Iron Catalysis in Organic Chemistry Reactions and Applications
by Plietker, BerndEdition: 1st
Format: Hardcover
Pub. Date: 2008-09-22
Publisher(s): Wiley-VCH
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Summary
This first comprehensive book to cover this exciting field also deals with the biological aspects, such as enzymes with iron.Following an introduction, this handy reference and handbook goes on to deal with reductions, oxidations of C, H- and C=C bonds, oxidative allylic oxygenation and amination, the oxidation of heteroatoms, cross coupling reactions, aromatic and nucleophilic substitutions, addition to carbonyl compounds, and cyclisations as well as ring opening reactions.The chapters are clearly classified according to the reaction type, allowing readers to quickly locate the desired information.
Author Biography
Bernd Plietker, born in Gronau (Germany) in 1971, studied chemistry in M++nster and Dresden. In 1999 he received his PhD under the guidance of Peter Metz at the University of Dresden. After postdoctoral stays in the group of Jan-Erling B+ñckvall (Stockholm) and Barry Trost (Stanford) he began his independent research career associated with Norbert Krause (Dortmund). In 2007 he became a Professor of Organic Chemistry at the University of Stuttgart. His research interests include the development of sustainable metal catalysis (based on ruthenium or iron complexes) and their application in the total synthesis of natural products or natural product like libraries.
He has received a Liebig fellowship and the Award of the Otto-Roehm Gedaechtnisstiftung.
He has received a Liebig fellowship and the Award of the Otto-Roehm Gedaechtnisstiftung.
Table of Contents
| Preface | p. XI |
| List of Contributors | p. XIII |
| Iron Complexes in Organic Chemistry | p. 1 |
| Introduction | p. 1 |
| General Aspects of Iron Complex Chemistry | p. 2 |
| Electronic Configuration, Oxidation States, Structures | p. 2 |
| Fundamental Reactions | p. 2 |
| Organoiron Complexes and Their Applications | p. 4 |
| Binary Carbonyl-Iron Complexes | p. 5 |
| Alkene-Iron Complexes | p. 7 |
| Allyl- and Trimethylenemethane-Iron Complexes | p. 8 |
| Acyl- and Carbene-Iron Complexes | p. 9 |
| Diene-Iron Complexes | p. 11 |
| Ferrocenes | p. 18 |
| Arene-Iron Complexes | p. 18 |
| Catalysis Using Iron Complexes | p. 20 |
| Iron Complexes as Substrates and/or Products in Catalytic Reactions | p. 20 |
| Iron Complexes as Ligands for Other Transition Metal Catalysts | p. 21 |
| Iron Complexes as Catalytically Active Species | p. 21 |
| References | p. 24 |
| Iron Catalysis in Biological and Biomimetic Reactions | p. 29 |
| Non-heme Iron Catalysts in Biological and Biomimetic Transformations | p. 29 |
| Introduction: Iron in Biological Processes | p. 29 |
| Non-heme Iron Proteins | p. 30 |
| Mononuclear Iron Sites | p. 30 |
| Dinuclear Iron Sites | p. 39 |
| Summary | p. 45 |
| References | p. 46 |
| Organic Reactions Catalyzed by Heme Proteins | p. 48 |
| Classification and General Reactivity Schemes of Heme Proteins Used in Organic Synthesis | p. 48 |
| Organic Reactions Catalyzed by Cytochromes P450 | p. 51 |
| Organic Reactions Catalyzed by Heme Peroxidases | p. 56 |
| Dehydrogenations ("Peroxidase Reactivity") | p. 56 |
| Sulfoxidations ("Peroxygenase Reactivity") | p. 57 |
| Peroxide Disproportionation ("Catalase Reactivity") | p. 58 |
| Halogenation ("Haloperoxidase Reactivity") | p. 61 |
| Epoxidations ("Monoxygenase Activity") | p. 62 |
| References | p. 66 |
| Iron-catalyzed Oxidation Reactions | p. 73 |
| Oxidations of C-H and C=C Bonds | p. 73 |
| Gif Chemistry | p. 73 |
| Alkene Epoxidation | p. 80 |
| Alkene Dihydroxylation | p. 82 |
| The Kharasch Reaction and Related Reactions | p. 84 |
| Aziridination and Diamination | p. 87 |
| References | p. 89 |
| Oxidative Allylic Oxygenation and Amination | p. 92 |
| Introduction | p. 92 |
| Iron-catalyzed Allylic Oxidations | p. 93 |
| Simple Iron Salts | p. 93 |
| Fe(III) Complexes with Bidentate Ligands | p. 94 |
| Fe[superscript 3+]/Fe[superscript 2+] Porphyrin and Phthalocyanine Complexes | p. 95 |
| Iron(III) Salen Complexes | p. 100 |
| Non-heme Iron Complexes with Tetra- and Pentadentate Ligands | p. 100 |
| Oxidative Allylic Aminations | p. 103 |
| Conclusion | p. 107 |
| References | p. 107 |
| Oxidation of Heteroatoms (N and S) | p. 109 |
| Oxidation of Nitrogen Compounds | p. 109 |
| Oxidation of Hydroxylamines to Nitroso Compounds | p. 109 |
| Oxidation of Arylamines | p. 110 |
| Other N-Oxidations | p. 110 |
| Oxidation of Sulfur Compounds | p. 111 |
| Oxidation of Thiols to Disulfides | p. 111 |
| Oxidation of Sulfides | p. 113 |
| Oxidative Imination of Sulfur Compounds | p. 119 |
| References | p. 122 |
| Reduction of Unsaturated Compounds with Homogeneous Iron Catalysts | p. 125 |
| Introduction | p. 125 |
| Hydrogenation of Carbonyl Compounds | p. 125 |
| Hydrogenation of Carbon-Carbon Double Bonds | p. 129 |
| Hydrogenation of Imines and Similar Compounds | p. 136 |
| Catalytic Hydrosilylations | p. 136 |
| Conclusion | p. 141 |
| References | p. 142 |
| Iron-catalyzed Cross-coupling Reactions | p. 147 |
| Introduction | p. 147 |
| Cross-coupling Reactions of Alkenyl Electrophiles | p. 147 |
| Cross-coupling Reactions of Aryl Electrophiles | p. 154 |
| Cross-coupling Reactions of Alkyl Electrophiles | p. 161 |
| Cross-coupling Reactions of Acyl Electrophiles | p. 168 |
| Iron-catalyzed Carbometallation Reactions | p. 170 |
| Conclusion | p. 172 |
| References | p. 173 |
| Iron-catalyzed Aromatic Substitutions | p. 177 |
| General Aspects | p. 177 |
| Electrophilic Aromatic Substitutions | p. 178 |
| Halogenation Reactions | p. 178 |
| Nitration Reactions | p. 179 |
| Sulfonylation Reactions | p. 180 |
| Friedel-Crafts Acylations | p. 181 |
| Friedel-Crafts Alkylations | p. 183 |
| Alkylation with Alcohols, Ethers and Esters | p. 184 |
| Alkylation with Alkenes | p. 186 |
| Nucleophilic Aromatic Substitutions | p. 188 |
| References | p. 191 |
| Iron-catalyzed Substitution Reactions | p. 197 |
| Introduction | p. 197 |
| Iron-catalyzed Nucleophilic Substitutions | p. 197 |
| Nucleophilic Substitutions of Non-activated C-X Bonds | p. 197 |
| Introduction | p. 197 |
| Nucleophilic Substitutions Using Lewis Acidic Fe Catalysts | p. 198 |
| Substitutions Catalyzed by Ferrate Complexes | p. 199 |
| Nucleophilic Substitution of Allylic and Propargylic C-X Bonds | p. 202 |
| Reactions Catalyzed by Lewis Acidic Fe Salts | p. 202 |
| Nucleophilic Substitutions Involving Ferrates | p. 205 |
| Conclusion | p. 213 |
| References | p. 214 |
| Addition and Conjugate Addition Reactions to Carbonyl Compounds | p. 217 |
| Introduction | p. 217 |
| Additions to Aldehydes and Ketones | p. 218 |
| Oxygen Nucleophiles | p. 218 |
| Carbon Nucleophiles | p. 219 |
| Additions to Imines and Iminium Ions | p. 223 |
| Additions to Carboxylic Acids and Their Derivatives | p. 224 |
| Oxygen Nucleophiles | p. 224 |
| Carbon Nucleophiles | p. 225 |
| Conjugate Addition to [alpha],[beta]-Unsaturated Carbonyl Compounds | p. 226 |
| Carbon Nucleophiles | p. 226 |
| Michael Reactions | p. 226 |
| Vinylogous Michael Reactions | p. 230 |
| Asymmetric Michael Reactions | p. 232 |
| Michael Reactions in Ionic Liquids and Heterogeneous Catalysis | p. 233 |
| Nitrogen Nucleophiles | p. 235 |
| Synthesis of Heterocycles | p. 236 |
| Pyridine and Quinoline Derivatives | p. 236 |
| Pyrimidine and Pyrazine Derivatives | p. 238 |
| Benzo- and Dibenzopyrans | p. 238 |
| References | p. 239 |
| Iron-catalyzed Cycloadditions and Ring Expansion Reactions | p. 245 |
| Introduction | p. 245 |
| Cycloisomerization and Alder-Ene Reaction | p. 245 |
| [2+1]-Cycloadditions | p. 249 |
| Iron-catalyzed Aziridine Formation | p. 249 |
| Iron-catalyzed Epoxide Formation | p. 251 |
| Iron-catalyzed Cyclopropane Formation | p. 252 |
| [2+2]-Cycloaddition | p. 254 |
| [4+1]-Cycloadditions | p. 256 |
| [4+2]-Cycloadditions | p. 257 |
| Diels-Alder Reactions with Normal Electron Demand | p. 257 |
| Diels-Alder Reactions with Neutral Electron Demand | p. 259 |
| Diels-Alder Reactions with Inverse Electron Demand | p. 260 |
| Cyclotrimerization | p. 260 |
| [3+2]-Cycloadditions | p. 262 |
| [3+3]-Cycloadditions | p. 263 |
| Ring Expansion Reactions | p. 263 |
| Conclusion | p. 266 |
| References | p. 266 |
| Index | p. 271 |
| Table of Contents provided by Ingram. All Rights Reserved. |
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