Fundamentals of Organometallic Catalysis

, by Steinborn, Dirk; Harmsen, Alexander

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ISBN: 9783527327164 | 3527327169
Cover: Hardcover
Copyright: 11/30/2011

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Clearly structured and written with advanced undergraduate, graduate and PhD students in mind, this English edition of a successful German textbook not only focuses on organic reactions, but also on bio-relevant reactions. Important aspects of the catalytic mechanisms are discussed in detail while much additional information is also provided, such as industrial applications of the processes covered. With its many questions and answers included in all chapters at different knowledge levels, this book is also ideal for self-testing before exams.

Preface	p. XIII
Index of Frequently Used Abbreviations	p. XV
Introduction	p. 1
The Beginnings of Catalytic Research	p. 1
Homogeneously Catalyzed Reactions	p. 1
Heterogeneously Catalyzed Reactions	p. 3
The Catalysis Definitions of Berzelius and Ostwald	p. 5
Berzelius' Catalysis Concept	p. 5
Ostwald's Definition of Catalysis	p. 6
Principles of Organometallic Catalysis	p. 9
Homogeneous versus Heterogeneous Catalysis	p. 9
Catalytic Cycles	p. 11
Activity and Productivity of Catalysts	p. 12
Catalytic Activity	p. 12
Catalytic Productivity	p. 12
Conversion Time Plots	p. 13
Selectivity and Specificity of Catalysts	p. 14
Determination of Catalytic Mechanisms	p. 15
Experimental Studies	p. 16
Theoretical Studies	p. 17
Glossary for Catalysis	p. 18
The Development of Organometallic Catalysis	p. 21
Elementary Steps in Organometallic Catalysis	p. 27
Cleavage and Coordination of Ligands	p. 27
Oxidative Addition and Reductive Elirnination	p. 30
Oxidative Coupling and Reductive Cleavage	p. 35
Olefin Insertion and p-Hydrogen Elimination	p. 37
¿-Hydrogen Elimination and Carbene Insertion Reactions	p. 40
Addition of Nucleophiles and Heterolytic Fragmentation	p. 42
Insertion and Extrusion of CO	p. 45
One Electron Reduction and Oxidation	p. 46
Hydrogenation of Olefins	p. 49
Introduction	p. 49
The Wilkinson Catalyst	p. 50
Principles	p. 50
Mechanism of Olefin Hydrogenation	p. 51
Enantioselective Hydrogenation	p. 54
Principles	p. 54
Applications and Examples	p. 58
Applications for Asymmetric Hydrogenation	p. 58
Combinatorial Catalysis	p. 59
Nonlinear Effects	p. 61
KineticaHy Controlled Enantioselectivity-A Closer Look	p. 63
Dihydrogen Complexes and H2 Activation	p. 68
Dihydrogen Complexes	p. 68
Activation of Dihydrogen	p. 71
Transfer Hydrogenation	p. 73
Hydroformylation of Olefins and Fischer-Tropsch Synthesis	p. 77
Cobalt Catalysts	p. 77
Phosphane Modified Rhodium Catalysts	p. 80
Enantioselecrive Hydroformylation	p. 84
Significance of Hydroformylation and Outlook	p. 88
Diphosphates as Ligands	p. 89
Biphasic Catalysis	p. 91
Synthesis of Vitamin A	p. 93
Carbon Dioxide as Alternative to CO	p. 93
Combinatorial and Supramolecular Catalysis	p. 94
The Fischer-Tropsch Synthesis	p. 95
Mechanism	p. 97
Carbonylation of Methanol and Water Gas Shift Reaction	p. 101
Principles	p. 101
The Monsanto Process	p. 103
Synthesis of Acetic Anhydride	p. 106
The Cativa Process	p. 108
Water Gas Shift Reaction and Carbon Monoxide Dehydrogenases	p. 112
Water Gas Shift Reaction	p. 112
Carbon Monoxide Dehydrogenases	p. 114
Metathesis	p. 117
Metathesis of Olefins	p. 117
Introduction	p. 117
Mechanism	p. 118
Catalysts	p. 119
Mechanism A Closer Look	p. 123
Metathesis of Cycloalkenes	p. 125
Metathesis of Acyclic Dienes	p. 128
Enantioselective Metathesis	p. 130
Metathesis of Alkynes	p. 131
Enyne Metathesis	p. 133
Bond Metathesis	p. 135
Metathesis of Alkanes	p. 137
Principles	p. 137
Mechanism	p. 138
Alkane Metathesis Via Tandem Reactions	p. 141
Oligomerization of Olefins	p. 145
Ziegler Growth Reaction	p. 145
Nickel Effect and Nickel-Catalyzed Dimerization of Ethene	p. 147
Trimerization of Ethene	p. 152
Shell Higher Olefin and ¿-Sablin Processes	p. 156
The Shell Higher Olefin Process (SHOP)	p. 156
¿-Sablin Process	p. 158
Use of Linear ¿-Olefins	p. 159
Polymerization of Olefins	p. 161
Introduction	p. 161
Ethene Polymerization	p. 162
Ziegler Catalysts	p. 162
Mechanism A Closer Look	p. 165
Phillips Catalysts	p. 167
Polymer Types and Process Specifications	p. 169
Propene Polymerization	p. 171
Regioselectivity and Stereoselectivity	p. 171
Ziegler-Natta Catalysts	p. 175
Polymer Types and Process Specifications	p. 178
Metallocene Catalysts	p. 179
Cocatalysts and Anion Influence	p. 179
C₂- and C_s- Symmetric Metallocene Catalysts	p. 182
Principles	p. 182
Mechanism	p. 184
Metallocene Catalysts with Diastereotopic Coordination Pockets	p. 187
Principles	p. 187
Hemitactic Polymers	p. 190
Stereoblock Polymers	p. 191
On the Significance of Metallocene Catalysts	p. 191
Nonmetallocene Catalysts	p. 193
Catalyst Systems of Early Transition Metals	p. 194
Catalyst Systems of Late Transition Metals	p. 194
Living Polymerization of Olefins and Block Copolymers	p. 198
Copolymerization of Olefins and CO	p. 200
Perfectly Alternating Copolymerization	p. 200
	p. 204
C C Linkage of Dienes	p. 207
Introduction	p. 207
Allyl and Butadiene Complexes	p. 208
Allyl Complexes	p. 208
Butadiene Complexes	p. 211
Re Si and supine prone Coordination of Allyl and Butadiene Ligands	p. 213
Organometallic Elementary Steps of Allyl Ligands	p. 214
Oxidative Coupling and Reductive Cleavage	p. 214
Butadiene Insertion and P-Hydrogen Elimination	p. 215
Allyl Insertion	p. 215
Oxidative Addition and Reductive Elimination	p. 226
anti/cis and syn/trans Correlations	p. 218
Oligomerization and Telomerization of Butadiene	p. 218
Cyclotrimerization of Butadiene	p. 228
Mechanism	p. 218
cis/trans Selectivity A Closer Look	p. 222
Industrial Synthesis of CDT	p. 224
Cyclodimerization of Butadiene	p. 224
Mechanism	p. 224
Selectivity Control	p. 226
Linear Oligomerization and Telomerization of Butadiene	p. 230
Polymerization of Butadiene	p. 234
Mechanism	p. 234
Butadiene Polymerization Catalyzed by Allylnickel (II) Complexes	p. 237
Synthesis and Properties of Polybutadienes and Polyisoprenes	p. 241
C-C Coupling Reactions	p. 245
Palladium Catalyzed Cross Coupling Reactions	p. 245
Introduction	p. 245
Mechanism of Cross Coupling Reactions	p. 246
Selected Types of Cross-Coupling	p. 249
Cross Coupling with Organolithium, Organomagnesium, and Organozinc Reagents	p. 249
Suzuki Coupling	p. 250
Hiyama Coupling	p. 252
Stille Coupling	p. 252
Sonogashira Coupling	p. 253
Ligand Effects	p. 254
Alkyl Alkyl Coupling	p. 255
Enantioselective Cross-Coupling	p. 256
Carbonylative Cross-Coupling	p. 258
The Heck Reaction	p. 258
Mechanism of Heck Reactions	p. 259
Mechanism A Closer Look	p. 260
Ligand Effects	p. 262
Enantioselective Heck Reactions	p. 263
Palladium-Catalyzed Allylic Alkylation	p. 264
Principles and Mechanism	p. 264
Chirality Transfer in Asymmetric Allylation	p. 267
Hydrocyanation, Hydrosilylation, and Hydroamination of Olefins	p. 272
Introduction	p. 271
Hydrocyanation	p. 272
Principles and Mechanism	p. 272
Mechanism A Closer Look	p. 273
The DuPont Adiponitrile Process	p. 274
Outlook	p. 276
Enantioselective Hydrocyanation	p. 276
Hydrocyanation of Alkynes	p. 277
Hydrocyanation of Polar C=X Bonds	p. 278
Hydrosilylation	p. 279
Principles and Mechanism	p. 279
Significance of Hydrosilylation and Outlook	p. 283
Applications	p. 283
Enantioselective Hydrosilylation	p. 284
Hydrosilylation of Alkynes	p. 285
Complexes of Silanes	p. 286
Hydroamination	p. 287
Principles	p. 287
Catalyst Types	p. 289
Alkali Metal Amides as Catalysts	p. 289
Platinum Group Metals as Catalysts	p. 289
Gold Complexes as Catalysts	p. 292
Lanthanoid Complexes as Catalysts	p. 292
Oxidation of Olefins and Alkanes	p. 295
The Wacker Process	p. 295
Introduction	p. 295
Mechanism of Ethene Oxidation	p. 297
Oxypalladation of Olefins	p. 303
Types of Oxypalladation	p. 303
Enantioselective Oxypalladation	p. 305
Palladium Oxidase Catalysis	p. 305
Epoxidation of Olefins	p. 306
Introduction	p. 306
Epoxidation of Ethene and Propene	p. 307
O2 and ROOH as Oxygen Transfer Agents	p. 307
Mechanism	p. 309
H2 O2as Oxygen Transfer Agent	p. 311
Enantioselecrive Oxidation of Olefins	p. 313
Epoxidation of Allyl Alcohols	p. 313
Epoxidation of Nonactivated Olefins	p. 314
Monooxygenases	p. 315
C-H Functionalization of Alkanes	p. 319
Introduction	p. 319
C-H Activation of Alkanes	p. 319
Cyclometallation and Orthometallation	p. 319
Intermolecular C-H Activation of Alkanes	p. 321
C-H Functionalization	p. 323
The Shilov Catalyst System	p. 324
The Catalytica System Hg" as Catalyst	p. 325
The Catalytica System Pt" as Catalystp326
Cytochrome P-450	p. 326
Nitrogen Fixation	p. 329
Fundamentals	p. 329
Heterogeneously Catalyzed Nitrogen Fixation	p. 334
Principles	p. 334
Mechanism of Catalysis	p. 335
The Industrial Catalyst	p. 338
Ruthenium Catalysts	p. 340
Enzyme Catalyzed Nitrogen Fixation	p. 342
The Fe Protein Cycle	p. 343
The MoFe Protein Cycle	p. 344
A Prebiotic Nitrogen Fixing System?	p. 347
Homogeneously Catalyzed Nitrogen Fixation	p. 348
Stoichiometric Reduction of N2 Complexes	p. 348
Catalytic Reduction of Dinirrogen	p. 352
Functionalization of Dinirrogen	p. 359
Solutions to Exercises	p. 363
Bibliography and Sources	p. 407
References	p. 408
Further Reading	p. 429
Source for Structures	p. 436
Index	p. 439
Index of Backgrounds	p. 456
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Fundamentals of Organometallic Catalysis

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