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2006 Fiscal Year Final Research Report Summary

Development of Highly Efficient Synthetic Reactions by Controlling Electron-Transfer Processes with a Combination of Different Metals

Research Project

Project/Area Number 16350057
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionOKYAMA UNIVERSITY

Principal Investigator

TAKAI Kazuhiko  Okayama University, Graduate School of Natural Science and Technology, Division of Chemistry and Biochemistry, Professor, 大学院自然科学研究科, 教授 (00144329)

Co-Investigator(Kenkyū-buntansha) OSHIKI Toshiyuki  Okayama University, Graduate School of Natural Science and Technology, Division of Chemistry and Biochemistry, Lecturer, 大学院自然科学研究科, 講師 (80311794)
KUNINOBU Yoichiro  Okayama University, Graduate School of Natural Science and Technology, Division of Chemistry and Biochemistry, Assistant Professor, 大学院自然科学研究科, 助手 (40372685)
Project Period (FY) 2004 – 2006
KeywordsElectron Transfer / Low-valent Metal / Zinc / Chromium / Nickel / Tantalum-Alkyne Complex / Rhenium Catalyst / C-H Bond Activation
Research Abstract

The following stereoselective reactions are developed by controlling electron-transfer processes. (1) Cross-Coupling Reactions of Alkynes and Aldehydes Leading to Allylic Alcohols by a Combination of Chromium(II), a Catalytic Amount of Nickel(II), and Water. (2) Preparation of Cyclopropylsilanes from Terminal Alkenes with Organochromium Reagents. (3) Transformation of Aldehydes into (E)-1-Alkenylsilanes and (E)-1-Alkenylboronic Esters with a Catalytic Amount of a Chromium Salt and Zinc (or Manganese). (4) Mechanistic Study of Ligand Exchange Reactions of η^-TaCl_3(Me_3SiC=CSiMe_3)(dme) with Internal Alkynes. (5) Cyclotrimerization of Terminal Alkynes with a Catalytic Amount of η^2-TaCl_3(Me_3SiC=CSiMe_3)(dme).
In addition, we developed novel organic reactions based on carbon-hydrogen bond activation with rhenium catalysts : (6) Rhenium-Catalyzed Formation of Indene Frameworks via C-H Bond Activation from Aromatic Aldimines and Acetylenes ; (7) Insertion of Polar Unsaturated Molecules into Carbon-Rhenium Bonds Generated by C-H Bond Activation: Synthesis of Isobenzofuran and Phthalimidine Derivatives ; (8) Rhenium-and Aniline-Catalyzed One-Pot Annulation of Aromatic Ketones and α,β-Unsaturated Esters Initiated by C-H Bond Activation.

  • Research Products

    (40 results)

All 2007 2006 2005 2004

All Journal Article (34 results) Book (5 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Insertion of Polar and Nonpolar Unsaturated Molecules into Carbon-Rhenium Bonds Generated by C-H Bond Activation : Synthesis of Phthalimidine and Indene Derivatives.2006

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

      J. Am. Chem. Soc. 128巻,1号

      Pages: 202-209

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Isocyanate Acting as a Carbonyl Precursor : Pyridyl Group-Assisted Formation of 4H-Pyrido[1,2-a]pyrimidin-4-ones from Ketimines and Isocyanates.2006

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

      Biomol. Org. Chem. 4巻,2号

      Pages: 203-205

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Rhenium- and Aniline-Catalyzed One-Pot Annulation of Aromatic Ketones and α,β-Unsaturated Esters Initiated by C-H Bond Activation.2006

    • Author(s)
      Y.Kuninobu, Y.Nishina, M.Shouho, K.Takai
    • Journal Title

      Angew. Chem. Int. Ed. 45巻・17号

      Pages: 2766-2768

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Sequential Ruthenium-Catalyzed Hydroamination and Rhenium-Catalyzed C-H Bond Activation Leading to Indene Derivatives.2006

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

      Org. Lett. 8巻・13号

      Pages: 2891-2893

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Formal Hydrochromination of Alkynes under Nickel Catalysis. Regioselective Reductive Coupling of Alkynes and Aldehydes Leading to Allylic Alcohols.2006

    • Author(s)
      K.Takai, S.Sakamoto, T.Isshiki, T.Kokumai
    • Journal Title

      Tetrahedron 62巻・32号

      Pages: 7534-7539

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Efficient Catalytic Insertion of Acetylenes into a Carbon-Carbon Single Bond of Non-Strained Cyclic Compounds under Mild Conditions.2006

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

      J. Am. Chem. Soc. 128巻・35号

      Pages: 11368-11369

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Rhenium-Catalyzed Insertion of Aldehyde into a C-H Bond : Synthesis of Isobenzofuran Derivatives.2006

    • Author(s)
      Y.Kuninobu, Y.Nishina, C.Nakagawa, K.Takai
    • Journal Title

      J. Am. Chem. Soc. 128巻・38号

      Pages: 12376-12377

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Rhenium-Catalyzed Addition of Trimethylsilylacetylene to Aldimines.2006

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

      Chem. Lett. 35巻・12号

      Pages: 1376-1377

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Titanium and Zirconium Complexes with Non-Salicylaldimine-Type Imine Phenoxy Chelate Ligands : Syntheses, Structures, and Ethylene-Polymerization Behavior.2006

    • Author(s)
      Y.Suzuki, H.Tanaka, T.Oshiki, K.Takai, T.Fujita
    • Journal Title

      Chem. Asian J. 1巻・6号

      Pages: 878-887

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Insertion of Polar and Nonpolar Unsaturated Molecules into Carbon-Rhenium Bonds Generated by C-H Bond Activation : Synthesis of Phthalimidine and Indene Derivatives2006

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

      J.Am.Chem.Soc. 28(1)

      Pages: 202-209

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Isocyanate Acting as a Carbonyl Precursor : Pyridyl Group-Assisted Formation of 4H-Pyrido[1,2-a]pyrimidin-4-ones from Ketimines and Isocyanates.2006

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

      Org.Biomol.Chem. 4(2)

      Pages: 203-205

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Rhenium-and Aniline-Catalyzed One-Pot Annulation of Aromatic Ketones and α,β-Unsaturated Esters Initiated by C-H Bond Activation.2006

    • Author(s)
      Kuninobu Y., Nishina Y., Shouho M., Takai K.
    • Journal Title

      Angew.Chem.Int.Ed. 45(17)

      Pages: 2766-2768

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Sequential Ruthenium-Catalyzed Hydroamination and Rhenium-Catalyzed C-H Bond Activation Leading to Indene Derivatives.2006

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

      Org.Lett. 8(13)

      Pages: 2891-2893

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Formal Hydrochromination of Alkynes under Nickel Catalysis. Regioselective Reductive Coupling of Alkynes and Aldehydes Leading to Allylic Alcohols.2006

    • Author(s)
      Takai K., Sakamoto S., Isshiki T., Kokumai T.
    • Journal Title

      Tetrahedron 62(32)

      Pages: 7534-7539

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Efficient Catalytic Insertion of Acetylenes into a Carbon-Carbon Single Bond of Non-Strained Cyclic Compounds under Mild Conditions.2006

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

      J.Am.Chem.Soc. 128(35)

      Pages: 11368-11369

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Rhenium-Catalyzed Insertion of Aldehyde into a C-H Bond : Synthesis of Isobenzofuran Derivatives.2006

    • Author(s)
      Kuninobu Y., Nishina Y., Nakagawa C., Takai K.
    • Journal Title

      J.Am.Chem.Soc. 128(38)

      Pages: 12376-12377

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Rhenium-Catalyzed Addition of Trimethylsilylacetylene to Aldimines.2006

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

      Chem.Lett. 35(12)

      Pages: 1376-1377

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Titanium and Zirconium Complexes with Non-Salicylaldimine-Type Imine Phenoxy Chelate Ligands : Syntheses, Structures, and Ethylene-Polymerization Behavior.2006

    • Author(s)
      Suzuki Y., Tanaka H., Oshiki T., Takai K., Fujita T.
    • Journal Title

      Chem.Asian J. 1(6)

      Pages: 878-887

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Rhenium-Catalyzed Formation of Indene Frameworks via C-H Bond Activation : [3+2] Annulation of Aromatic Aldimines and Acetylenes.2005

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

      J. Am. Chem. Soc. 127巻,39号

      Pages: 13498-13499

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis of Bis(phenoxyimine) Ti Alkyl Complexes and Observation of Living Species by 1^H NMR Spectroscopy.2005

    • Author(s)
      H.Makio, T.Oshiki, K.Takai, T.Fujita
    • Journal Title

      Chem. Lett. 34巻,10号

      Pages: 1382-1383

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] A Novel Heteroligated Phenoxy-Based Titanium Complex : Structure, Stability, and Ethylene Polymerization Behavior.2005

    • Author(s)
      Y.Suzuki, T.Oshiki, H.Tanaka, K.Takai, T.Fujita
    • Journal Title

      Chem. Lett. 34巻,10号

      Pages: 1458-1459

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Rhenium-Catalyzed Insertion of Terminal Acetylenes into a C-H Bond of Active Methylene Compounds.2005

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

      Org. Lett. 7巻,22号

      Pages: 4823-4825

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Dramatic Rate Acceleration by a Dipheny1-2-pyridylphosphine Ligand in the Hydration of Nitriles Catalyzed by Ru(acac)_2 Complexes.2005

    • Author(s)
      T.Oshiki, H.Yamashita, K.Sawada, M.Utsunomiya, K.Takahashi, K.Takai
    • Journal Title

      Organometallics 24巻,26号

      Pages: 6287-6290

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Rhenium-Catalyzed Formation of Indene Frameworks via C-H Bond Activation : [3+2] Annulation of Aromatic Aldimines and Acetylenes.2005

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

      J.Am.Chem.Soc. 27(39)

      Pages: 13498-13499

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Rhenium-Catalyzed Insertion of Terminal Acetylenes into a C-H Bond of Active Methylene Compounds.2005

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

      Org.Lett. 7(22)

      Pages: 4823-4825

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis of Bis(phenoxyimine) Ti Alkyl Complexes and Observation of Living Species by ^1H NMR Spectroscopy.2005

    • Author(s)
      Makio H., Oshiki T., Takai K., Fujita T.
    • Journal Title

      Chem. Lett. 34(10)

      Pages: 1382-1383

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] A Novel Heteroligated Phenoxy-Based Titanium Complex : Structure, Stability, and Ethylene Polymerization Behavior.2005

    • Author(s)
      Suzuki Y., Oshiki T., Tanaka H., Takai K., Fujita, T.
    • Journal Title

      Chem.Lett. 34(10)

      Pages: 1458-1459

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Dramatic Rate Acceleration by a Diphenyl-2-pyridyl- phosphine Ligand in the Hydration of Nitriles Catalyzed by Ru(acac)_2 Complexes2005

    • Author(s)
      Oshiki T., Yamashita H., Sawada K., Utsunomiya M., Takahashi K., Takai K.
    • Journal Title

      Organometallics 24(26)

      Pages: 6287-6290

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Catalytic Performance of Tantalum-η^2-Alkyne Complexes TaCl_3(R^1C=CR^2)L_2 for Alkyne Cyclotrimerization2004

    • Author(s)
      T.Oshiki, H.Nomoto, K.Tanaka, K.Takai
    • Journal Title

      Bull. Chem. Soc. Jpn. 77巻55号

      Pages: 1009-1011

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Preparation of Cyclopropylsilanes from Terminal Alkenes with Organochromium Reagents2004

    • Author(s)
      K.Takai, M.Hirano, S.Toshikawa
    • Journal Title

      Synlett 8号

      Pages: 1347-1350

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Transformation of Aldehydes into (E)-1-Alkenylsilanes and (E)-1- Alkenylboronic Esters with a Catalytic Amount of a Chromium Salt.2004

    • Author(s)
      K.Takai, Y.Kunisada, Y.Tachibana, N.Yamaji, E.Nakatani
    • Journal Title

      Bull. Chem. Soc. Jpn. 77巻8号

      Pages: 1581-1586

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Catalytic Performance of Tantalum-η^2-Alkyne Complexes [TaC_13(R^1C=CR^2)L_2] for Alkyne Cyclotrimerization.2004

    • Author(s)
      Oshiki T., Nomoto H., Tanaka K., Takai K.
    • Journal Title

      Bull.Chem.Soc.Jpn. 77(5)

      Pages: 1009-1011

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Preparation of Cyclopropylsilanes from Terminal Alkenes with Organochromium Reagents.2004

    • Author(s)
      Takai K., Hirano M., Toshikawa S.
    • Journal Title

      Synlett (8)

      Pages: 1347-1350

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Transformation of Aldehydes into (£)-l-Alkenylsilanes and (E)-1-Alkenylboronic Esters with a Catalytic Amount of a Chromium Salt.2004

    • Author(s)
      Takai K., Kunisada Y., Tachibana Y., Yamaji N., Nakatani E.
    • Journal Title

      Bull.Chem.Soc.Jpn. 77(8)

      Pages: 1581-1586

    • Description
      「研究成果報告書概要(欧文)」より
  • [Book] Comprehensive Organometallic Chemistry Ill Vol. 11 (Chapter 11.02 : Reductive Coupling Reactions Promoted by Low-Valent Early Transition Metals and Lanthanoids.)2007

    • Author(s)
      K.Takai
    • Total Pages
      39-73, 35
    • Publisher
      Elsevier Ltd.
    • Description
      「研究成果報告書概要(和文)」より
  • [Book] 実力養成化学スクール6「有機合成化学」,オレフィンを自在につくる,分担(6章, 115-137頁)2005

    • Author(s)
      高井和彦
    • Total Pages
      23
    • Publisher
      丸善(日本化学会編)
    • Description
      「研究成果報告書概要(和文)」より
  • [Book] Organic Reaction vol. 64 (Chapter 2 : Addition of Organochromium to Carbonyl Compounds)2004

    • Author(s)
      K.Takai
    • Total Pages
      253-612, 360
    • Publisher
      John Wiley and Sons, Inc.
    • Description
      「研究成果報告書概要(和文)」より
  • [Book] 第5版実験化学講座21巻「有機遷移金属化合物・超分子錯体」,有機クロム錯体,分担(5.1節, 109-123頁)2004

    • Author(s)
      高井和彦
    • Total Pages
      15
    • Publisher
      丸善(日本化学会編)
    • Description
      「研究成果報告書概要(和文)」より
  • [Book] 第5版実験化学講座18巻「有機化合物の合成VI金属を用いる有機合成」,クロムを用いる有機合成反応,分担(2.12節, 266-274頁)2004

    • Author(s)
      高井和彦
    • Total Pages
      9
    • Publisher
      丸善(日本化学会編)
    • Description
      「研究成果報告書概要(和文)」より
  • [Patent(Industrial Property Rights)] 複素環式化合物の製造方法2006

    • Inventor(s)
      高井和彦, 國信洋一郎
    • Industrial Property Rights Holder
      岡山大学
    • Industrial Property Number
      特願2006-66594
    • Filing Date
      2006-03-10
    • Description
      「研究成果報告書概要(和文)」より

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Published: 2008-05-27  

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