Cooperative catalysis : designing efficient catalysts for synthesis
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Bibliographic Information
Cooperative catalysis : designing efficient catalysts for synthesis
Wiley-VCH Verlag GmbH & Co. KGaA, c2015
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Includes bibliographical references and index
Description and Table of Contents
Description
Written by experts in the field, this is a much-needed overview of the rapidly emerging field of cooperative catalysis.
The authors focus on the design and development of novel high-performance catalysts for applications in organic synthesis (particularly asymmetric synthesis), covering a broad range of topics, from the latest progress in Lewis acid / Br?nsted base catalysis to e.g. metal-assisted organo catalysis, cooperative metal/enzyme catalysis, and cooperative catalysis in polymerization reactions and on solid surfaces. The chapters are classified according to the type of cooperating activating groups, and describe in detail the different strategies of cooperative activation, highlighting their respective advantages and pitfalls. As a result, readers will learn about the different concepts of cooperative catalysis, their corresponding modes of operation and their applications, thus helping to find a solution to a specific synthetic catalysis problem.
Table of Contents
Preface XIII
Acknowledgments XVII
List of Contributors XIX
1 Lewis Acid-Bronsted Base Catalysis 1
Masakatsu Shibasaki and Naoya Kumagai
1.1 Introduction 1
1.2 Lewis Acid-Bronsted Base Catalysis in Metalloenzymes 1
1.3 Hard Lewis Acid-Bronsted Base Cooperative Catalysis 3
1.3.1 Cooperative Catalysts Based on a 1,1'-Binaphthol Ligand Platform 3
1.3.2 Cooperative Catalysts Based on a Salen and Schiff Base Ligand Platform 11
1.3.3 Cooperative Catalysts Based on a Ligand Platform Derived from Amino Acids 17
1.4 Soft Lewis Acid-Bronsted Base Cooperative Catalysis 21
1.5 Conclusion 24
References 25
2 Lewis Acid-Lewis Base Catalysis 35
Christina Moberg
2.1 Introduction 35
2.2 Lewis Acid and Lewis Base Activation 35
2.2.1 Modes of Activation 35
2.2.2 Self-Quenching 37
2.3 Addition to Carbonyl Compounds 38
2.3.1 Reduction of Ketones 38
2.3.2 Alkylation of Aldehydes and Ketones 39
2.3.3 Allylation of Aldehydes and Ketones 41
2.3.4 Cyanation of Aldehydes, Ketones, and Imines 43
2.4 Condensation Reactions 47
2.4.1 Aldol Reactions 47
2.4.2 Mannich Reactions 48
2.5 Morita-Baylis-Hillman Reactions 48
2.6 Epoxide Openings 50
2.6.1 Coupling with CO2 and CS2 50
2.7 Cyclization Reactions 51
2.7.1 [2+2] Cycloadditions 51
2.7.2 [3+2] Cycloadditions 56
2.7.3 [4+2] Additions 58
2.8 Polymerizations 60
2.9 Conclusions and Outlook 61
References 62
3 Cooperating Ligands in Catalysis 67
Monica Trincado and Hansjoerg Grutzmacher
3.1 Introduction 67
3.2 Chemically Active Ligands Assisting a Metal-Localized Catalytic Reaction 67
3.2.1 Cooperating Ligands with a Pendant Basic Site 67
3.2.2 Remote Pendant Basic Sites and Reorganization of Systems as Driving Forces for Metal-Ligand Cooperativity 89
3.2.3 Metal-Ligand Cooperation with a Pendant Acid Site 94
3.3 Redox-Active Ligands Assisting Metal-Based Catalysts 96
3.3.1 Redox-Active Ligands as Electron Reservoirs 96
3.3.2 Redox-Active Ligands Participating in Direct Substrate Activation 101
3.4 Summary 104
References 105
4 Cooperative Enamine-Lewis Acid Catalysis 111
HongWang and Yongming Deng
4.1 Introduction 111
4.1.1 Challenge in Combining Enamine Catalysis with Lewis Acid Catalysis 112
4.2 Reactions Developed through Cooperative Enamine-Lewis Acid Catalysis 113
4.2.1 -Alkylation of Carbonyl Compounds 114
4.2.2 Asymmetric Direct Aldol Reactions 133
4.2.3 Asymmetric Hetero-Diels-Alder Reactions 136
4.2.4 Asymmetric Michael Addition Reactions 138
4.3 Conclusion 139
Acknowledgment 140
References 140
5 Hydrogen Bonding-Mediated Cooperative Organocatalysis by Modified Cinchona Alkaloids 145
Xiaojie Lu and Li Deng
5.1 Introduction 145
5.2 The Emergence of Highly Enantioselective Base Organocatalysis 145
5.3 Hydrogen Bonding-Based Cooperative Catalysis by Modified Cinchona Alkaloids 151
5.3.1 The Emergence of Modified Cinchona Alkaloids as Bifunctional Catalysts 151
5.3.2 The Development of Modified Cinchona Alkaloids as Broadly Effective Bifunctional Catalysts 153
5.3.3 Multifunctional Cooperative Catalysis by Modified Cinchona Alkaloids 159
5.3.4 Selective Examples of Synthetic Applications 164
5.4 Conclusion and Outlooks 167
Acknowledgments 167
References 167
6 Cooperation of Transition Metals and Chiral Bronsted Acids in Asymmetric Catalysis 171
HuaWu, Yu-PingHe, and Liu-ZhuGong
6.1 General Introduction 171
6.2 Cooperative Catalysis of Palladium(II) and a Bronsted Acid 172
6.3 Cooperative Catalysis of Palladium(0) and a Bronsted Acid 175
6.4 Cooperative Catalysis of a Rhodium Complex and a Bronsted Acid 179
6.5 Cooperative Catalysis of a Silver Complex and a Bronsted Acid 187
6.6 Cooperative Catalysis of a Copper Complex and a Bronsted Acid 188
6.7 Cooperative Catalysis of an Iridium Complex and a Bronsted Acid 189
6.8 Cooperative Catalysis of an Iron Complex and a Bronsted Acid 191
6.9 Perspective 193
References 193
7 Cooperative Catalysis Involving Chiral Ion Pair Catalysts 197
MarioWaser, Johanna Novacek, and Katharina Gratzer
7.1 Introduction 197
7.2 Chiral Cation-Based Catalysis 198
7.2.1 Cooperative Combination of Chiral Cation-Based Catalysts and Transition-Metal Catalysts 199
7.2.2 Bifunctional Chiral Cation-Based Catalysts 200
7.2.3 Chiral Cation-Based Catalysts Containing a Catalytically Relevant Achiral Counteranion 212
7.3 Chiral Anion Based Catalysis 216
7.3.1 Cooperative Organocatalytic Approaches Involving a Chiral Anion in Ion-Pairing Catalysts 216
7.3.2 Chiral Anion Catalysis in Combination with Metal Catalysis 217
7.3.3 Cooperative Use of H-Bonding Catalysts for Anion Binding and Complementary Activation Modes 220
7.4 Synopsis 221
References 222
8 Bimetallic Catalysis: Cooperation of CarbophilicMetal Centers 227
MarcelWeiss and Rene Peters
8.1 Introduction 227
8.2 Homobimetallic Catalysts 228
8.2.1 Cooperation of Two Palladium Centers 228
8.2.2 Cooperation of Two Gold Centers 238
8.2.3 Cooperation of Two Nickel Centers 242
8.2.4 Cooperation of Two Rh or Ir Centers 243
8.3 Heterobimetallic Catalysts 246
8.3.1 Cooperation of a Pd Center with a Different Metal Center 246
8.3.2 Cooperation of a Ni Center with another Metal Center 255
8.3.3 Cooperation of a Cu or Ag Center with another Metal Center (Not Pd) 257
8.4 Synopsis 258
Acknowledgments 259
References 259
9 Cooperative H2 Activation by Borane-Derived Frustrated Lewis Pairs 263
Jan Paradies
9.1 Introduction 263
9.2 Mechanistic Considerations 264
9.3 General Considerations 267
9.3.1 Choice of Lewis Base 267
9.3.2 Choice of Lewis Acid 268
9.3.3 Intramolecular Frustrated Lewis Pairs 270
9.4 Hydrogenation of Imines 273
9.5 Hydrogenation of Enamines and Silylenol Ethers 276
9.6 Hydrogenation of Heterocycles 279
9.7 Hydrogenation of Enones, Alkylidene Malonates, and Nitroolefins 282
9.8 Hydrogenation of Unpolarized Olefins and Polycyclic Aromatic Hydrocarbons 286
9.9 Summary 290
Abbreviations 290
References 291
10 Catalysis by Artificial Oligopeptides 295
Fabrizio Mancin, Leonard J. Prins, and Paolo Scrimin
10.1 Cooperative Catalysis by Short Peptides 295
10.1.1 Unstructured Sequences 295
10.1.2 Structured Sequences 299
10.2 Cooperative Catalysis by Supramolecular Systems 307
10.2.1 Unimolecular Receptors/Catalysts 307
10.2.2 Molecular Aggregates 309
10.3 Cooperative Catalysis by Nanosystems 312
10.3.1 Dendrimer-Based Catalysts 312
10.3.2 Nanoparticle-Based Catalysts 315
10.4 Conclusions 320
References 321
11 Metals and Metal Complexes in Cooperative Catalysis with Enzymes within Organic-Synthetic One-Pot Processes 325
Harald Groeger
11.1 Introduction 325
11.2 Metal-Catalyzed In situ-Preparation of an Enzyme's Reagent (Cofactor) Required for the Biotransformation 328
11.2.1 Overview About the Concept of In situ-Cofactor Recycling in Enzymatic Redox Processes 328
11.2.2 Metal-Catalyzed In situ-Recycling of Reduced Cofactors NAD(P)H for Enzymatic Reduction Reactions 330
11.2.3 Metal-Catalyzed In situ-Recycling of Oxidized Cofactors NAD(P)+ for Enzymatic Oxidation Reactions 331
11.3 Combination of a Metal-Catalyzed Racemization of a Substrate with a Stereoselective Biotransformation Toward a Dynamic Kinetic Resolution 332
11.3.1 Dynamic Kinetic Resolution Based on Metal-Catalyzed Racemization of the Substrate in Combination with Enzymatic Resolution in Aqueous Media 332
11.3.2 Dynamic Kinetic Resolution Based on Metal-Catalyzed Racemization of the Substrate in Combination with Enzymatic Resolution in Organic Media 334
11.4 Combinations of Metal Catalysis and Biocatalysis Toward "Consecutive" One-Pot Processes without Intermediate Isolation 339
11.4.1 Introduction of the Concepts of "Consecutive" One-Pot Processes without Intermediate Isolation 339
11.4.2 "Consecutive" One-Pot Processes Running in a Tandem-Mode 339
11.4.3 "Consecutive" One-Pot Processes with Completion of the Initial Reaction Prior to Catalyst Addition for the Second Step 343
11.5 Summary and Outlook 347
References 347
12 Cooperative Catalysis on Solid Surfaces versus SolubleMolecules 351
Michael M. Nigra and Alexander Katz
12.1 Introduction 351
12.2 Tuning Cooperativity of Acid-Base Bifunctional Groups by Varying the Distance Between Them in a Soluble-Molecule Platform 352
12.3 Acid-Base Bifunctional Catalysts on Two-Dimensional Surfaces: Organic-Inorganic Materials 356
12.4 Cooperative Catalysis on Surfaces versus Soluble Molecular Platforms for Kinetic Resolution of Racemic Epoxides 362
12.5 Depolymerization of Biomass Polymers via Cooperative Catalysis on Surfaces 365
12.6 Conclusions 370
References 370
13 Cooperative Catalysis in Polymerization Reactions 373
MalteWinnacker, Sergei Vagin, and Bernhard Rieger
13.1 Introduction 373
13.2 Cooperative Effects for the Polymerization of Lactide and Other Cyclic Esters 374
13.3 Polymerization Reactions of Vinyl Monomers with Frustrated Lewis Pairs 385
13.4 Zinc-Based Cooperative Catalysis of Epoxide/CO2 Copolymerization 390
13.5 Cooperative Mechanism of Epoxide/CO2 Copolymerization by Salen-Type Complexes 402
13.6 Summary 413
References 414
Index 417
by "Nielsen BookData"
