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More About This Title Organic Synthesis Using Transition Metals 2e
English
Organic Synthesis Using Transition Metals, 2nd Edition considers the ways in which transition metals, as catalysts and reagents, can be used in organic synthesis, both for pharmaceutical compounds and for natural products. It concentrates on the bond-forming reactions that set transition metal chemistry apart from "classical" organic chemistry. Each chapter is extensively referenced and provides a convenient point of entry to the research literature. Topics covered include:
- introduction to transition metals in organic synthesis
- coupling reactions
- C-H activation
- carbonylative coupling reactions
- alkene and alkyne insertion reactions
- electrophilic alkene and alkyne complexes
- reactions of alkyne complexes
- carbene complexes
- h3- orp-allyl -allyl complexes
- diene, dienyl and arene complexes
- cycloaddition and cycloisomerisation reactions
For this second edition the text has been extensively revised and expanded to reflect the significant improvements and advances in the field since the first edition, as well as the large number of new transition metal-catalysed processes that have come to prominence in the last 10 years – for example the extraordinary progress in coupling reactions using “designer” ligands, catalysis using gold complexes, new opportunities arising from metathesis chemistry, and C-H activation – without neglecting the well established chemistry of metals such as palladium.
Organic Synthesis Using Transition Metals, 2nd Edition will find a place on the bookshelves of advanced undergraduates and postgraduates working in organic synthesis, catalysis, medicinal chemistry and drug discovery. It is also useful for practising researchers who want to refresh and enhance their knowledge of the field.
English
Roderick Bates Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore
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About the Author xiii
Preface xv
1 Introduction 1
1.1 The Basics 2
1.2 The Basic Structural Types 2
1.3 Just How Many Ligands Can Fit around a Metal Atom? 10
1.4 Mechanism and the Basic Reaction Steps 13
1.5 Catalysis 17
References 19
2 Coupling Reactions 21
2.1 Carbon–Carbon Bond Formation 21
2.2 Lithium and Magnesium: Kumada Coupling 27
2.3 Zinc: The Negishi Reaction 32
2.4 Aluminium and Zirconium 35
2.5 Tin: The Stille Reaction 37
2.6 Boron: The Suzuki Reaction 46
2.7 Silicon: The Hiyama Reaction 57
2.8 Copper: The Sonogashira Reaction 61
2.9 Other Metals 67
2.10 Homocoupling 67
2.11 Enolate and Phenoxide Coupling 69
2.12 Heteroatom Coupling 70
References 82
3 C–H Activation 89
3.1 Arenes and Heteroarenes 91
3.2 Aldehydes 100
3.3 Borylation and Silylation 102
3.4 Allylic Functionalization 103
3.5 Unfunctionalized C–H Bonds 105
References 115
4 Carbonylation 117
4.1 Carbonylative Coupling Reactions: Synthesis of Carbonyl Derivatives 117
4.2 Carbonylative Coupling Reactions: Synthesis of Carboxylic Acid Derivatives 122
4.3 Carbonylation of Alkenes and Alkynes 127
4.4 Hydroformylation 130
4.5 Stoichiometric Carbonylation Using Carbonyl Complexes 139
4.6 Carboxylation 146
4.7 Decarbonylation and Decarboxylation 148
References 150
5 Alkene and Alkyne Insertion Reactions 153
5.1 The Heck Reaction 153
5.2 Insertion Reactions Involving Zirconium and Titanium 175
References 188
6 Electrophilic Alkene and Alkyne Complexes 191
6.1 Electrophilic Palladium Complexes 191
6.2 Other Metals: Silver, Gold, Platinum and Rare Earths 210
6.3 Iron 229
6.4 Cobaloxime _-Cations 235
References 237
7 Reactions of Alkyne Complexes 241
7.1 Alkyne Cobalt Complexes 241
7.2 Propargyl Cations: The Nicholas Reaction 244
7.3 The Pauson–Khand Reaction 246
7.4 Synthesis Using Multiple Cobalt Reactions 250
References 251
8 Carbene Complexes 253
8.1 Fischer Carbenes 253
8.2 Vinylidene Complexes 269
8.3 Metathesis Reactions Involving Carbene Complexes 273
8.4 Carbyne Complexes 310
8.5 Carbene Complexes from Diazo Compounds 312
References 319
9η3- orπ-Allyl Complexes 325
9.1 Stoichiometric Reactions of π-Allyl Complexes 325
9.2 Catalysis: Mostly Palladium 328
9.3 Propargyl Compounds 357
References 357
10 Diene, Dienyl and Arene Complexes 361
10.1 η4-Diene Complexes 361
10.2 η5-Dienyl Complexes 371
10.3 η6-Arene Complexes 377
10.4 η2-Arene Complexes 387
References 389
11 Cycloaddition and Cycloisomerization Reactions 391
11.1 Formal Six-Electron, Six-Atom Cycloadditions 391
11.2 Cycloadditions Involving Fewer than Six Atoms 402
11.3 Cycloadditions Involving More than Six Atoms 407
11.4 Isomerization 414
11.5 Cycloisomerization and Related Reactions 415
References 426
Abbreviations 431
Index of Principle Transition Metal Catalysts and Reagents 433
Index 437
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“In conclusion, this is an outstanding book which should be of value to all process chemists, as well as to postgraduate students.” (Organic Process Research & Development Journal, 1 April 2013)
“This fine work, which includes an excellent bibliography, in the field of catalysis will be useful for professional chemists; it also will be a valuable resource for graduate students. Highly recommended. Graduate students, researchers/faculty, and professionals/practitioners.” (Choice, 1 December 2012)
