of Ketones.2011

    • Author(s)
      Kuninobu, Y.; Uesugi, T.; Kawata, A.; Takai, K
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 50 Pages: 10406-10408

    • Peer Reviewed
  • [Journal Article] Synthesis of Multisubstituted Cyclopentadienes from Cyclopentenones Prepared via Catalytic Double Aldol Condensation and Nazarov Reaction Sequence2011

    • Author(s)
      Nishina, Y.; Tatsuzaki, T.; Tsubakihara, A.; Kuninobu, Y.; Takai, K
    • Journal Title

      Synlett

      Pages: 2585-2589

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Allylation of C-H Bonds of Benzoic and Acrylic Acids2011

    • Author(s)
      Kuninobu, Y.; Ohta, K.; Takai, K
    • Journal Title

      Chem. Commun

      Pages: 10791-10793

    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Synthesis of Dibenzophosphole Oxides via Intramolecular Dehydrogenative Cyclization2011

    • Author(s)
      Kuninobu, Y.; Yoshida, T.; Takai, K
    • Journal Title

      J. Org. Chem

      Volume: 76 Pages: 7370-7376

    • Peer Reviewed
  • [Journal Article] Synthesis of meso-Substituted Tetraarylalkynylporphyrins via Rhenium-Catalyzed Formation of Naphthalene Units2011

    • Author(s)
      Samarat, A.; Kuninobu, Y.; Takai, K
    • Journal Title

      Synlett

      Pages: 2177-2180

    • Peer Reviewed
  • [Journal Article] Indium-Catalyzed Construction of Polycyclic Aromatic Hydrocarbon Skeletons via Dehydration2011

    • Author(s)
      Kuninobu, Y.; Tatsuzaki, T.; Matsuki, T.; Takai, K
    • Journal Title

      J. Org. Chem

      Volume: 76 Pages: 7005-7009

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Regio-and Stereoselective Addition of Two Carbon Units to Terminal Alkynes via Carbon-Carbon Bond Cleavage ofβ-Keto Sulfones2011

    • Author(s)
      Kuninobu, Y.; Matsuzaki, H.; Nishi, M.; Takai, K
    • Journal Title

      Org. Lett

      Volume: 13 Pages: 2959-2961

    • Peer Reviewed
  • [Journal Article] Organic Reactions Catalyzed by Rhenium Carbonyl Complexes2011

    • Author(s)
      Kuninobu, Y.; Takai, K
    • Journal Title

      Chem. Rev

      Volume: 111 Pages: 1938-1953

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Insertion of Terminal Alkenes into a C(sp^2)-H Bond and Successive Transfer Hydrogenation2011

    • Author(s)
      Kuninobu, Y.; Nakahara, T.; Yu, P.; Takai, K
    • Journal Title

      J. Organomet. Chem

      Volume: 696 Pages: 348-351

    • Peer Reviewed
  • [Journal Article] Cross-Coupling Reactions between C(sp^2)-H and C(sp^3)-H Bonds via Sequential Dehydrogenation and C-H Insertion2010

    • Author(s)
      Kuninobu, Y.; Asanoma, D.; Takai, K
    • Journal Title

      Synlett

      Pages: 2883-2886

    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Synthesis of Glycine Derivatives via Carbon-Nitrogen Bond Cleavage Using Diazoacetate2010

    • Author(s)
      Kuninobu, Y.; Nishi, M.; Takai, K
    • Journal Title

      Chem. Commun

      Volume: 46 Pages: 8860-8862

    • Peer Reviewed
  • [Journal Article] Synthesis of Functionalized Pentacenes from Isobenzofurans Derived from C-H Bond Activation2010

    • Author(s)
      Kuninobu, Y.; Seiki, T.; Kanamaru, S.; Nishina, Y.; Takai, K
    • Journal Title

      Org. Lett

      Volume: 12 Pages: 5287-5289

    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Synthesis of Silafluorene Derivatives via Cleavage of Silicon-Hydrogen and Carbon-Hydrogen Bonds2010

    • Author(s)
      Ureshino, T.; Yoshida, T.; Kuninobu, Y.; Takai, K
    • Journal Title

      J. Am. Chem. Soc

      Volume: 132 Pages: 14324-14326

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Diastereoselective Synthesis of Aminoindanes via the Insertion of Allenes into a C-H Bond2010

    • Author(s)
      Kuninobu, Y.; Yu, P.; Takai, K
    • Journal Title

      Org. Lett

      Volume: 12 Pages: 4274-4276

    • Peer Reviewed
  • [Journal Article] Regioselective Functionalization of Alkanes by Sequential Dehydrogenation-Hydrozirconation2010

    • Author(s)
      Kuninobu, Y.; Ureshino, T.; Yamamoto, S.-i.; Takai, K
    • Journal Title

      Chem. Commun

      Volume: 46 Pages: 5310-5312

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Regioselective Synthesis of Phenol Derivatives from 1, 3-Diesters and Terminal Alkynes2010

    • Author(s)
      Kuninobu, Y.; Iwanaga, T.; Nishi, M.; Takai, K
    • Journal Title

      Chem. Lett

      Volume: 39 Pages: 894-895

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Synthesis of Indenones by Novel Dehydrative Trimerization of Aryl Aldehydes via C-H Bond Activation2010

    • Author(s)
      Kuninobu, Y.; Matsuki, T.; Takai, K
    • Journal Title

      Org. Lett

      Volume: 12 Pages: 2948-2950

    • Peer Reviewed
  • [Journal Article] Rhenium-and Manganese-Catalyzed Carbon-Carbon Bond Formation Using 1, 3-Dicarbonyl Compounds and Alkynes2010

    • Author(s)
      Kuninobu, Y.; Kawata A.; Yudha, S. S.; Takata, H.; Nishi, M.; Takai, K
    • Journal Title

      Pure Appl. Chem

      Volume: 82 Pages: 1491-1501

    • Peer Reviewed
  • [Journal Article] Indium-Catalyzed Synthesis of Keto Esters from Cyclic 1, 3-Diketones and Alcohols and Application to the Synthesis of Seratrodast2010

    • Author(s)
      Kuninobu, Y.; Kawata, A.; Noborio, T.; Yamamoto, S.-i.; Matsuki, T.; Takata, K., Takai, K
    • Journal Title

      Chem. Asian J

      Volume: 5 Pages: 941-945

    • Peer Reviewed
  • [Journal Article] Rhenium-and Manganese-Catalyzed Synthesis of Aromatic Compounds from 1, 3-Dicarbonyl Compounds and Alkynes2010

    • Author(s)
      Kuninobu, Y.; Nishi, M.; Kawata A.; Takata, H.; Hanatani, Y.; Yudha, S. S.; Iwai, A.; Takai, K
    • Journal Title

      J. Org. Chem

      Volume: 75 Pages: 334-341

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Addition ofβ-Enamino Esters to Allenes2009

    • Author(s)
      Kuninobu, Y.; Yamashita, A.; Yamamoto, S.-i.; Yudha S. S.; Takai, K
    • Journal Title

      Synlett

      Pages: 3027-3031

    • Peer Reviewed
  • [Journal Article] Rhenium-and Manganese-Catalyzed Insertion of Alkynes into a Carbon-Carbon Single Bond of Cyclic and Acyclic 1, 3-Dicarbonyl Compounds2009

    • Author(s)
      Kuninobu, Y.; Kawata, A.; Nishi, M.; Yudha S. S., Chen, J.; Takai, K
    • Journal Title

      Chem. Asian J

      Volume: 4 Pages: 1424-1433

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Regioselective Alkylation of Phenols2009

    • Author(s)
      Kuninobu, Y.; Matsuki, T.; Takai, K
    • Journal Title

      J. Am. Chem. Soc

      Volume: 131 Pages: 9914-9915

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Regio-and Stereoselective Dimerization and Cyclotrimerization of Terminal Alkynes2009

    • Author(s)
      Kawata, A.; Kuninobu, Y.; Takai, K
    • Journal Title

      Chem. Lett

      Volume: 38 Pages: 836-837

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Insertion of Nonpolar and Polar Unsaturated Molecules into an Olefinic C-H Bond2009

    • Author(s)
      Kuninobu, Y.; Fujii, Y.; Matsuki, T.; Nishina, Y.; Takai, K
    • Journal Title

      Org. Lett

      Volume: 11 Pages: 2711-2714

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Formation of Bicyclo[3. 3. 1] nonene Frameworks by a Reaction of Cyclicβ-Keto Esters with Terminal Alkynes2009

    • Author(s)
      Kuninobu, Y.; Morita, A.; Mishi, M.; Kawata, A.; Takai, K
    • Journal Title

      Org. Lett

      Volume: 11 Pages: 2535-2537

    • Peer Reviewed
  • [Presentation] 遷移金属触媒による不活性結合の切断を伴うシラフルオレンおよびホスファフルオレン誘導体の合成2011

    • Author(s)
      國信洋一郎, 嬉野智也, 吉田卓矢, 高井和彦
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Year and Date
      20110907-09
  • [Presentation] レニウム触媒によるβ-ケトスルホン由来の二つの炭素ユニットの末端アルキンへの立体選択的付加反応2011

    • Author(s)
      西光海, 松崎大典, 國信洋一郎, 高井和彦
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Year and Date
      20110907-09
  • [Presentation] レニウム触媒による芳香族イミンC-H結合への末端アルケンの挿入とイミノ基還元反応2011

    • Author(s)
      中原崇博, 于鵬, 國信洋一郎, 高井和彦
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Year and Date
      20110907-09
  • [Presentation] Transition Metal-Catalyzed Dehydrogenative Synthesis of Silafluorene and Phosphafluorene Derivatives2011

    • Author(s)
      Yoichiro Kuninobu, Tomonari Ureshino, Takuya Yoshida, and Kazuhiko Takai
    • Organizer
      The 16th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis(OMCOS-16)
    • Place of Presentation
      Shanghai, China
    • Year and Date
      20110724-28
  • [Presentation] Indium-Catalyzed Retro-Claisen Rearrangement2010

    • Author(s)
      Shun-ichi Yamamoto, Atsushi Kawata, Taihei Noborio, Takashi Matsuki, Kazumi Takata, Yoichiro Kuninobu, and Kazuhiko Takai
    • Organizer
      The International Chemical Congress of Pacific Basin Societies(Pacifichem 2010)
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      20101215-20
  • [Presentation] Manganese-Catalyzed Regioselective Synthesis of Tetrasubstituted Benzenes fromβ-Keto Esters and Terminal Alkynes2010

    • Author(s)
      Mitsumi Nishi, Salprima Yudha S., Yoichiro Kuninobu, and Kazuhiko Takai
    • Organizer
      The International Chemical Congress of Pacific Basin Societies(Pacifichem 2010)
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      20101215-20
  • [Presentation] Rhenium-Catalyzed Regioselective Alkylation of Phenol Derivatives2010

    • Author(s)
      Yoichiro Kuninobu, Takashi Matsuki, and Kazuhiko Takai
    • Organizer
      The International Chemical Congress of Pacific Basin Societies(Pacifichem 2010)
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      20101215-20
  • [Presentation] 連続的な脱水素-ヒドロジルコニウム化反応を利用した飽和炭化水素の官能基化反応2010

    • Author(s)
      山本俊一, 嬉野智也, 國信洋一郎, 高井和彦
    • Organizer
      第57回有機金属化学討論会
    • Place of Presentation
      中央大学多摩キャンパス
    • Year and Date
      20100916-18
  • [Presentation] 鉄触媒を用いるN, N-ジメチルアニリン誘導体の炭素-窒素結合切断2010

    • Author(s)
      西光海, 國信洋一郎, 高井和彦
    • Organizer
      第57回有機金属化学討論会
    • Place of Presentation
      中央大学多摩キャンパス
    • Year and Date
      20100916-18
  • [Presentation] レニウム触媒を用いるC-H結合へのアレンの挿入反応によるジアステレオ選択的なアミノインダン誘導体の合成2010

    • Author(s)
      于鵬, 國信洋一郎, 高井和彦
    • Organizer
      第57回有機金属化学討論会
    • Place of Presentation
      中央大学多摩キャンパス
    • Year and Date
      20100916-18
  • [Presentation] Rhenium-Catalyzed Regioselective Alkylation of Phenols2010

    • Author(s)
      Yoichiro Kuninobu, Takashi Matsuki, and Kazuhiko Takai
    • Organizer
      XXIV International Conference on Organometallic Chemistry(ICOMC2010)
    • Place of Presentation
      Taipei, Taiwan
    • Year and Date
      20100718-23
  • [Presentation] Rhenium-Catalyzed Regioselective Alkylation of Phenols2009

    • Author(s)
      Takashi Matsuki, Yoichiro Kuninobu, Kazuhiko Takai
    • Organizer
      IKCOK-11
    • Place of Presentation
      Kyoto
    • Year and Date
      20091109-13
  • [Presentation] Rhenium-and Manganese-Catalyzed Construction of 2-Pyranones fromβ-Keto Esters and Alkynes2009

    • Author(s)
      Mitsumi Nishi, Atsushi Kawata, Hisatsugu Takata, Yoichiro Kuninobu, Kazuhiko Takai
    • Organizer
      IKCOK-11
    • Place of Presentation
      Kyoto
    • Year and Date
      20091109-13
  • [Presentation] Rhenium-Catalyzed Reactions of Active Methylene Compounds with Allenes2009

    • Author(s)
      Yoichiro Kuninobu, Salprima Yudha S., Atsuhiro Yamashita, Kazuhiko Takai
    • Organizer
      IKCOK-11
    • Place of Presentation
      Kyoto
    • Year and Date
      20091109-13
  • [Presentation] レニウムおよびマンガン触媒によるβ-ケトエステルとアルキンからの2-ピラノンの構築2009

    • Author(s)
      西光海, 川田篤志, 國信洋一郎, 高井和彦
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      京都
    • Year and Date
      20090909-11
  • [Presentation] レニウム触媒によるフェノールの位置選択的アルキル化反応2009

    • Author(s)
      松木崇, 國信洋一郎, 高井和彦
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      京都
    • Year and Date
      20090909-11
  • [Presentation] レニウム触媒による活性メチレン化合物とアレンとの反応2009

    • Author(s)
      國信洋一郎, ユダサルプリマ, 山下圧広, 高井和彦
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      京都
    • Year and Date
      20090909-11
  • [Presentation] Rhenium-and Manganese-Catalyzed Carbon-Carbon Bond Formation usingβ-Keto Esters2009

    • Author(s)
      Kazuhiko Takai, Yoichiro Kuninobu, Atsushi Kawata, Salprima Yudha S
    • Organizer
      OMCOS-15
    • Place of Presentation
      Glasgow
    • Year and Date
      20090726-30
  • [Presentation] Rhenium-Catalyzed Insertion of Unsaturated Molecules into an Olefinic C-H Bond and its Application to the Synthesis of Cp-Re Complexes2009

    • Author(s)
      Yoichiro Kuninobu, Takashi Matsuki, Yasuo Fujii, Yuta Nishina, Kazuhiko Takai
    • Organizer
      OMCOS-15
    • Place of Presentation
      Glasgow
    • Year and Date
      20090726-30
  • [Book] 使える!有機合成反応241実践ガイド2010

    • Author(s)
      國信洋一郎, 他
    • Total Pages
      70-71, 148-149, 426-427
    • Publisher
      化学同人
  • [Remarks]

    • URL

      http://achem.okayama-u.ac.jp/omc/index.html

  • [Patent(Industrial Property Rights)] 新規光学活性ホスフィン化合物、その製造法およびその用途2012

    • Inventor(s)
      國信洋一郎,折口和希,高井和彦
    • Industrial Property Rights Holder
      國信洋一郎,折口和希,高井和彦
    • Industrial Property Number
      特許、特願2012-051415
    • Filing Date
      2012-03-08
  • [Patent(Industrial Property Rights)] シラフルオレン誘導体の合成方法2010

    • Inventor(s)
      國信洋一郎,嬉野智也,高井和彦
    • Industrial Property Rights Holder
      國信洋一郎,嬉野智也,高井和彦
    • Industrial Property Number
      特許、特願2010-053857
    • Filing Date
      2010-03-10

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Published: 2013-07-31  

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