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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2018 Wiley-VCH Verlag GmbH & Co. KGaA,Boschstr. 12, 69469 Weinheim, Germany

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Printed on acid-free paper

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