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Catalysis of Reactive Organometallics

Research Project

Project/Area Number 05236106
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Research InstitutionWaseda University

Principal Investigator

YAMAMOTO Akio  Waseda University, School of Science and Engineering, Professor, 理工学部, 教授 (30016711)

Co-Investigator(Kenkyū-buntansha) TAMARU Yoshinao  Nagasaki University, Faculty of Engineering, Professor, 工学部, 教授 (80026319)
TAKAYA Hidemasa  Kyoto University, Graduate School of Engineering, Professor, 大学院・工学研究科, 教授 (40022644)
SONOGASHIRA Kenkichi  Fukui University of Technology, Faculty of Engineering, Professor, 教授 (30029847)
KOMIYA Sanshiro  Tokyo University of Agriculture and Technology, Faculty of Technology, Professor, 工学部, 教授 (00111667)
ITO Yoshihiko  Kyoto University, Graduate School of Engineering, Professor, 大学院・工学研究科, 教授 (40026018)
野崎 京子  京都大学, 大学院・工学研究科, 助手 (60222197)
Project Period (FY) 1993 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥68,800,000 (Direct Cost: ¥68,800,000)
Fiscal Year 1995: ¥23,400,000 (Direct Cost: ¥23,400,000)
Fiscal Year 1994: ¥23,400,000 (Direct Cost: ¥23,400,000)
Fiscal Year 1993: ¥22,000,000 (Direct Cost: ¥22,000,000)
KeywordsOrganometallic compounds / Catalysis / Palladium / Asymmetric synthesis / Olefin / Ligand / ルテニウム / 白金 / 一酸化炭素 / カルボニル化 / ロジウム
Research Abstract

For developing novel catalytic processes various organotransition metal complexes have been prepared as models of catalytically active species and their properties relevant to elementary processes in catalytic reactions have been studied. (1) Various new organopalladium and ruthenium complexes of neutral and cationic nature have been prepared and their reactivities toward olefins, carbon monoxide, imines, and isocyanides have been examined. (2) Novel types of optically active, spiral-like polymers have been prepared and their properties showing the liquid crystal behavior have been examined. (3) As a model of ruthenium-catalyzed Michael type C-C bond forming catalysis new organoruthenium complexes have been prepared and their properties have been studied. (4) New organoplatinum complexes having ferrocenyl ligands have been synthesized. (5) Novel process of copolymerizing carbon monoxide and propylene to give isotactic polyketones has been discovered. (6) A new palladium-catalyzed process for converting alkynyl esters into unsaturated alcohols in combination with organozinc compounds has been realized.

Report

(4 results)
  • 1996 Final Research Report Summary
  • 1995 Annual Research Report
  • 1994 Annual Research Report
  • 1993 Annual Research Report
  • Research Products

    (56 results)

All Other

All Publications (56 results)

  • [Publications] A.Yamamoto: "Activation of C-O and C-N Bondsin Allylic Alchols and Amines by Palladium Complexes Promoted by CO_2.Synthetic Application to Allylation of Nucleophiles,Carbonylation,and Allylamine" Bull.Chem.Soc.Jpn.69. 1065-1078 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Y.Ito: "New Synthesis of(E)-Allylsilanes with High Enantiopurity Via Diastereoselective Intramolecular Bis-Silylation of Chiral Allylic Alcohols" J.Am.Chem.Soc.118. 3061-3062 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Komiya: "Synthesis and Reactivity of Organoplatinum-rhenium Heterobimetallic Complexes Having Sulfur Ligands" J.Mol.Cat.107. 323-328 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Sonogashira: "Reactions of σ-Ferrocenylplatinum Complexes with Carbon Monoxide and Isocyanide" J.Organometal.Chem.511. 47-57 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Takaya: "Palladium-Catalyzed Acylcyanation of Terminal Arylacetylenes.Synthesis of 1,3-Diaryl-3-cyano-2-propen-1-ones and Tetrasubstituted Furans" Bull.Chem.Soc.Jpn.69. 1629-1637 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Y.Tamaru: "Propargylation of Carbonyl Compounds via Umpolung of Propargylpalladium with Diethylzinc" Angew.Chem.,Int.Ed.Engl.35. 878-880 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Yamamoto: "Activation of C-O and C-N Bonds in Allylic Alchols and Amines by Palladium Complexes Promoted by CO_2. Synthetic Application to Allylation of Nucleophiles, Carbonylation, and Allylamine Disproportionation" Bull.Chem.Soc.Jpn.69. 1065-1078 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Y.Ito: "New Synthesis of (E) -Allylsilanes with High Enantiopurity via Diastereoselective Intramolecular Bis-Silylation of Chiral Allylic Alcohols" J.Am.Chem.Soc.118. 3061-3062 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Komiya: "Synthesis and Reactivity of Organoplatinum-rhenium Heterobimetallic Complexes Having Sulfur Ligands" J.Mol.Cat.107. 323-328 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Sonogashira: "Reactions of sigma-Ferrocenylplatinum Complexes with Carbon Monoxide and Isocyanide" J.Organometal.Chem.511. 47-57 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Takaya: "Palladium-Catalyzed Acylcyanation of Terminal Arylacetylenes. Synthesis of 1,3-Diaryl-3-cyano-2-propen-1-ones and Tetrasubstituted Furans" Bull.Chem.Soc.Jpn.69. 1629-1637 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Y.Tamaru: "Propargylation of Carbonyl Compounds via Umpolung of Propargylpalladium with Diethylzinc" Angew.Chem.Int.Ed.Engl.35. 878-880 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Yamamoto: "Activation of C-O and C-N Bonds in Allylic Alcohols and Amines by Palladium Complexes Promoted by CO_2. Synthetic Applications to Allylation of Nucleophiles, Carbonylation, and Allylamine Disproportionation." Bull. Chem. Soc. Jpn.(in press). (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] Y. Ito: "New Synthesis of Quinoxaline Derivatives Based on Palladium Catalyzed Oligomerization of 1,2-Diisocyanoarenes." Heterocycles,. 42. 597-615 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] K. Sonogashira: "Reaction of 1,1'-Ferrocenediylbis [chloro{(1,2,5,6-η)-1,5-cyclooctadiene} -platinum] with Triarylphosphine and Molecular Oxygen." Angew. Chem. Int. Ed. Engl.34. 319-321 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] S. Komiya: "Synthesis and Reactivity of Organoplatinum-rhenium Heterobimetallic Complexes Having Sulfur Ligand." J. Mol. Catal.(in press). (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] K. Nozaki: "Asymmetric Hydroformylation of Conjugated Dienes Catalyzed by [(R)-2-diphenylphosphino-1, 1'-din aphthalen-2'-yl] [(S)-1, 1'-dinaphthalen-2, 2'-diyl] phosphite-rhodium (I)." Chem. Commun.155-156 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] Y. Tamaru: "π-アリルパラジウムとの反応における有機亜鉛の特異な反応挙動:カルボニル化による非対称ケトンの合成とπ-アリルパラジウムの極性転換反応" 有機合成化学協会誌. 53. 1102-1113 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Futoshi Kawataka: "Synthesis and Thermolysis Behavior of Monoethylpalladium Complexes,EtPd(X)(PMe3)2(X=Electronegative Ligands)" Organometallics. 13. 3517-3524 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Yoshihiko Kayaki: "Remarkable Rate Enhancement in CO Insertion into Pd-C Bond by Generating Cationic Organopalladium Complexes 〔PdR(s)L2〕+BF4-(R=Alky1 Group,s=Acctone,L=Phosphine Ligands)form Neutral Monoorganopalladium Complexes 〔PdR(X)L2〕(X=Halide)" Chem.Lett.2171-2174 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Thomas Rappert: "Synthesis of Cationic Imine- and Amine-Coordinated Hydridoruthenium Complexes Relevant to Reductive Amination" Chem.Lett.2211-2214 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Thomas Rappert: "Synthesis and Properties of Cationic Hydrido(tertiary phosphine)ruthenium(II)Complex" Organometallics. 13. 4984-4993 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Akio Yamamoto: "Palladium-Catalyzed Double and Single Carbonylation of Aryl Halides and Allylic Comounds" Bull.Chem.Soc.Jpn.68. 433-446 (1995)

    • Related Report
      1994 Annual Research Report
  • [Publications] Futoshi Kawataka: "Synthesis and Properties of Cationic Organopalladium Complexes.Remarkable Rate Enhancement in Olefin Insertion into Paladium-Aryl Bond by Generation of a Cationic Palladium Complex from trans-PdPh(Br)(PMe3)2" Bull.Chem.Soc.Jpn.68. 654-660 (1995)

    • Related Report
      1994 Annual Research Report
  • [Publications] K.Onitsuka: "Synthesis and Properties of Ferrocenylethynyl Transition Metal Complex of Platinum,Palladium and Nickel" Bull.Chem.Soc.Jpn.67. 2611-2613 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] K.Onitsuka: "Synthesis,and Molecular Structure and Reactions of a Novel μ-σ、π-Cyclopentadienediyl Platinum-Manganese Complex" Chem.Lett. 2067-2070 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] K.Onitsuka: "Synthesis and Structure of Novel Metallacycle Complexes of Ruthenium Derived from 1,1'-Dialkynylferrocene" Chem.Lett. 2276-2282 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] T.Yoshida: "Reaction of 1,1'-Ferrocenediylbis〔chloro-{(1,2,5,6-η)-1,5-cyclolctadiene}plantinum〕with Triarvlphosphane and Molecular Oxygen" Angew.Chem.Int.Ed.Engl.34. 319-321 (1995)

    • Related Report
      1994 Annual Research Report
  • [Publications] K.Onitsuka: "Insertion reaction of isocyanide into the Pt-C bonds of 2,5-thicnylene-bridged diplatium complexes and 2-thienyl platinum complexes:molecular structure of Cl(Et_3P)_2PtC=(NC_6H_4OMe-p)C_4H_2SC=(NC_6H_4OMe-p)Pt(PEt_3)_2ClCH_2Cl_2" J.Organomet.Chem. (in press). (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] K.Onitsuka: "C-H Bond Activation of the Ferrocenyl Group in the Reaction of σ-Ferrocenylplatinum Complex with Dimethyl Acetylenedicarboxylate" Chem.Lett. (in press). (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Komiya: "C-O Bond Cleavage and Oxidative Addition of Allyl Carboxylate to Ruthenium(O).Isolation of (π-allyl)(trifluoroacetato)tris(triethylphosphine)rutheium(II)" J.Organometa.Chem. 471. C6-C7 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] A.Fukuoka: "Synthesis and Structure of Heterodinuclear Platimum-Tungsten and-Molybdenum Complexes with Alkyl and Ligands:A Mechanistic Study of the Migration of Alkyl and Groups from Platinum to Tungsten and Molybdenum" Organometallics. 13. 4033-4044 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Komiya: "Synthesis and Structure of a Carbon Dioxide Complex of Iron(O)Containing 1,2-Bis(diethylphosphino)ethane Ligands" J.Chem.Soc.,Chem.Commun.1114-1116 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] A.Fukuoka: "Synthesis and Structure of Novel Organo(siloxo)platimum Complexes.Facile Reduction by Dihydrogen." Chem.Lett.1641-1644 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] T.Sone: "Synthesis,Structure and Reactivities of cis-Dimethyl(ηl-allyl)gold(III)Complexes." Bull.Chem.Jpn. (in press).

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Komiya: "Organometallic Dinuclear Complexes of Transition Metals.Alkyl Transfer from Platinum,Palladium and Gold to Transition Metals" Trends in Organometallic Chemistry. (in press).

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Suginome: "Syntheses and Interconvertion of 〔Bis(silyl)alkene〕palladium(O)and Bis(silyl)palladium(II)Complex:A Mechanistic Model for Palladium-Catalyzed Bis(silylation)" Organometallics. 13. 2900-2902 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Suginome: "Novel Activation of Two Si-Si s-Bonds in a Molecule by tert-Alkyl Isocyanide-Palladium Complex" Organometallics. 13. 4148-4150 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Hada: "Palladium-Catalyzed Intermolecular Cyanosilylation of Alkynes Leading to Stereoselective Syntheses of α,β-Unsaturated Nitriles" Tetrahedron Lett.35. 8635-8638 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Hada: "Theoretical Study on the Reaction Mechanism and Redioselectivity of Silastannation of Acetvlenes with a Palladium Catalvst" J.Am.Chem.Soc.116. 8754-8765 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] K.Nozaki: "A Chiral Bimetallic Lewis Acid:A Cooperative Binding of Two Amine Molecules to a Chiral Diboronic Ester." Angew.Chem,Int.Ed.Engl.33. 2452-2454 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] K.Nozaki: "Acylcyanation of Terminal Acetylenes:Palladium Catalyzed Addition of Aryloyl Cyanides to Aryl acetylenes" J.Org.Chem.59. 2679-2681 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] K.Mashima: "Cationic BINAP-Ru(II)Halide Complexes:Highly Efficient Catalysts for Strereoselective Asymmetric Hydrogenation of a-and β-Functionalized Ketones" J.Org.Chem.59. 3064-3076 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] X.Zhang: "Enatioselective Hydrogenation of Acyclic Aromatic Ketones Catalyzed by BINAP-Ir(I)-Aminophosphine Systems" Tetrahedron Asymmetry. 5. 1179-1182 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] R.Yamaguchi: "Facile Introduction of Michael Acceptors into Nitrogen Heterocycles.A New Efficient Route to Fused α-Methylene-γ-lactams" Chem.Lett.1809-1812 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] X.Zhang: "Highly Enantioselective Hydrogenation of α、β-Unsaturated Carboxylic Acids Catalyzed by H8-BINAP-Ru(II)Complexes" Synlett. 501-503 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] K.Ono: "Palladium Catalyzed Arylation of N-Alkyl 0-Aryl Carbamates:Synthesis of Cinnamyl Alcohols via Heck Arylation" Tetrahedron Lett.35. 4133-4136 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Y.Tamaru: "Highly Regio-and Strereoselective Diels-Alder Reaction of Monothiomaleimide,an Ambident C=S and C=C Dienophile" J.Chem.Soc.,Chem,Commun.2365-2366 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Kimura: "Palladium(2+)catalyzed 5-Endo-Trigonal Cyclization of 2-Hydroxy-3-butenylamines:Synthesis of Five-Membered Nitrogen Heterocycles" J.Chem.Soc.,Chem,Commun.2531-2533 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Y.Tamaru: "Convenient Synthesis of 4-Methylene-1,3-oxazolidin-2-ones and 4-Methylene-1,3-oxazin-2-ones via Transition-metal Catalyzed Intramolecular Addition of Nitrogen Atom to Acetylenic Triple Bond" Bull.Chem.Soc.Jpn.67. 2838-2849 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Kimura: "Silver(I)Catalyzed Aminocylization of 2,3-Butadienyl and 3,4-Pentadienyl Carbamates:An Efficient and Stereoselective Synthesis of 4-Vinyl-2-oxazolidinones and 4-Vinyltetrahydro-1,3-oxazin-2-ones" Bull.Chem.Soc.Jpn.(in press).

    • Related Report
      1994 Annual Research Report
  • [Publications] Y.Tamura: "Highly Stereoselective Allylation of Aldehyde:Generation of Stereochemically Defined Allylzinc Species via Alky-Allyl Exchange Reaction between π-Allylpalladium and Diethylzinc" Bull.Chem.Soc.Jpn.(in press).

    • Related Report
      1994 Annual Research Report
  • [Publications] Isao Shimizu: "Palladium-Catalyzed Reactions of Alkenyloxiranes with Carbon Monoxides" Tetrahedron Lett.,34. 13. 2135-2138 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Radhey S.Srivastava: "Synthesis,characterization,and carbonylation reactions of methylpalladium amide,carbamate,and alkyl carbonate complexes" J.Organomet.Chem.,451. 221-229 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Yoo-Joo Kim: "Preparation and properties of alkyl palladium(II) and -platinum(II) alkynyl complexes" Chem.Lett.247-250 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Masato Sakamoto: "Synthesis of the First Carbon Dioxide Coordinated Palladium(0) complexes,Pd(eta^2-CO_2)(PMePh_2)_2" Organometallics,13. 407-409 (1994)

    • Related Report
      1993 Annual Research Report

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Published: 1993-04-01   Modified: 2016-04-21  

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