ISBN 978-3-527-32897-0
www.wiley-vch.de
The completely revised third edition of this four-volume classic is fully updated and now includes such topics as self-organization and organocatalysis. It describes the most important reaction types, new methods and recent developments.
The internationally renowned editors and a plethora of international authors (in-cluding Nobel laureate R. Noyori) guarantee high quality content throughout the book.
A „must read“ for everyone in academia and industry working in this field.
1
Cornils•H
errmann
Beller•Paciello(Eds.)
Volume 1 of 4
Applied
Hom
ogeneousCatalysis
with
Organom
etallicCom
pounds 3rd
Edition
Boy Cornils has worked at the Ruhrchemie AG in Oberhausen, Germany, where homogeneous catalysis started with the hydroformylation reaction found by Otto Roelen, and with the former Hoechst AG in Frankfurt, Germany. In both locations he was director of the research. He is editor of several bestselling titles.
Wolfgang A. Herrmann is president of the Technical University of Munich and has received several awards for his work in organometallic chemistry, like the Otto-Bayer Medal, the DFG Leibniz Award, the ACS Award in Organometallic Chemistry, Max Planck Research Award, the GDCh Wilhelm Klemm Award and many more. He has authored a plethora of publications and is the editor of numerous bestselling books.
Matthias Beller is director of the Leibniz-Institute for Catalysis and Professor for Catalysis at the University of Rostock. He has received several awards such as the Otto-Roelen Medal, the DFG Leibniz Award, the first European Prize for Sustainable Chemistry, the Emil Fischer Medal and the Wöhler Prize of the German Chemical Society and the Gay-Lussac-Alexander-von-Humboldt Prize.
Rocco Paciello is a research manager at BASF SE in Ludwigshafen, Germany. After experience as a research chemist and assistant plant manager, he became responsible for the homogeneous catalysis group at BASF and has led it for the last fifteen years. The group is focused on finding new technical applications of transition metal catalyzed homogeneous catalysis, such as hydroformylations, carbonylations and hydrogenations.
Edited by B. Cornils, W. A. Herrmann, M. Beller, R. Paciello
Applied Homogeneous Catalysis with Organometallic Compounds A Comprehensive Handbook in Four Volumes
Third Edition
Edited by Boy Cornils,Wolfgang A. Herrmann,Matthias Beller, andRocco Paciello
Applied HomogeneousCatalysis withOrganometallicCompounds
Edited by Boy Cornils, Wolfgang A. Herrmann,Matthias Beller, and Rocco Paciello
Applied Homogeneous Catalysis withOrganometallic Compounds
A Comprehensive Handbook in Four Volumes
Third Edition
Editors
Prof. Dr. Boy CornilsKirschgartenstr. 665719 HofheimGermany
Prof. Dr. Wolfgang A. HerrmannTechnische Universität MünchenAnorganische ChemieLichtenbergstr. 485747 GarchingGermany
Prof. Dr. Matthias BellerUniversität RostockLeibniz Institut für KatalyseAlbert-Einstein-Str. 29 a18059 RostockGermany
Dr. Rocco PacielloBasic Chemicals ResearchBASF AktiengesellschaftGCB/H-M 31367200 LudwigshafenGermany
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V
Contents
List of Contributors XVPreface to the Third Edition XXIX
Volume 1
1 Introduction 1Wolfgang A. Herrmann and Boy Cornils
1.1 Historical Pathways 11.2 Topical Developments Since Year 2000 91.3 Organization of the Third Edition 111.4 Historical Glossary 13
References 18
Part A Applied Homogeneous Catalysis 23
2 Hydroformylation 252.1 General Aspects 25
Boy Cornils2.2 Conventional Processes 262.3 Aqueous-Phase Process 71
Ernst Wiebus, Klaus Schmid, and Boy CornilsReferences 78
3 Carbonylation 913.1 Carbonylation: Introduction and General Aspects 91
Matthias Beller3.2 Carbonylation of Methanol and its Derivatives to Acetic
Acid and Acetic Anhydride 93Bradley A. Steinhoff and Joseph R. Zoeller
3.3 Alkyne Carbonylation 118David J. Cole-Hamilton, and Eite Drent
3.4 Aryl-X and Related Carbonylations 145Matthias Beller
ContentsVI
3.5 Transition Metal-Catalyzed Oxidative Carbonylations 149Xiao-Feng Wu, Helfried Neumann, and Matthias Beller
3.6 Alternating Copolymerization with Carbon Monoxide 156Shingo Ito and Kyoko NozakiReferences 178
4 Polymerization and Copolymerization 1914.1 General Aspects 191
Klaus Beckerle and Jun Okuda4.2 Metallocene-Catalyzed Polyolefins 203
Walter Kaminsky and Gerrit A. Luinstra4.3 Post- and Non-metallocenes for Olefin Insertion Polymerization 225
Moritz C. Baier and Stefan Mecking4.4 Polymerization of 1,3-Butadiene with Organometallic Complexes-Based
Catalysts 248Giovanni Ricci and Giuseppe Leone
4.5 Polycarbonates 273Leslaw Mleczko, Aurel Wolf, and Alexandra Grosse BöwingReferences 285
5 Oligomerization, Cyclooligomerization, Dimerization 3075.1 Selective Production of 1-Hexene and 1-Octene 307
Uwe Rosenthal, Bernd H. Müller, Normen Peulecke, Stephan Peitz,Anina Wöhl, and Wolfgang Müller
5.2 Dimerization and Selective Oligomerization – Selected Examples ofIndustrial Applications 328Hélène Olivier-Bourbigou and Lionel Magna
5.3 Telomerization of 1,3-Butadiene 343Piet W.N.M. van Leeuwen and Mathieu J.-L. Tschan
5.4 Cyclotrimerization Reactions of Alkynes 375Marko Hapke, Nico Weding, and Karolin KralAbbreviations 392References 392
Volume 2
6 Cross Coupling Reactions 4116.1 Coupling Reactions: Introduction and General Aspects 411
Matthias Beller6.2 Industrial Applications of Palladium-Catalyzed Coupling
Reactions 413Alejandro Varela-Fernandez and Johannes G. de Vries
6.3 Ligand-Enabled Palladium-Catalyzed C-N and C-O Bond Formationsfrom Aryl Halides, Tosylates and Mesylates 435Shung Man Wong, Chau Ming So, and Fuk Yee KwongReferences 459
VIIContents
7 Oxidation 4657.1 General Aspects 465
Joaquim Henrique Teles7.2 Aromatic Carboxylic Acids 469
Walt Partenheimer7.3 Oxidation of Olefins to Carbonyl Compounds (Wacker Process) 488
Reinhard Jira7.4 Radical Chain Oxidations 508
Fabrizio Cavani and Giorgio Strukul7.5 Manganese and Iron Bleaching Catalysts 519
Ronald Hage and Johannes W. de Boer7.6 Catalytic Decarbonylative and Decarboxylative Processes 524
Lukas Gooßen and Patrizia Mamone7.7 Oxidation of Phenols 543
Oxana A. KholdeevaReferences 550
8 Hydrosilylation and Related Reactions of Silicon Compounds 569Bogdan Marciniec, Hieronim Maciejewski, Cezary Pietraszuk, and Piotr Pawluc
8.1 Introduction 5698.2 Hydrosilylation of Carbon–Carbon Multiple Bonds 5718.3 Chemo- and Enantioselective Hydrosilylation of Unsaturated
Carbon–Heteroatom Bonds 5928.4 Silicometallics and Catalysis 598
References 605
9 Hydrogenation 6219.1 Industrial Application of Asymmetric Hydrogenation 621
Hans Ulrich Blaser, Benoît Pugin, and Felix Spindler9.2 Hydrogenation of Esters 645
Lionel A. SaudanAbbreviations 681References 682
Part B Recent Developments 691
Subpart 1: Catalysts 691
10 New Trends in Organometallic Catalysts 69310.1 Iron Catalysis 693
Kathrin Junge, Gerrit Wienhöfer, and Matthias Beller10.2 Copper-Catalyzed Arylation of Nucleophiles: History, Renaissance and
Scalable Reactions 744Anis Tlili, Gwilherm Evano, and Marc Taillefer
10.3 Rare Earth Metal Catalysts 764Rhett Kempe
VIII Contents
10.4 Chiral Frustrated Lewis Pair Catalysts 773Christoph Malbertz and Jürgen KlankermayerReferences 787
Volume 3
11 New Ligands 80911.1 N-Heterocyclic Carbenes 809
Rubén S. Ramón and Steven P. Nolan11.2 Phosphorus Ligands in Homogeneous Catalysis 828
Armin Börner and Ralf Jackstell11.3 Host–Guest Relations and Self-Organization in Homogeneous
Catalysis 846Frédéric Hapiot and Eric Monflier
11.4 Micellar Catalysis 863Michael Schwarze and Reinhard Schomäcker
11.5 Switchable Catalysis 877David E. Bergbreiter
11.6 Catalysis with Transition Metal Pincer Complexes 889Lukasz T. Pilarski and Kálmán J. Szabó
11.7 Biocatalysis 898Robert Kourist and Uwe T. BornscheuerReferences 922
Subpart 2: Methods 951
12 Computational Investigations into the Heck Type ReactionMechanisms 953Cai-Hong Guo and Haijun Jiao
12.1 Introduction 95312.2 Oxidative Addition 95412.3 Regioselectivity 96612.4 Stereoselectivity 97312.5 Alternative Mechanism Involving a Pd(II/IV)
Redox System 97812.6 Concluding Remarks 979
References 980
Chemical Reaction Engineering Aspects of Homogeneously CatalyzedProcesses 983Manfred Baerns and Peter Claus
13.1 Introduction 98313.2 Kinetics in Homogeneous Catalysis 98513.3 Aspects of Catalyst Recycling 99513.4 Symbols 996
References 997
13
IXContents
14 Supported Liquid Phase Catalysis 999Marco Haumann and Peter Wasserscheid
14.1 Introduction 99914.2 Support Materials 100014.3 Thin Film Coating Materials 100314.4 Summary and Outlook 1061
References 1062
15 Recent Advances in Surface Organometallic Chemistry 1069Christophe Copéret and Florent Héroguel
15.1 Introduction 106915.2 Strategy and Methods 106915.3 A Decade of Development of Single-Site Heterogeneous
Catalysts 107315.4 New Directions 107615.5 Challenges and Perspectives 1080
References 1081
16 High Throughput Screening of Homogeneous Catalysts:Selected Trends and Applications in Process Development 1085Rocco A. Paciello
16.1 Summary 1094References 1095
17 Homogeneous Photocatalysis with Organometallic Compounds 1097Norbert Hoffmann
17.1 Introduction 109717.2 Metal Carbonyl Catalyzed Reactions 109817.3 Copper (I) Catalyzed [2+2] Photocycloadditions
of Alkenes 110617.4 Photochemical Electron Transfer Mediated Reactions 110817.5 Photochemically Supported C-H Activation with Organometal
Compounds 112417.6 Conclusions 1128
References 1129
18 Electrochemical Water Oxidation and Reduction Catalyzedby Organometallic Compounds 1135Mei Wang and Fei Li
18.1 Introduction 113518.2 Electrochemical Water Oxidation to O2 Catalyzed by Organometallic
Compounds 113618.3 Electrochemical Water Reduction to H2 Catalyzed by Organometallic
Compounds 114618.4 Concluding Remarks and Outlook 1187
References 1188
ContentsX
19 Metal-Catalyzed Multicomponent Reactions 1195Jeffrey S. Quesnel and Bruce A. Arndtsen
19.1 Introduction 119519.2 Multicomponent Carbonylation Reactions 119619.3 Multicomponent Cross-Coupling Reactions 120319.4 Metallacycles in Multicomponent Reactions 121019.5 Multicomponent Approaches to 1,3-Dipolar
Cycloadditions 121519.6 Summary and Outlook 1217
References 1217
Volume 4
20 Supercritical Fluids as Advanced Media for Reaction and Separationin Homogeneous Catalysis 1221Jędrzej Walkowiak, Giancarlo Franciò, and Walter Leitner
20.1 Introduction 122120.2 Organometallic Catalysis in Supercritical Fluids 122520.3 Organometallic Catalysis in CO2-Expanded
Liquid Phases 123520.4 Supercritical CO2-Based Multiphase Systems for Continuous-Flow
Homogeneous Catalysis 123920.5 Summary and Outlook 1253
References 1253
Subpart 3: Special Reactions 1259
21 Carbonylation of Nitroarenes and Aromatic Amines 1261Marcus Harrer and Jörg Sundermeyer
21.1 Present Synthesis of Isocyanates via the Phosgene Route 126121.2 Alternative Carbonylation Strategies towards Carbonic Acid
Derivatives 126221.3 Overview 126321.4 Reductive Carbonylation of Nitroarenes 126421.5 Redox Carbonylation of Nitroarenes and Aromatic Amines According
to (21.4) and (21.5) 127421.6 Oxidative Carbonylation of Aromatic Amines According to (21.6)
and (21.7) 127521.7 Summary 1280
References 1281
22 Pauson–Khand Reaction 1287Takanori Shibata
22.1 Introduction 128722.2 Co-Catalyzed Reaction 1288
XIContents
22.3 Ti-Catalyzed Reaction 129322.4 Ru-Catalyzed Reaction 129422.5 Rh-Catalyzed Reaction 129722.6 Ir-Catalyzed Reaction 130222.7 Summary 1304
References 1304
23 C-H Activation Coupling Reactions 1307Miguel A. Esteruelas and Montserrat Oliván
23.1 Introduction 130723.2 Mechanisms of C-H Bond Activation 130823.3 Selectivity of Competitive C-H Bond Activations 130923.4 Functionalization of Alkanes and C(sp3)-H Bonds 131023.5 Aromatic C-H Transformations 131523.6 Alkylation of Nitrogen Heterocycles 132323.7 Hydroacylation of Alkenes and Alkynes 132323.8 Summary and Outlook 1327
References 1328
24 Metathesis 1333Mariusz Ke dziorek and Karol Grela
24.1 Historical Background (Introduction) 133324.2 Reaction Mechanism 133424.3 Homogeneous Catalytic Systems 133524.4 Industrial Applications 134224.5 Conclusion 1350
Acknowledgments 1350References 1350
25 The Value and Application of Transition Metal Catalyzed AlkeneIsomerization in Industry 1365Casey R. Larsen and Douglas B. Grotjahn
25.1 Introductory Remarks and Mechanistic Considerations 136525.2 Isomerization of Non-functionalized Alkenes 136725.3 Isomerization of Functionalized Alkenes 137025.4 Recent Developments 137425.5 Concluding Remarks 1375
References 1375
26 Catalysis and Scope of the Hydroamination of Non-activatedCC Multiple Bonds 1379Zhen Li and Thomas E. Müller
26.1 Introduction 137926.2 Rare-Earth and Actinide Metals as Hydroamination Catalysts 138026.3 Hydroamination Catalysts Based on Group 4/5 Metals 1390
ContentsXII
26.4 Hydroamination Catalysts Based on Alkaline-Earth Metals 139626.5 Late Transition-Metal Complexes as Homogeneous Hydroamination
Catalysts 139726.6 Heterogeneous and Immobilized Hydroamination Catalysts 140826.7 Brønsted Acid Catalyzed Hydroamination of Alkenes and Alkynes 141026.8 Base-Catalyzed Hydroamination 141226.9 Conclusions 1415
Acknowledgments 1417References 1417
27 Catalytic Amide Bond Forming Methods 1427Benjamin N. Atkinson, A. Rosie Chhatwal, and Jonathan M.J. Williams
27.1 Amidation of Carboxylic Acids 142727.2 Transamidation 143127.3 Amidation of Esters 143727.4 Amidation of Aldehydes (Without Oxime Intermediates) 144027.5 Amidation of Alcohols 144327.6 Amidation of Nitriles 144527.7 Oxime/Oxime Intermediates to Amides 144927.8 Aminocarbonylations 145227.9 Miscellaneous Amidations 145627.10 Conclusion 1457
References 1458
28 Synthesis of Heterocycles by Pd-catalyzed and Pd-catalysis InitiatedMulti-component Reactions 1463Thomas J. J. Müller
28.1 Introduction 146328.2 MCR by Insertion of Allenes 146428.3 MCR by Insertion of Carbon Monoxide 146828.4 MCR by Insertion of Alkenes and Alkynes 147028.5 MCR by Initial Sonogashira Alkynylation 147328.6 MCR by Carbonylative Sonogashira Alkynylation 147728.7 MCR by Catalytic Enamine Generation and Arylation 147828.8 Conclusion 1479
List of Abbreviations 1480Acknowledgments 1480References 1480
29 Metal-Catalyzed Baeyer–Villiger Oxidations 1485Giorgio Strukul and Alessandro Scarso
29.1 Introduction 148529.2 Oxidation of Cyclobutanones 148729.3 Oxidation of Other Ketones 149129.4 BV in Water 1497
XIII
29.5 Organic and Heterogeneous Catalysis 149829.6 Conclusions 1503
References 1504
30 Dihydroxylations of Olefins and Related Reactions 1509Sebastian Schmidt and Bernd Plietker
30.1 Introduction 150930.2 Osmium 150930.3 Ruthenium 151530.4 Iron 1521
References 1522
31 Selective Alkane Oxidation 1525Anna Company and Miquel Costas
31.1 Introduction 152531.2 Iron-Based Catalysts 152631.3 Manganese-Based Catalysts 152831.4 Chromium-Based Catalysts 153131.5 Vanadium-Based Catalysts 153231.6 Ruthenium-Based Catalysts 153331.7 Metalloporphyrins as Catalysts 153531.8 Conclusions 1538
References 1539
32 Catalytic Click Reactions 1541Sanne Schoffelen and Morten Meldal
32.1 Introduction 154132.2 Copper-Catalyzed Azide–Alkyne Cycloaddition (CuAAC) 154232.3 Effect of Substrates and Environment on the CuAAC
Reaction 154632.4 Ruthenium-Catalyzed Azide–Alkyne Cycloaddition
(RuAAC) 154832.5 Other Types of Click Reactions 1550
References 1552
33 Sulfur in Catalysis 1557Philippe Kalck
33.1 Introduction 155733.2 Sulfur as a Coordination Atom of the Ligand, or as Part of the
Ligand 156033.3 The Substrate Contains a Sulfur Atom 156933.4 Formation of Carbon-Sulfur Bonds by Catalysis 157033.5 Bioinspired Catalyst Design 157233.6 Conclusion 1573
References 1574
Contents
XIV Contents
Subpart 4: Alternative Feedstocks 1579
34 Oleochemistry 1581Andreas J. Vorholt and Arno Behr
34.1 Introduction 158134.2 Processing of Fatty Acids and Glycerol 158334.3 Conclusions 1595
References 1595
35 Homogeneous Catalysis with CO2 as a Building Block: An IndustrialPerspective 1601Thomas Schaub, Rocco A. Paciello, and Michael LimbachReferences 1612
36 The Role of Homogeneous Catalysis in the Conversion of Biomass andBiomass Derived Platform Chemicals 1615Peter J. Deuss, Katalin Barta, Sandra Hinze, and Johannes G. de Vries
36.1 Introduction 161536.2 (Hemi-)Cellulose and Sugars 161836.3 Lignin 163036.4 Oils and Fats 1636
References 1646
Subpart 5: Catalysis for Energy 1653
37 Photochemical Hydrogen Production with Earth-Abundant MetalComplexes as Molecular Catalysts 1655Mei Wang and Licheng Sun
37.1 Introduction 165537.2 Photocatalytic H2-Evolving Systems with Iron Complexes as
Catalysts 165837.3 Photocatalytic H2-Evolving Systems with Cobalt Complexes as
Catalysts 166737.4 Photocatalytic H2-Evolving Systems with a Nickel Complex as
Catalyst 168337.5 Concluding Remarks and Outlook 1684
References 1685
38 Water-Gas Shift Reaction 1689Lars-Arne Schaper, Wolfgang A. Herrmann, and Fritz E. Kühn
38.1 Introduction and Definition 168938.2 Mechanism 169038.3 Application 169238.4 Water-Gas Shift Reaction in Chemical Industry 1695
References 1697
Index 1699
XV
List of Contributors
Bruce A. ArndtsenMcGill UniversityDepartment of ChemistrySherbrooke St. W. 801MontrealQC H3A 0B4Canada
Benjamin N. AtkinsonUniversity of BathDepartment of ChemistryClaverton DownBath BA2 7AYUK
Manfred BaernsFritz-Haber Institut der MPGDept. Inorganic ChemistryFaraday-Weg 4-614195 BerlinGermany
Moritz C. BaierUniversität KonstanzFachbereich ChemieLehrstuhl für ChemischeMaterialwissenschaftenUniversitätsstr. 1078457 KonstanzGermany
Katalin BartaRijksuniversiteit GroningenStratingh Institute for ChemistryNijenborgh 49747 AG GroningenThe Netherlands
Klaus BeckerleRWTH Aachen UniversityInstitute of Inorganic ChemistryLandoltweg 152056 AachenGermany
Arno BehrTechnische Universität DortmundFachbereich Bio- und Chemie Ing.Emil-Figge-Str. 6644227 DortmundGermany
Matthias BellerLeibniz-Institut für Katalyse an derUniversität Rostock e.V. (LIKAT)Albert-Einstein-Str. 29a18059 RostockGermany
XVI List of Contributors
David E. BergbreiterTexas A&M UniversityDepartment of ChemistryP.O. Box 30012College StationTX 77842-3012USA
Hans Ulrich BlaserFurglerstrasse 109000 St. GallenSwitzerland
Armin BörnerUniversität RostockLeibniz Institut für Katalyse e.V.Albert Einstein Str. 29a18059 RostockGermany
Uwe T. BornscheuerUniversity of GreifswaldInstitute of BiochemistryDepartment of Biotechnology &Enzyme CatalysisFelix-Hausdorff-Str. 417487 GreifswaldGermany
Alexandra Grosse BöwingBayer Antwerpen NVScheldelaan 6002040 AntwerpenBelgium
Fabrizio CavaniUniversità di BolognaDipartimento di ChimicaIndustriale “Toso Montanari”Viale Risorgimento 440136 BolognaItaly
A. Rosie ChhatwalUniversity of BathDepartment of ChemistryClaverton DownBath BA2 7AYUK
Peter ClausTU DarmstadtErnst-Berl InstitutPetersenstr.2064287 DarmstadtGermany
David J. Cole-HamiltonUniversity of Saint AndrewsSchool of ChemistryPurdie BuildingSt Andrew’sFife KY17 9STUK
Anna CompanyUniversitat de GironaDepartament de QuímicaCampus Montilivi17071 GironaCataloniaSpain
Christophe CopéretETH ZürichDepartment of Chemistry andApplied BiosciencesVladimir Prelog Weg 1-58093 ZürichSwitzerland
Boy CornilsKirschgartenstr. 665719 HofheimGermany
XVIIList of Contributors
Miquel CostasUniversitat de GironaDepartament de QuímicaCampus Montilivi17071 GironaCataloniaSpain
Johannes W. de BoerCatexel B.V.BioPartner Center LeidenGalileiweg 82333 BD LeidenThe Netherlands
Johannes G. de VriesUniversity of GroningenStratingh Institute for ChemistryNijenborgh 49747 AG GroningenThe Netherlands
and
Leibniz-Institut für Katalyse e.V.Albert-Einstein-Str. 29a18059 RostockGermany
Peter J. DeussRijksuniversiteit GroningenStratingh Institute for ChemistryNijenborgh 49747 AG GroningenThe Netherlands
Eite DrentUniversity of Saint AndrewsSchool of ChemistryPurdie BuildingSt Andrew’sFife KY17 9STUK
Gwilherm EvanoLaboratoire de Chimie Organique (LCO)Avenue F.D. Roosevelt50 CP160/061050 BrusselsBelgium
Miguel A. EsteruelasUniversidad de Zaragoza - CSICDepartamento de QuímicaInorgánica - ISQCHCentro de Innovación en QuímicaAvanzada (ORFEO-CINQA)Plaza de San Franciscos/n50009 ZaragozaSpain
Giancarlo FranciòRWTH Aachen UniversityInstitut für Technische undMakromolekulare ChemieWorringerweg 252074 AachenGermany
Robert FrankeEvonik Industries AGPaul-Baumann-Str. 145772 MarlGermany
Lukas GooßenRuhr-Universität BochumLehrstuhl für Organische Chemie IZEMOS 2/27Universitätsstraße 150 44801 BochumGermany
Karol GrelaFaculty of ChemistryBiological and Chemical Research CentreUniversity of WarsawPasteura 1, 02-093 WarsawPoland
XVIII List of Contributors
Douglas B. GrotjahnSan Diego State UniversityDepartment of Chemistry andBiochemistry5500 Campanile DriveSan DiegoCA 92182-1030USA
Cai-Hong GuoShanxi Normal UniversitySchool of Chemistry and MaterialsScienceLinfen 041004China
Ronald HageCatexel B.V.BioPartner Center LeidenGalileiweg 82333 BD LeidenThe Netherlands
Frédéric HapiotUniversité d’ArtoisUMR CNRS 8181Unité de Catalyse et de Chimie duSolide (UCCS)62300 LensFrance
Marko HapkeLeibniz-Institut für Katalyse e.V. ander Universität RostockAlbert-Einstein-Str. 29a18059 RostockGermany
Marcus HarrerPhilipps-Universität MarburgFachbereich ChemieHans-Meerwein-Straße35043 MarburgGermany
Marco HaumannFriedrich-Alexander-UniversitätErlangen-NürnbergLehrstuhl für ChemischeReaktionstechnikEgerlandstr. 391058 ErlangenGermany
Florent HéroguelETH ZürichDepartment of Chemistry andApplied BiosciencesVladimir Prelog Weg 1-58093 ZürichSwitzerland
Wolfgang A. HerrmannTechnical University MunichDepartment of Chemistry andCatalysis Research CenterLichtenbergstr. 485748 GarchingGermany
Sandra HinzeLeibniz-Institut für Katalyse e.V.Albert-Einstein-Str. 29a18059 RostockGermany
Norbert HoffmannCNRSUniversité de Reims Champagne-ArdenneInstitut de Chimie Moléculaire deReims (UMR 7312)Equipe de PhotochimieUFR SciencesB.P. 103951687 ReimsFrance
XIXList of Contributors
Shingo ItoThe University of TokyoDepartment of Chemistry andBiochemistry7-3-1 HongoBunkyo-kuTokyo 113-8656Japan
Ralf JackstellUniversität RostockLeibniz-Institut für Katalyse e.V.Albert-Einstein-Str. 29a18059 RostockGermany
Haijun JiaoLeibniz-Institut für Katalyse e.V.Universität RostockAlbert-Einstein-Strasse 29a18059 RostockGermany
Reinhard JiraKabastastrasse 981243 MünchenGermany
Kathrin JungeLeibniz-Institut für Katalyse e.V. ander Universität RostockAlbert-Einstein-Str. 29a18059 RostockGermany
Philippe KalckUniversité de Toulouse UPS-INPLCCLaboratoire de Chimie deCoordination UPR CNRS 8241composante ENSIACET4 allée Emile Monso BP 4436231030 Toulouse Cedex 4France
Walter KaminskyUniversity of HamburgInstitute for Technical andMacromolecular ChemistryBundesstr. 4520146 HamburgGermany
Mariusz KędziorekFaculty of ChemistryBiological and Chemical Research CentreUniversity of WarsawPasteura 1, 02-093 WarsawPoland
Rhett KempeUniversity of BayreuthInorganic Chemistry IIUniversitätsstr. 3095440 BayreuthGermany
Oxana A. KholdeevaBoreskov Institute of Catalysis, SB RASPr. akademika Lavrentieva 5630090 NovosibirskRussia
and
Novosibirsk State UniversityPirogova str. 2630090 NovosibirskRussia
Jürgen KlankermayerRWTH Aachen UniversityInstitut für Technische undMakromolekulare Chemie (ITMC)Worringerweg 252074 AachenGermany
XX List of Contributors
Robert KouristRuhr University BochumDepartment of Biology andBiotechnologyUniversitätsstr. 15044780 BochumGermany
Karolin KralLeibniz-Institut für Katalyse e.V. ander Universität RostockAlbert-Einstein-Str. 29a18059 RostockGermany
Fritz E. KühnTechnical University MunichDepartment of Chemistry andCatalysis Research CenterLichtenbergstr. 485748 GarchingGermany
and
Technische Universität MünchenInstitute for Advanced StudyLichtenbergstraße 2a85748 GarchingGermany
Fuk Yee KwongDepartment of Applied Biology andChemical TechnologyThe Hong Kong PolytechnicUniversityHung HomKowloonHong Kong
and
Department of ChemistryThe Chinese University of HongKongShatin, NTHong Kong
Casey R. LarsenSan Diego State UniversityDepartment of Chemistry andBiochemistry5500 Campanile DriveSan DiegoCA 92182-1030USA
Walter LeitnerRWTH Aachen UniversityInstitut für Technische undMakromolekulare ChemieWorringerweg 252074 AachenGermany
Giuseppe LeoneCNR-Istituto per lo Studio delleMacromolecole (ISMAC)via E. Bassini 1520133 MilanoItaly
Fei LiDalian University of TechnologyState Key Laboratory of FineChemicalsDUT-KTH Joint Education andResearch Center on MolecularDevicesDalian 116024China
Zhen LiRWTH Aachen UniversityDepartment of ChemistryWorringerweg 252074 AachenGermany
XXI
Michael LimbachBASF SEHomogeneous CatalysisGCS/H-M31367056 LudwigshafenGermany
Gerrit A. LuinstraUniversity of HamburgInstitute for Technical andMacromolecular ChemistryBundesstr. 4520146 HamburgGermany
Hieronim MaciejewskiAdam Mickiewicz University inPoznańFaculty of ChemistryUmultowska 89B61–614 PoznańPoland
Lionel MagnaIFP Energies nouvellesEtablissement de LyonRond-pont de l’exchanger BP369360 SolaizeFrance
Christoph MalbertzRWTH Aachen UniversityInstitut für Technische undMakromolekulare Chemie (ITMC)Worringerweg 252074 AachenGermany
List of Contributors
Patrizia MamoneTechnische Universität KaiserslauternInstitut für Organische ChemieErwin-Schrödinger-Str. G.5467663 KaiserslauternGermany
Bogdan MarciniecAdam Mickiewicz University inPoznańFaculty of ChemistryUmultowska 89B61–614 PoznańPoland
and
Adam Mickiewicz University inPoznańCenter for Advanced TechnologiesUmultowska 89C61–614 PoznańPoland
Stefan MeckingUniversität KonstanzFachbereich ChemieLehrstuhl für ChemischeMaterialwissenschaftenUniversitätsstr. 1078457 KonstanzGermany
Morten MeldalUniversity of CopenhagenCenter for Evolutionary ChemicalBiology Department of ChemistryUniversitetsparken 52100 CopenhagenDenmark
XXII List of Contributors
Leslaw MleczkoBayer Technology Services GmbHKaiser-Wilhelm-Allee 751368 LeverkusenGermany
Eric MonflierUniversité d’ArtoisUMR CNRS 8181Unité de Catalyse et de Chimie duSolide (UCCS)62300 LensFrance
Bernd H. MüllerLeibniz-Institut für Katalyse e.V. ander Universität RostockAlbert-Einstein-Str. 29a18059 RostockGermany
Thomas E. MüllerRWTH Aachen UniversityDepartment of ChemistryWorringerweg 252074 AachenGermany
Thomas J. J. MüllerHeinrich-Heine-UniversitätInstitut für Organische ChemieUniversitätsstr. 140225 DüsseldorfGermany
Wolfgang MüllerLinde AGLinde Engineering DivisionDr.-Carl-von-Linde-Str. 6-1482049 PullachGermany
Helfried NeumannLeibniz-Institut für Katalyse an derUniversität Rostock e.V. (LIKAT)Albert-Einstein-Str. 29a18059 RostockGermany
Steven P. NolanGhent UniversityDepartment of Inorganic andPhysical ChemistryKrijgslaan 281, S-3Ghent 9000Belgium
Kyoko NozakiThe University of TokyoDepartment of Chemistry andBiochemistry7-3-1 HongoBunkyo-kuTokyo 113-8656Japan
Jun OkudaRWTH Aachen UniversityInstitute of Inorganic ChemistryLandoltweg 152056 AachenGermany
Montserrat OlivánUniversidad de Zaragoza - CSICDepartamento de QuímicaInorgánica - ISQCHCentro de Innovación en QuímicaAvanzada (ORFEO-CINQA)Plaza de San Franciscos/n50009 ZaragozaSpain
XXIIIList of Contributors
Hélène Olivier-BourbigouIFP Energies nouvellesEtablissement de LyonRond-pont de l’exchanger BP369360 SolaizeFrance
Rocco A. PacielloBASF SEHomogeneous CatalysisGCS/H-M31367056 LudwigshafenGermany
Walt Partenheimer7253 SW 2th AvenuePortlandOR 97219USA
Piotr Pawluc Adam Mickiewicz University inPoznańFaculty of ChemistryUmultowska 89B61–614 PoznańPoland
Stephan PeitzLeibniz-Institut für Katalyse e.V. ander Universität RostockAlbert-Einstein-Str. 29a18059 RostockGermany
Normen PeuleckeLeibniz-Institut für Katalyse e.V. ander Universität RostockAlbert-Einstein-Str. 29a18059 RostockGermany
Cezary PietraszukAdam Mickiewicz University inPoznańFaculty of ChemistryUmultowska 89B61–614 PoznańPoland
Lukasz T. PilarskiStockholm UniversityDepartment of Organic ChemistryArrhenius LabSvante Arrhenius väg 16 C106 91 StockholmSweden
Bernd PlietkerUniversität StuttgartInstitut für Organische ChemiePfaffenwaldring 5570569 StuttgartGermany
Benoît PuginSolvias AGRömerpark 2CH-4303 KaiseraugstSwitzerland
Jeffrey S. QuesnelMcGill UniversityDepartment of ChemistrySherbrooke St. W. 801MontrealQC H3A 0B4Canada
Rubén S. RamónUniversity of St AndrewsEaStCHEM School of ChemistrySt Andrews KY16 9STUK
XXIV List of Contributors
Giovanni RicciCNR-Istituto per lo Studio delleMacromolecole (ISMAC)via E. Bassini 1520133 MilanoItaly
Uwe RosenthalLeibniz-Institut für Katalyse e.V. ander Universität RostockAlbert-Einstein-Str. 29a18059 RostockGermany
Lionel A. SaudanFirmenich SA, SynthesisCorporate R&D DivisionPostfach 2391211 Genève 8Switzerland
Alessandro ScarsoUniversità Ca’ Foscari VeneziaDipartimento di Scienze Molecolarie Nanosistemivia Torino 15530170 Venezia MestreItaly
Thomas SchaubBASF SEHomogeneous CatalysisGCS/H-M31367056 LudwigshafenGermany
Lars-Arne SchaperTechnical University MunichDepartment of Chemistry andCatalysis Research CenterLichtenbergstr. 485748 GarchingGermany
Klaus SchmidOxea GmbHOtto-Roelen-Straße 346147 OberhausenGermany
Sebastian SchmidtUniversität StuttgartInstitut für Organische ChemiePfaffenwaldring 5570569 StuttgartGermany
Sanne SchoffelenUniversity of CopenhagenCenter for Evolutionary ChemicalBiology Department of ChemistryUniversitetsparken 52100 CopenhagenDenmark
Reinhard SchomäckerTU BerlinInstitut für ChemieSekr. TC 8Straβe des 17 Juni 12410623 BerlinGermany
Michael SchwarzeTU BerlinInstitut für ChemieSekr. TC 8Straβe des 17 Juni 12410623 BerlinGermany
XXVList of Contributors
Takanori ShibataWaseda UniversitySchool of Advanced Science andEngineeringDepartment of Chemistry andBiochemistryOkuboShinjukuTokyo 1698555Japan
Chau Ming SoDepartment of Applied Biology andChemical TechnologyThe Hong Kong PolytechnicUniversityHung HomKowloonHong Kong
Felix SpindlerSolvias AGRömerpark 2CH-4303 KaiseraugstSwitzerland
Bradley A. SteinhoffEastman Chemical CompanyResearch LaboratoriesPO Box 1972, KingsportTN 37662USA
Giorgio StrukulUniversità Ca’ Foscari VeneziaDipartimento di Scienze Molecolarie Nanosistemivia Torino 15530170 Venezia MestreItaly
Licheng SunDalian University of TechnologyState Key Laboratory of FineChemicalsDUT-KTH Joint Education andResearch Centre on MolecularDevicesDalian 116012China
and
KTH Royal Institute of TechnologySchool of Chemical science andEngineeringDepartment of ChemistryStockholm 10044Sweden
Jörg SundermeyerPhilipps-Universität MarburgFachbereich ChemieHans-Meerwein-Straße35043 MarburgGermany
Kálmán J. SzabóStockholm UniversityDepartment of Organic ChemistryArrhenius LabSvante Arrhenius väg 16 C106 91 StockholmSweden
Marc TailleferInstitut Charles Gerhardt8, Rue de l’Ecole Normale34 296 Montpellier Cedex 5France
Joaquim Henrique TelesBASF SEProcess Research and ChemicalEngineering67056 LudwigshafenGermany
XXVI List of Contributors
Anis TliliICBMS - SURCOOF (UMR CNRS5246 - Lyon)Universitè Claude Bernard - Lyon 143 Bd du 11 novembre 1918Bat. Raulin (4ème ètage)69622 Villeurbanne CedexFrance
Mathieu J.-L. TschanEcole Nationale Supérieure deChimie de ParisLaboratoire Charles Friedel, 11rue Pierre etMarie Curie75005 ParisFrance
Piet W.N.M. van LeeuwenLaboratoire de Physique et Chimiede Nano-Objets (LPCNO)INSA, 135 Avenue de Rangueil31077 ToulouseFrance
Alejandro Varela-FernandezDSM Innovative Synthesis B.V.P.O. Box 186160 MD GeleenThe Netherlands
Andreas J. VorholtTechnische Universität DortmundFachbereich Bio- und Chemie Ing.Emil-Figge-Str. 6644227 DortmundGermany
Jedrzej WalkowiakAdam Mickiewicz University in PoznanCentre for Advanced TechnologiesUmultowska 89c61-614 PoznanPoland
Mei WangDalian University of TechnologyState Key Laboratory of FineChemicalsDUT-KTH Joint Education andResearch Center on MolecularDevicesDalian 116024China
Peter WasserscheidFriedrich-Alexander-UniversitätErlangen-NürnbergLehrstuhl für ChemischeReaktionstechnikEgerlandstr. 391058 ErlangenGermany
Nico WedingLeibniz-Institut für Katalyse e.V. ander Universität RostockAlbert-Einstein-Str. 29a18059 RostockGermany
Ernst WiebusOxea GmbHOtto-Roelen-Str. 346147 OberhausenGermany
Gerrit WienhöferLeibniz-Institut für Katalyse e.V. ander Universität RostockAlbert-Einstein-Str. 29a18059 RostockGermany
Jonathan M.J. WilliamsUniversity of BathDepartment of ChemistryClaverton DownBath BA2 7AYUK
XXVIIList of Contributors
Anina WöhlLinde AGLinde Engineering DivisionDr.-Carl-von-Linde-Str. 6-1482049 PullachGermany
Aurel WolfBayer Technology Services GmbHKaiser-Wilhelm-Allee 751368 LeverkusenGermany
Shung Man WongDepartment of Applied Biology andChemical TechnologyThe Hong Kong PolytechnicUniversityHung HomKowloonHong Kong
Xiao-Feng WuLeibniz-Institut für Katalyse an derUniversität Rostock e.V. (LIKAT)Albert-Einstein-Str. 29a18059 RostockGermany
Baoxin ZhangUniversität RostockLeibniz Institut für Katalyse e.V.Albert Einstein Str. 29a18059 RostockGermany
Joseph R. ZoellerEastman Chemical CompanyResearch LaboratoriesPO Box 1972, KingsportTN 37662USA