Metallocenes WILEY-VCH. Volume 2. Synthesis Reactivity Applications. Edited by Antonio Togni and Ronald L. Halterman
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1 Metallocenes Volume 2 Synthesis Reactivity Applications Edited by Antonio Togni and Ronald L. Halterman WILEY-VCH Weinheim New York Chichester Brisbane Singapore Toronto /
2 Preface V Volume 1 Synthesis and Reactivity 1 Main Group Metallocenes P. Jutzi and N. Burford 1.1 Abstract Introduction Synthetic Procedures Reactions Involving Cyclopentadienes Salt Metathesis Reactions Disproportionation, Comproportionation and Decomposition Halide Ion Abstraction Substitution onto the Cp Ligand Frame Reduction Addition of Cp Anions Characterization Features Structural Types Sandwich Complexes Half Sandwich Complexes /i-rc-cyclopentadienyl Molecular Complexes ju-rc-cyclopentadienyl Super-Sandwich Polymers Dimers Clusters Cp-Element Orbital Interactions Orbital Interaction Model for Half Sandwich Complexes Orbital Interaction Model for Sandwich Complexes Metallocenes of the Alkali Metals 23 /
3 VI Contents Monomers and Polymers Lithocene and Sodocene Anions Metallocenes of the Alkaline Earth Metals Beryllocene Alkaline Earth Sandwich Metallocenes Half Sandwich Metallocenes of the Group 2 Elements Metallocenes of the Group 13 Elements Half Sandwich Monomers, Dimers, Oligomers and Polymers Clusters Metallocenes Involving Group 13 Elements in Oxidation State in Heteroatom Clusters Metallocenes of the Group 14 Elements Group 14 Sandwich Complexes Half Sandwich Complexes of Group 14 Elements Tricyclopentadienyl Complexes Reaction Chemistry Metallocenes of the Pnictogens Factors Governing the Structure of Multicyclopentadienyl Complexes Conclusions Acknowledgments 46 References 47 2 Lanthanocenes F. T. Edelmann 2.1 Introduction Lanthanide(II) Metallocenes Lanthanide(III) Metallocenes Lanthanide(III) Metallocenes Containing Ln-Group 17 Element Bonds Lanthanide(III) Metallocenes Containing Ln-Group 16 Element Bonds Lanthanide(III) Metallocenes Containing Ln-Group 15 Element Bonds Lanthanide(III) Metallocenes Containing Ln-Group 14 Element Bonds Lanthanide(III) Metallocenes Containing Ln-Hydrogen Bonds Conclusion and Perspective Acknowledgments 104 References 104
4 VII 3 Group 3 Metallocenes P. J. Chirik and J. E. Bercaw 3.1 Introduction Synthesis of Group 3 Metallocenes Scandium Yttrium and Lanthanum Group 3 Metallocenes for the Activation of Hydrocarbons Group 3 Metallocenes as Homogeneous Olefin Polymerization Catalysts Reactions of Group 3 Metallocenes with Acetylenes Reactions of Group 3 Metallocenes with Group 6 Compounds Reactions of Group 3 Metallocenes with Other Small Molecules Applications of Group 3 Metallocenes in Organic Synthesis Photophysics of Group 3 Metallocenes Alternatives of Cyclopentadienyl Ligands Concluding Remarks 147 References Titanocenes R. Beckhaus 4.1 Introduction Bonding Modes of Cyclopentadienyl Ligands in Titanium Complexes Synthesis of Titanocene Complexes Sources of the Titanocene Fragment as a Versatile Building Block Electronic Properties of Titanocenes Titanocene Complexes in Low Oxidation States Substituents on the Cp Rings Ligands in the Coordination Sphere of Titanocenes Olefins Acetylenes Carbonyls Phosphines Hydrides Titanium Ligand Multiple Bonds Carbene Complexes Complexes Containing Ti-X Double Bonds (X: N, P, Chalcogenides) Metallocene Complexes of the Type [Cp 2 TiL 2 ]
![4.3.7.1 Aqua-Titanocene Complexe 173 4.3.7.2 Titanocene Complexes with Highly Fluorinated Ligand Systems... 174 4.3.7.3 Further Complexes with [Titanocene] 2 " 1 " (d ) and [Titanocene]" 1 " (d 1 ) Units 174 4.](/docs-images/83/88698347/images/5-0.jpg "4 Reactions in the Coordination Sphere of Titanocenes 175 4.4.1 The free Titanocenes 175 4.4.2 Reactions of Ti-C a Bonds 178 4.4.2.1 Reductive Elimination 179 4.4.2.2 Oxidative Addition 180 4.4.2.3 a-h Elimination 181 4.")
5 Aqua-Titanocene Complexe Titanocene Complexes with Highly Fluorinated Ligand Systems Further Complexes with [Titanocene] 2 " 1 " (d ) and [Titanocene]" 1 " (d 1 ) Units Reactions in the Coordination Sphere of Titanocenes The free Titanocenes Reactions of Ti-C a Bonds Reductive Elimination Oxidative Addition a-h Elimination ß-U Elimination Reactions of Ti=C Double Bonds Reactions with Electrophiles C-H Activation Reactions on [L n Ti=C] Fragments [2+1] Additions Cycloaddition Reactions with Acetylenes Synthesis and Reactivity of Metallaoxetanes Synthesis of Heterodinuclear Carbene Complexes with a Titanaoxetane Substructure Synthesis and Reactivity of Heterotitanacyclobutenes and-butanes Structure and Reactivity Pattern for small Titanacycles Dimetallic Compounds Derived from Ti=C Species Reactions Involving the Cp Ligand Analytical Data Structural Data NMR Data l H NMR Data C NMR Data Ti NMR Data UV vis Spectra Selected Applications of Titanocene Complexes C-C Coupling Reactions Dimerization of Ethylene Head to Tail Coupling Reactions of Acetylenes Cyclization Reactions Stoichiometric and Catalytic Reactions of Carbenoid Metal Complexes of Electron-Deficient Transition Metals Carbonyl Olefinations with Tebbe, Grubbs, and Petasis Reagents Ene Reactions Catalytic Reactions Cp-Equivalents Acknowledgments 230 References 230
6 IX 5 Zirconocenes E. Negishi andj.-l. Montchamp 5.1 Introduction Preparation of Cp 2 Zr Compounds Transmetallation Hydrozirconation Oxidative Addition Oxidative Coupling and Complexation Reactions and Synthetic Applications of Monoorganylzirconocene Derivatives Protonolysis, Halogenolysis, Oxidation, and Related Carbon-Heteroatom Bond Formation Reactions Protonolysis and Deuterolysis Halogenolysis Oxidation Carbon-Carbon Bond Formation via Polar Reactions of RZrCp 2 Cl with Carbon Electrophiles Reactions of Allylzirconocenes with Aldehydes Reactions of Cationic Alkyl- and Alkenylzirconocenes with Aldehydes, Epoxides, Ketones, and Nitriles Carbon-Carbon Bond Formation via Migratory Insertion Reactions of RZrCp 2 Cl Carbonylation Isonitrile Insertion Other Migratory Insertion Reactions Stoichiometric Carbozirconation of Monoorganylzirconocenes Reactions of Monoorganylzirconocenes via Transmetallation Stoichiometric Conversion of Monoorganylzirconocenes into Other Organometals Reactions of Monoorganylzirconocenes Catalyzed by Metal Complexes Organometallic Reactions Catalyzed by Zirconocene Derivatives Zirconium-Catalyzed Carboalumination and Carbozincation of Alkynes Zirconium-Catalyzed Hydroalumination and Hydroboration of Alkenes and Alkynes Zirconium-Catalyzed Enantioselective Carboalumination of Alkenes Reactions Involving n-complexes of Zirconocenes or Three- Membered Zirconacycles Formation of n-complexes of Zirconocenes 284
7 X Contents Stoichiometric Reactions of 71-Complexes of Zirconocenes (or Three-Membered Zirconacycles) Protonolysis and Halogenolysis Ring Expansion Reactions Regioisomerization, Stereoisomerization, cr-bond Metathesis, and Other Stoichiometric Reactions of Three-Membered Zirconacycles Stoichiometric Reactions of Five-Membered Zirconacycles Catalytic Reactions Involving Zirconacycles and Related Derivatives Zirconium-Catalyzed Carbomagnesiation Reactions Involving C-H Activation Zirconium-Catalyzed Carboalumination of Alkynes via C-H Activation Other Zirconium-Catalyzed Reactions Involving Cp 2 Zr(II) Complexes Conclusion 310 References Group 5 and Group 6 Metallocenes P. Royo and E. Ryan 6.1 Introduction Type A Metallocene Compounds Neutral Metallocenes Group 5 Metallocenes [MCp 2 ] Group 6 Metallocenes [MCp 2 ] Ionic Mettalocenes Group 5 Cationic Metallocenes [MCp 2 ] Group 5 Anionic Metallocenes [MCp 2 ]" Group 6 Cationic Metallocenes [MCp 2 ] Group 6 Anionic Metallocenes [MCp 2 ]' Type B-Bent bis(cyclopentadienyl) Metal Complexes with Mono-Functional Single-Atom Donor Monoanionic and Neutral Ligands Complexes with One Coordinated Ligand Neutral Group 6 [MCp 2 L] Metal Complexes Anionic Group 5 [MCp 2 L]" and Group 6 [MCp 2 X]" Metal Complexes Neutral Group 5 [MCp 2 L] and Group 6 [MCp 2 X] Metal Complexes 336
![XI 6.3.1.4 Anionic Group 5 [MCp2X]- and Cationic Group 6 [MCp 2 L] + Metal Complexes 339 6.3.1.5 Neutral d 2 Vanadium Compounds [VCp 2 X] 340 6.3.1.6 Neutral d 2 Niobium and Tantalum Compounds [(Nb,Ta)Cp 2 X] 344 6.](/docs-images/83/88698347/images/8-0.jpg "3.1.7 Cationic Group 5 d 2 Metal Compounds [MCp 2 L] + 345 6.3.1.8 Cationic Group 6 d 2 Metal Compounds [MCp 2 X] + 346 6.3.2 Complexes with Two Coordinated Ligands 346 6.3.2.1 Neutral Group 5 d 2 Metal Compounds [MCp 2 XL] 348 6.")
8 XI Anionic Group 5 [MCp2X]- and Cationic Group 6 [MCp 2 L] + Metal Complexes Neutral d 2 Vanadium Compounds [VCp 2 X] Neutral d 2 Niobium and Tantalum Compounds [(Nb,Ta)Cp 2 X] Cationic Group 5 d 2 Metal Compounds [MCp 2 L] Cationic Group 6 d 2 Metal Compounds [MCp 2 X] Complexes with Two Coordinated Ligands Neutral Group 5 d 2 Metal Compounds [MCp 2 XL] Cationic Group 5 d 2 Metal Compounds [MCp 2 L 2 ] Anionic Group 5 d 2 Metal Compounds [MCp 2 X 2 ]" Neutral Group 6 d 2 Metal Compounds [MCp 2 X 2 ] Cationic Group 6 d 2 Metal Compounds [MCp 2 XL] Dicationic Group 6 d 2 Metal Compounds [MCp 2 L 2 ] Neutral Group 5 d 1 Metal Compounds [MCp 2 X 2 ] Cationic Group 5 d 1 Metal Compounds [MCp 2 XL] +, [MCp 2 L 2 ] Cationic Group 6 d 1 Metal Compounds [MCp 2 X 2 ] Cationic Group 5 d Metal Compounds [MCp 2 X 2 ] +, [MCp 2 XL] Dicationic Group 6 d Metal Compounds [MCp 2 X 2 ] Complexes with Three Coordinated Ligands Neutral Group 5 d Metal Compounds [MCp 2 X 3 ] Cationic Group 5 d Metal Compounds [MCp 2 X 2 L] +, [MCp 2 XL 2 ] 2+ and [MCp 2 L 3 ] Cationic Group 6 d Metal Compounds [MCp 2 X 3 ] Type C - Complexes with Single-Atom Donor Dianionic Ligands Electron Compounds Neutral Group 5 d Metal Compounds [MCp 2 EX] Cationic Group 5 d Metal Compounds[MCp 2 EL] Neutral Group 6 d 2 Metal Compounds [MCp 2 E] Cationic Group 6 d Metal Compounds [MCp 2 EX] Electron Compounds Neutral d 1 Vanadium Compounds [VCp 2 E] Type D-Complexes with J7 2 -Side-Bonded Ligands Electron Compounds Neutral Group 5 d 2 Metal Compounds [MCp 2 (r7 2 -X-L)] Neutral Group 5 Metal Complexes [MCp 2 X(?7 2 -C-C)] or [MCp 2 X(?7 2 -C-Y)] (Y = N, O, or S) Anionic Group 5 d 2 Metal Compounds [MCp 2 (?7 2 -C,Y)] + and [MCp 2 X(77 2 -C,Y)] Neutral Group 6 d 2 Metal Compounds [MCp 2 (r7 2 -X-X)] Cationic Group 6 d 2 Metal Compounds [MCp 2 (?7 2 -X-L)] Neutral Group 5 d Metal Compounds [MCp 2 (?7 2 -X-X)Z] Cationic Group 5 d Metal Compounds [MCp^L]* and [MCp 2 (?7 2 -X-L)Z] + 401
![6.5.2 17-Electron Compounds 403 6.5.2.1 Neutral d 1 Vanadium Compounds [VCp 2 (r? 2 -X-X)] 403 6.5.2.2 Niobium Compounds [NbCp 2 (T7 2 -L-L)] and [NbCp 2 (T7 2 -C,Y)] 404 References 405 7 Half-Sandwich Complexes as Metallocene Analogs J.](/docs-images/83/88698347/images/9-0.jpg "Okuda and T. Eberle 7.1 Introduction 415 7.2 Complexes with Linked Amido-Cyclopentadienyl Ligands 417 7.2.1 Synthesis 417 7.2.2 Hydrido and Alkyl Complexes 424 7.2.3 Reactivity 429 7.2.4 Structure 431 7.")
9 Electron Compounds Neutral d 1 Vanadium Compounds [VCp 2 (r? 2 -X-X)] Niobium Compounds [NbCp 2 (T7 2 -L-L)] and [NbCp 2 (T7 2 -C,Y)] 404 References Half-Sandwich Complexes as Metallocene Analogs J. Okuda and T. Eberle 7.1 Introduction Complexes with Linked Amido-Cyclopentadienyl Ligands Synthesis Hydrido and Alkyl Complexes Reactivity Structure Complexes with Polydentate Amido-Cyclopentadienyl Ligands Complexes with two Amido-Cyclopentadienyl Ligands Complexes with Linked Alkoxo-Cyclopentadienyl Ligands Catalysis Polymerization of Ethylene, a-olefins and Dienes Hydrogenation and Hydroboration Conclusion 450 References Synthesis of Chirai Titanocene and Zirconocene Dichlorides R. L. Halterman 8.1 Introduction Ligand Chirality and Stereoisomeric Metal Complexes Unbridged Ligands Cyclopentadienes Indenes Bridged Ligands with Nonstereogenic Bridging Groups Bis(cyclopentadienes) Bis(indenes) Bis(fluorenes) Mixed Ligands Bridged Ligands with Stereogenic Bridging Groups Unbridged Metal Complexes Bis(cyclopentadienyl)metals 513
10 XIII Bis(indenes) Bis(fluorenes) Mixed Ligands Metal Complexes with Nonstereogenic Bridging Groups Bis(cyclopentadienyl)metals Bis(indenes) Bis(fluorenes) Mixed Ligands Metal Complexes with Stereogenic Bridging Groups 531 References 539
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