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	Volume 1: Applications


1	Introduction (B. Cornils, W.A. Herrmann)	1
	Introduction	3
	Historical Glossary	16
2	Applied Homogeneous Catalysis	29
2.1	Carbon Monoxide and Synthesis Gas Chemistry	31
2.1.1	Hydroformylation (Oxo Synthesis, Roelen Reaction) (C.D. Frohning, C.W. Kohlpaintner, H.-W. Bohnen)	31
2.1.1.1	Introduction	31
2.1.1.2	Fundamental Principles	34
2.1.1.3	Kinetics, Mechanism, and Process Parameters	45
2.1.1.4	Commercial Applications	61
2.1.1.5	Recent Developments	85
2.1.2	Carbonylations	104
2.1.2.1	Synthesis of Acetic Acid and Acetic Acid Anhydride from Methanol (P. Torrence)	104
2.1.2.2	Synthesis of Propionic and Other Acids (A. Höhn)	136
2.1.2.3	Carbonylation of Benzyl--X and Aryl--X Compounds (M. Beller)	145
2.1.2.4	Amidocarbonylation (J.F. Knifton)	156
2.1.2.5	Oxidative Carbonylation (A. Klausener, J.-D. Jentsch)	164
2.1.2.6	Other Carbonylations (M. Beller, A.M. Tafesh)	182
2.2	Hydrogenation (H. Brunner)	195
2.2.1	Homogeneous Hydrogenation	195
2.2.1.1	The Hydrogen Molecule	195
2.2.1.2	Classical Transition Metal Hydrides	195
2.2.1.3	Nonclassical Dihydrogen Complexes	196
2.2.1.4	Homogeneous Hydrogenation of Organic Substrates	198
2.2.1.5	Enantioselective Hydrogenation of Prochiral Substrates	200
2.2.1.6	Isolated Catalysts Versus in-situ Catalysts	203
2.2.1.7	Transfer Hydrogenation	204
2.2.1.8	Hydrogenolysis	204
2.2.1.9	Mechanisms	205
2.2.1.10	Industrial Applications	209
2.2.2	Commercial Enantioselective Hydrogenation	210
2.3	Reactions of Unsaturated Compounds	213
2.3.1	Polymerization, Oligomerization, and Copolymerization of Olefins	213
2.3.1.1	Chemical Background (W. Kaminsky, M. Arndt-Rosenau)	213
2.3.1.2	Chemical Engineering and Applications (L. L. Böhm)	230
2.3.1.3	Oligomerization of Ethylene to Higher Linear -Olefins (D. Vogt)	240
2.3.1.4	Dimerization and Codimerization (H. Olivier-Bourbigou, L. Saussine)	253
2.3.1.5	Evolution of the Synthesis of Group 4 Metallocene Catalyst Components Toward Industrial Production (C. Fritze, P. Müller, L. Resconi)	265
2.3.2	Reactions of Other Unsaturated Compounds	274
2.3.2.1	Reactions of Alkynes (J. Henkelmann, J.-D. Arndt, R. Kessinger)	274
2.3.2.2	Stereospecific Polymerization of Butadiene or Isoprene (R. Taube, G. Sylvester)	285
2.3.2.3	A Clean Route to Methacrylates via Carbonylation of Alkynes (E. Drent, W.W. Jager, J.J. Keijsper, F.G.M. Niele)	316
2.3.3	Metathesis (J.C. Mol)	328
2.3.3.1	Introduction	328
2.3.3.2	Scope of the Reaction	329
2.3.3.3	Reaction Mechanism and Catalysts in General	333
2.3.3.4	Homogeneous Catalyst Systems	335
2.3.3.5	Industrial Applications	339
2.3.3.6	Conclusions	341
2.3.4	The Alternating Copolymerization of Alkenes and Carbon Monoxide (E. Drent, J.A.M. van Broekhoven, P.H.M. Budzelaar)	344
2.3.4.1	Introduction	344
2.3.4.2	History of Polyketones	344
2.3.4.3	Copolymerization of Ethylene and CO	346
2.3.4.4	Scope of Olefin/CO Copolymerization	356
2.3.4.5	Conclusions	358
2.3.5	Telomerization (Hydrodimerization) of Olefins (N. Yoshimura)	361
2.3.5.1	Introduction	361
2.3.5.2	Development of Technologies	362
2.3.5.3	Process for the Manufacture of 1-Octanol	366
2.3.5.4	Development and Scope	366
2.3.6	Cyclooligomerizations and Cyclo-co-oligomerizations of 1,3-Dienes (G. Wilke, A. Eckerle)	368
2.3.6.1	Introduction	368
2.3.6.2	Cyclodimerization and Cyclotrimerization of Butadiene and Substituted 1,3-Dienes	370
2.3.6.3	Cyclo-co-oligomerization of 1,3-Dienes with Olefins and Alkynes	374
2.3.6.4	Mechanistic Considerations	377
2.3.6.5	Summary	379
2.3.7	Catalyzed Polymerisation of Epoxy Resins (M. Döring)	383
2.4	Oxidations	386
2.4.1	Oxidation of Olefins to Carbonyl Compounds (Wacker Process) (R. Jira)	386
2.4.1.1	Historical and Economic Background	386
2.4.1.2	Chemical Background	386
2.4.1.3	Kinetics and Mechanism	389
2.4.1.4	Technical Applications (Wacker--Hoechst-Processes)	397
2.4.1.5	Application of the Olefin Oxidation to Organic Syntheses	402
2.4.2	Homogeneous Oxidative Acetoxylation of Alkenes (I.I. Moiseev, M.N. Vargaftik)	406
2.4.2.1	Introduction	406
2.4.2.2	Mechanistic Considerations	407
2.4.2.3	Giant Cluster Catalyzed Reaction	409
2.4.3	Synthesis of Oxiranes (R.A. Sheldon)	412
2.4.3.1	Historical Development	412
2.4.3.2	Metal-Catalyzed Epoxidation with Alkyl Hydroperoxides: Kinetics and Mechanism	413
2.4.3.3	Commercial Oxirane Processes	417
2.4.3.4	Scope and Applications in Organic Synthesis	419
2.4.3.5	Recent Developments and Future Prospects	421
2.4.4	Aliphatic Carboxylic Acids via Aliphatic Aldehydes (F. Koch)	427
2.4.4.1	General	427
2.4.4.2	Catalysts	428
2.4.4.3	Kinetics and Mechanism	429
2.4.4.4	Technical Process	430
2.4.4.5	Future Trends	431
2.4.5	Oxidation of Arenes and Alkyl-Substituted Aromatic Compounds	433
2.4.5.1	Oxidation of Arenes to Quinones (R.W. Fischer)	433
2.4.5.2	Oxidation of Alkyl-Substituted Aromatic Compounds with Air (R.W. Fischer, F. Röhrscheid)	443
2.5	Reactions with Hydrogen Cyanide (Hydrocyanation) (S. Krill)	468
2.5.1	Introduction and Scope	468
2.5.2	Mechanistic Aspects of Hydrocyanation	469
2.5.3	Hydrocyanation of Olefins	470
2.5.3.1	Hydrocyanation of Non-Activated Monoolefins	470
2.5.3.2	Hydrocyanation of Functionalized Olefins	476
2.5.4	Hydrocyanation of Alkynes	479
2.5.5	Hydrocyanation of Dienes	481
2.5.5.1	Adiponitrile Synthesis via Hydrocyanation of Butadiene	481
2.5.5.2	Hydrocyanation of Other Dienes	484
2.5.6	Hydrocyanation of Aldehydes/Ketones	485
2.6	Hydrosilylation and Related Reactions of Silicon Compounds (B. Marciniec)	491
2.6.1	Hydrosilylation	491
2.6.1.1	General Scope and Applications	491
2.6.1.2	Homogeneous Catalysts	495
2.6.1.3	Immobilized Metal Complexes as Catalysts	500
2.6.1.4	Photo- and Peroxide-Initiated Catalysis by Metal Complexes	501
2.6.2	Dehydrogenative Coupling Reactions	502
2.6.2.1	Dehydrogenative Silylation of Alkenes and Alkynes with Hydrosilanes	502
2.6.2.2	Silylative Coupling of Alkenes with Vinylsilanes	504
2.6.2.3	Dehydrocoupling of Hydrosilanes	505
2.6.3	Silylcarbonylation	506
2.7	Reaction with Nitrogen Compounds: Hydroamination (R. Taube)	513
2.7.1	Introduction	513
2.7.2	General Mechanistic Aspects	513
2.7.3	The Different Catalyst Systems	516
2.7.3.1	Catalyst Systems Containing Alkali Metals	516
2.7.3.2	Catalyst Systems Containing Lanthanides	518
2.7.3.3	Catalyst Systems Containing Iridium	520
2.7.3.4	Catalyst Systems Containing Iron or Ruthenium	522
2.7.3.5	Catalyst Systems Containing Rhodium	522
2.7.4	Perspectives	524
2.8	Reactions of Hydrocarbons and Other Saturated Compounds	525
2.8.1	Oxidations	525
2.8.1.1	Homogeneous Catalysis in the Oxidation of Hydrocarbons to Acetic Acid (C.C. Hobbs, Jr.)	525
2.8.1.2	Synthesis of Dimethyl Terephthalate/Terephthalic Acid and Poly(ethylene terephthalate) (D.A. Schiraldi)	544
2.8.2	Halogenations (W.A. Herrmann, M. Stoeckl)	552
2.8.2.1	Introduction	552
2.8.2.2	Substitution Reactions	552
2.8.2.3	Addition Reactions	553
2.9	Asymmetric Syntheses (R. Noyori, S. Hashiguchi, T. Yamano)	557
2.9.1	Introduction	557
2.9.2	Preparation of Selected Structures	557
2.9.2.1	Terpenes	557
2.9.2.2	Carboxylic Acids	559
2.9.2.3	Pyrethroids	563
2.9.2.4	Prostaglandins	565
2.9.2.5	Simple Secondary Alcohols	565
2.9.2.6	Amino Alcohols and Related Compounds	568
2.9.2.7	Amino Acids	572
2.9.2.8	Alkaloids	574
2.9.2.9	Carbapenem Antibiotics	576
2.9.2.10	Sulfoxides	577
2.9.2.11	1,2-Diols and Related Compounds	578
2.9.2.12	Miscellaneous	578
2.9.3	Conclusions	580
2.10	Ferrocene as a Gasoline and Fuel Additive (W.A. Herrmann)	586
2.10.1	Introduction	586
2.10.2	Commercial Synthesis	586
2.10.3	The Gasoline and Fuel Additive	588
2.10.4	Related Antiknocking Additives	589
2.11	The Suzuki Cross-Coupling (W.A. Herrmann)	591
2.11.1	Introduction	591
2.11.2	Advantages and Drawbacks	591
2.11.3	Catalysts, Substrates, Conditions	592
2.11.3.1	Current Status	592
2.11.3.2	Recent Catalyst Improvements	592
2.11.3.3	Two-Phase Catalysis	595
2.11.3.4	Suzuki-Related Coupling	595
2.11.4	Mechanism	596
2.11.5	Commercial Application and Further Development	597


	Volume 2: Developments


3	Recent Developments in Homogeneous Catalysis	599
3.1	Development of Methods	601
3.1.1	Homogeneous Catalysts and Their Heterogenization or Immobilization (B. Cornils, W.A. Herrmann)	601
3.1.1.1	Immobilization by Aqueous Catalysts (B. Cornils, W.A. Herrmann)	603
3.1.1.2	Immobilization by Other Liquids	634
3.1.1.2.1	Fluorous Phases (I. T. Horváth)	634
3.1.1.2.2	Non-Aqueous Ionic Liquids (V.P.W. Böhm)	639
3.1.1.3	Immobilization (P. Panster, S. Wieland)	646
3.1.1.4	Surface Organometallic Chemistry (J.-M. Basset, G.P. Niccolai)	664
3.1.1.5	Ligand-Stabilized Clusters and Colloids (G. Schmid)	677
3.1.1.6	New Generation of Re-Immobilized Catalysts (H. Bahrmann)	684
3.1.1.7	New Reactions (J. Herwig)	694
3.1.2	Molecular Modeling in Homogeneous Catalysis (R. Schmid, W. Hieringer, D. Gleich, T. Strassner)	700
3.1.2.1	Molecular Modeling Techniques (R. Schmid)	700
3.1.2.2	Applications	712
3.1.2.2.1	Modeling of Homogeneous Olefin Polymerization Catalysts (R. Schmid)	712
3.1.2.2.2	Palladium-Catalyzed C--C Couplin Reactions: The Heck Reaction (W. Hieringer)	721
3.1.2.2.3	Hydroformylation (D. Gleich)	727
3.1.2.2.4	C--H Activation (T. Strassner)	737
3.1.3	High-Throughput Approaches to Homogeneous Catalysis (V. Murphy, H.W. Turner, T. Weskamp)	740
3.1.3.1	Introduction	740
3.1.3.2	Principal Workflow	741
3.1.3.3	Analysis in High-Throughput Format	745
3.1.3.4	Data Management and Software	746
3.1.3.5	Discovery Screening Workflow for New Polyolefin Catalysts	747
3.1.4	Chemical Reaction Engineering Aspects of Homogeneously Catalyzed Processes (M. Baerns, P. Claus)	748
3.1.4.1	Kinetics in Homogeneous Catalysis	750
3.1.4.2	Aspects of Catalyst Recycling	759
3.1.5	Introduction to Selected Multicomponent and Multifunctional Catalysts (D. Hesse)	762
3.1.5.1	Introduction	762
3.1.5.2	Advantages in the Use of Multicomponent or Multifunctional Catalysts	764
3.1.5.3	Problems in the Use of Multifunctional or Multicomponent Catalysts	772
3.1.5.4	Conclusions	773
3.1.6	Catalytic Carbon--Carbon Coupling by Palladium Complexes: Heck Reactions (W.A. Herrmann)	775
3.1.6.1	Introduction	775
3.1.6.2	History	775
3.1.6.3	Definition	776
3.1.6.4	Catalysts and Reaction Conditions	777
3.1.6.5	Scope and Limitations	778
3.1.6.6	Mechanism	782
3.1.6.7	Catalyst Deactivation	784
3.1.6.8	Industrial Applications and Perspectives	786
3.1.7	Catalytic Cyclopropanation (A.F. Noels, A. Demonceau)	793
3.1.7.1	Introduction	793
3.1.7.2	Transition Metal Catalyzed Cyclopropanations	794
3.1.7.3	Recent Developments and Applications	798
3.1.7.4	Conclusion: In Search of New Catalysts	805
3.1.8	The Fischer--Tropsch Synthesis - Molecular Models for Homogeneous Catalysis? (W.A. Herrmann)	808
3.1.8.1	Introduction	808
3.1.8.2	Historical and Economic Background	809
3.1.8.3	Technological Features	811
3.1.8.4	Mechanistic Considerations	811
3.1.8.5	Assessment and Perspectives	819
3.1.9	Arene Coupling Reactions (W.A. Herrmann)	822
3.1.9.1	Introduction	822
3.1.9.2	Aryl--Aryl Coupling	823
3.1.9.3	Grignard Cross-Coupling	824
3.1.9.4	Phenol Coupling	826
3.1.9.5	Perspectives	827
3.1.10	Tailoring of Catalysts: N-Heterocyclic Carbenes as an Example of Catalyst Design (W.A. Herrmann, K. Denk, C.W.K. Gstöttmayr)	829
3.1.10.1	Introduction	829
3.1.10.2	Ligand Design for N-Heterocyclic Carbenes (NHC)	829
3.1.10.3	Catalytic Applications	832
3.1.11	Micellar Catalysis (G. Oehme)	835
3.1.11.1	Introduction	835
3.1.11.2	Examples of Micellar-Promoted Reactions	837
3.1.11.3	Reactions in Reverse Micelles	839
3.11.1.4	Limits and New Developments	840
3.1.12	Sulfur in Homogeneous Catalysis (P. Kalck, P. Serp)	842
3.1.12.1	Introduction	842
3.1.12.2	Sulfur in Carbonylation Reactions	843
3.1.12.3	Sulfur in Hydrogenation, Isomerization, and Related Reactions	845
3.1.12.4	Sulfur in CarbonCarbon Coupling Reactions	846
3.1.12.5	Miscellaneous Reactions	847
3.1.12.6	Conclusions	848
3.1.13	Homogeneous Catalysis Using Supercritical Fluids (W. Leitner)	852
3.1.13.1	Introduction	852
3.1.13.2	Single-Phase Catalysis Using SCFs as Solvents	854
3.1.13.3	Multiphase Catalysis Using SCFs as Solvents	862
3.1.13.4	Conclusions and Outlook	867
3.2	Special Catalysts and Processes	872
3.2.1	Biocatalysis and Enzyme-Analogous Processes (C. Schultz, H. Gröger, C. Dinkel, K. Drauz, H. Waldmann)	872
3.2.1.1	Introduction	872
3.2.1.2	Examples of Enzymatic Conversions	873
3.2.1.3	Enzyme-Analogous Catalysts	886
3.2.1.4	Commercial Applications	887
3.2.1.5	Outlook	906
3.2.2	Template or Host/Guest Relations (F. Vögtle, R. Hoss, M. Händel)	911
3.2.2.1	Introduction	912
3.2.2.2	Metal Cations as Templates	913
3.2.2.3	Neutral Molecules as (Supramolecular) Templates	914
3.2.2.4	Covalent Molecules as Templates	922
3.2.2.5	Kinetic and Thermodynamic Template Effects	926
3.2.2.6	Positive and Negative Templates	928
3.2.2.7	Self-Organization	928
3.2.2.8	Further Developments and Applications	935
3.2.2.9	Conclusions and Outlook	937
3.2.3	Membrane Reactors in Homogeneous Catalysis (U. Kragl, C. Dreisbach)	941
3.2.3.1	Introduction	941
3.2.3.2	Classification and Examples of Membrane Reactors	942
3.2.3.3	Membrane Reactors for Homogeneously SolubleCatalysts	947
3.2.3.4	Summary and Outlook	950
3.2.4	Phase-Transfer Catalysis and Related Systems (Y. Goldberg, H. Alper)	953
3.2.4.1	Introduction	953
3.2.4.2	Homogeneous Transition-Metal Catalyzed Reactions Under Phase-Transfer Conditions	954
3.2.4.3	Transition-Metal Containing Phase-Transfer Agents and Their Use in Synthesis	968
3.2.4.4	Conclusions	969
3.2.5	Rare Earth Metals in Homogeneous Catalysis (R. Anwander)	974
3.2.5.1	Introduction	974
3.2.5.2	Catalytic Potential	976
3.2.5.3	Precatalysts	977
3.2.5.4	Carbon--Carbon Bond-Forming Reactions	978
3.2.5.5	Carbon--Heteroelement Bond-Forming Reactions	997
3.2.5.6	Catalyst Structure	1005
3.2.5.7	Perspectives	1007
3.2.6	Recent Progress in Special Phosphorus-Containing Auxiliaries for Homogeneous Enantioselective Catalysis (F. Agbossou-Niedercorn)	1014
3.2.6.1	Introduction	1014
3.2.6.2	Monophosphines	1015
3.2.6.3	Bi(di,bis)phosphines	1020
3.2.6.4	Heterofunctionalized Multidentate P-Containing Chiral Auxiliaries	1024
3.2.6.5	Immobilization and Recycling	1025
3.2.6.6	Conclusions	1027


	Volume 3: Developments (continued)


3.2.7	Homologation (H. Bahrmann)	1034
3.2.7.1	Historical Background	1034
3.2.7.2	Chemical Basics and Applications	1035
3.2.7.3	Mechanism of Reaction	1040
3.2.7.4	Technical Applications	1042
3.2.7.5	Future Prospects	1044
3.2.8	Homogeneous Electrocatalysis (D. Astruc)	1046
3.2.8.1	Introduction	1046
3.2.8.2	Electron-Transfer-Chain (ETC) Catalyzed Reactions	1047
3.2.8.3	Atom-Transfer-Chain (ATC) Catalysis	1055
3.2.8.4	Conclusions	1057
3.2.9	Homogeneous Photocatalysis (A. Heumann, M. Chanon)	1060
3.2.9.1	Definitions	1060
3.2.9.2	Synthesis and Activation -- What hv Metal Catalysis Can Do Better?	1065
3.2.9.3	Conclusion: What Photochemical Techniques Can Provide in Mechanistic Studies of Transition Metal Catalysis	1074
3.2.10	Olefins from Aldehydes (W.A. Herrmann)	1078
3.2.10.1	Introduction	1078
3.2.10.2	The Catalytic Approach	1079
3.2.10.3	Catalysts	1080
3.2.10.4	Scope of Reaction, Reagents, and Side Reactions	1081
3.2.10.5	Mechanism	1082
3.2.10.6	Perspectives	1085
3.2.11	Water-Gas Shift Reaction (W.A. Herrmann, M. Muehlhofer)	1086
3.2.11.1	Introduction	1086
3.2.11.2	Definition	1087
3.2.11.3	Mechanism	1087
3.2.11.4	Applications	1089
3.2.11.5	The Arco Ethylurethane Process	1090
3.2.11.6	Catalytic Implications and Perspectives	1091
3.2.12	Catalytic McMurry Coupling: Olefins from Keto Compounds (W.A. Herrmann, H. Schneider)	1093
3.2.12.1	Introduction	1093
3.2.12.2	Stoichiometric Titanium Compounds, Other Reagents, and Mechanistic Aspects	1094
3.2.12.3	Catalytic Deoxygenation	1096
3.2.12.4	Perspectives	1097
3.2.13	Catalytic Hydrogenation of Heterocyclic Sulfur and Nitrogen Compounds in Raw Oils (C. Bianchini, A. Meli, F. Vizza)	1099
3.2.13.1	Introduction	1099
3.2.13.2	Hydrogenation of Sulfur Heterocycles	1100
3.2.13.3	Hydrogenolysis of Sulfur Heterocycles	1106
3.2.13.4	Hydrodesulfurization in Different Phase Variation Systems	1109
3.2.13.5	Hydrogenation of Nitrogen Heterocycles	1109
3.2.13.6	Hydrogenolysis of Nitrogen Heterocycles	1116
3.2.13.7	Perspectives	1116
3.2.14	Double-Bond Isomerization of Olefins (W.A. Herrmann, M. Prinz)	1119
3.2.14.1	Introduction	1119
3.2.14.2	Catalysts, Scope, and Definition	1120
3.2.14.3	Mechanistic Considerations	1121
3.2.14.4	Applications	1124
3.2.14.5	Asymmetric Isomerization	1125
3.2.14.6	Recent Developments	1126
3.2.14.7	Perspectives	1128
3.3	Special Products	1131
3.3.1	Enantioselective Synthesis (H.-U. Blaser, B. Pugin, F. Spindler)	1131
3.3.1.1	Introduction and Background	1131
3.3.1.2	Critical Factors for the Technical Application of Homogeneous Enantioselective Catalysts	1132
3.3.1.3	State-of-the-Art and Evaluation of Catalytic Transformations	1134
3.3.1.4	Conclusions and Prospects	1146
3.3.2	Diols via Catalytic Dihydroxylation (M. Beller, K.B. Sharpless)	1149
3.3.2.1	Introduction	1149
3.3.2.2	History and General Features of Osmium-Catalyzed Dihydroxylation Reactions	1150
3.3.2.3	Mechanism of Osmium-Catalyzed Dihydroxylations	1152
3.3.2.4	Scope and Limitation of Asymmetric Dihydroxylation	1153
3.3.2.5	Selected Applications of Osmium-Catalyzed Dihydroxylations	1159
3.3.3	Hydrovinylation (P.W. Jolly, G. Wilke)	1164
3.3.3.1	Introduction	1164
3.3.3.2	The Catalyst	1165
3.3.3.3	The Product	1169
3.3.3.4	The Mechanism	1178
3.3.3.5	Outlook	1184
3.3.3.6	Postscript	1185
3.3.4	Carbon Dioxide as a C1 Building Block (E. Dinjus, R. Fornika, S. Pitter, T. Zevaco)	1189
3.3.4.1	Introduction	1189
3.3.4.2	Catalytic CC Bond-Forming Reactions	1191
3.3.4.3	Transition Metal Catalyzed Formation of Formic Acid and its Derivatives from CO₂and H₂	1196
3.3.4.4	Catalyzed Formation of Organic Carbonates	1205
3.3.4.5	Summary and Outlook	1208
3.3.5	Reductive Carbonylation of Nitro Compounds (M. Dugal, D. Koch, G. Naberfeld, C. Six)	1214
3.3.5.1	Introductory Remarks	1214
3.3.5.2	Synthesis of Isocyanates	1214
3.3.5.3	Thermodynamics, Kinetics, and Mechanism	1218
3.3.5.4	Outlook	1223
3.3.6	New Approaches in CH Activation of Alkanes (A. Sen)	1226
3.3.6.1	Introduction	1226
3.3.6.2	Radical Pathways	1227
3.3.6.3	Oxidative Addition Pathways	1229
3.3.6.4	Electrophilic Pathways	1231
3.3.6.5	Conclusions	1238
3.3.7	PausonKhand Reaction (W.A. Herrmann)	1241
3.3.7.1	Introduction	1241
3.3.7.2	The Catalytic Option	1242
3.3.7.3	Related Reactions	1244
3.3.7.4	Stereoselective PKRs and Hetero-Reactions	1245
3.3.7.5	Degenerate (Intermittent) and Domino PK Reactions	1246
3.3.7.6	Substitution Effects, Selectivity, and Mechanism	1247
3.3.7.7	Commercial Perspectives	1249
3.3.7.8	Outlook	1250
3.3.8	Cyclooligomerization of Alkynes (H. Bönnemann, W. Brijoux)	1252
3.3.8.1	Introduction	1252
3.3.8.2	Survey of the Catalysts	1253
3.3.8.3	Five- and Six-Membered Heterocycles	1254
3.3.8.4	Six- and Eight-Membered Carbocycles	1261
3.3.9	Chemicals from Renewable Resources (J.P. Zoller)	1268
3.3.9.1	Introduction and General Developments	1268
3.3.9.2	"Oleo Chemistry"	1268
3.3.9.3	The Chemistry of Carbohydrates	1271
3.3.9.4	The Chemistry of Starch	1271
3.3.10	Special Reactions in Homogeneous Aqueous Systems	1274
3.3.10.1	Synthesis of Polymers (B.M. Novak)	1274
3.3.10.2	Homogeneous Catalysis in Living Cells (L. Vígh, F. Jo)	1283
3.3.11	Cyclic Hydrocarbons from Diazoalkanes (W.A. Herrmann, Horst Schneider)	1290
3.3.11.1	Introduction	1290
3.3.11.2	Scope and Definition	1290
3.3.11.3	Mechanistic Considerations	1291
3.3.11.4	Catalytic Cyclization	1292
3.3.11.5	Enantioselective Cyclization	1295
3.3.11.6	Perspectives	1295
3.3.12	Acrolein and Acrylonitrile from Propene (W.A. Herrmann)	1297
3.3.12.1	Introduction	1297
3.3.12.2	Scope and Technological Features	1297
3.3.12.3	Catalyst Principles and Mechanism	1298
3.3.12.4	Organometallic Models	1300
3.3.12.5	The "Amm(on)dehydrogenation"	1301
3.3.12.6	Perspectives	1303
3.3.13	Chemistry of Methyltrioxorhenium (MTO)	1304
3.3.13.1	Fine Chemicals via Methyltrioxorhenium as Catalyst (F.E. Kühn, M. Groarke)	1304
3.3.13.2	Pilot-Plant Synthesis of MTO (W.A. Herrmann)	1319
3.3.14	Acetoxylations and Other Palladium-Promoted or Palladium-Catalyzed Reactions (R. Jira)	1323
3.3.14.1	Historical and Economic Background	1323
3.3.14.2	Chemical Background	1323
3.3.14.3	Kinetics and Mechanism	1325
3.3.14.4	Commercial Processes	1329
3.3.14.5	Transvinylation	1331
3.3.14.6	Acetoxylation in Organic Synthesis	1332
3.3.14.7	Other Palladium-Promoted or Palladium-Catalyzed Reactions	1333
3.3.14.8	Conclusions	1336
4	Epilogue	1341
4.1	Homogeneous Catalysis -- Quo vadis? (W. A. Herrmann, B. Cornils)	1343
4.1.1	Immobilization of Homogeneous Catalysts	1345
4.1.2	Colloidal Organometallic Catalysts	1347
4.1.3	Multicomponent and Multifunctional Catalysis	1347
4.1.4	Stereoselective Catalysis	1348
4.1.5	Metals from Stoichiometric Reactivity to Catalytic Efficiency	1351
4.1.6	Mechanistic Knowledge and Theory -- Keys to Catalyst Design	1352
4.1.7	Catalyst Performance/New Techniques to Generate and Activate Catalysts	1353
4.1.8	Organometallic Electrocatalysis and Biomimetic Catalysis	1354
4.1.9	New Chemical Feedstocks for Homogeneous Catalysis and Renewable Resources	1356
4.1.10	Catalysis under Supercritical Conditions and Supported by Ionic Liquids	1362
4.1.11	New Reactions, Improved Catalysts	1365
4.1.12	A New Generation of Catalyst Ligands	1368
4.1.13	Rare Earth Catalysts	1369
4.1.14	Organometallic Catalysts for Polymers	1371
4.1.15	Catalyst Reactivation, Process, and Reactor Technology	1375
4.1.16	Final Closure	1375
	Index	1383

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