Iron catalysis in organic chemistry: reactions and applications
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Sprache: | English |
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Weinheim
WILEY-VCH
2008
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Online-Zugang: | Inhaltstext Inhaltsverzeichnis |
Beschreibung: | XV, 279 S. graph. Darst. |
ISBN: | 9783527319275 3527319271 |
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Contents
Preface XI
List of Contributors XIII
1 Iron Complexes in Organic Chemistry 1
Ingmar Bauer and Hans-Joachim Knölker
1.1 Introduction 1
1.2 General Aspects of Iron Complex Chemistry 2
1.2.1 Electronic Configuration, Oxidation States, Structures 2
1.2.2 Fundamental Reactions 2
1.3 Organoiron Complexes and Their Applications 4
1.3.1 Binary Carbonyl-Iron Complexes 5
1.3.2 Alkene-Iron Complexes 7
1.3.3 Allyl- and Trimethylenemethane-Iron Complexes 8
1.3.4 Acyl- and Carbene-Iron Complexes 9
1.3.5 Diene-Iron Complexes 11
1.3.6 Ferrocenes 18
1.3.7 Arene-Iron Complexes 18
1.4 Catalysis Using Iron Complexes 20
1.4.1 Iron Complexes as Substrates and/or Products in Catalytic
Reactions 20
1.4.2 Iron Complexes as Ligands for Other Transition Metal Catalysts 21
1.4.3 Iron Complexes as Catalytically Active Species 21
References 24
2 Iron Catalysis in Biological and Biomimetic Reactions 29
2.1 Non-heme Iron Catalysts in Biological and Biomimetic
Transformations 29
Jens Müller
2.1.1 Introduction: Iron in Biological Processes 29
2.1.2 Non-heme Iron Proteins 30
2.1.2.1 Mononudear Iron Sites 30
2.1.2.2 Dinudear Iron Sites 39
2.1.3 Summary 45
References 46
2.2 Organic Reactions Catalyzed by Heme Proteins 48
Martin Bröring
2.2.1 Classification and General Reactivity Schemes of Heme Proteins
Used in Organic Synthesis 48
2.2.2 Organic Reactions Catalyzed by Cytochromes P450 51
2.2.3 Organic Reactions Catalyzed by Heme Peroxidases 56
2.2.3.1 Dehydrogenations ("Peroxidase Reactivity") 56
2.2.3.2 Sulfoxidations ("Peroxygenase Reactivity") 57
2.2.3.3 Peroxide Disproportionation ("Catalase Reactivity") 58
2.2.3.4 Halogenation ("Haloperoxidase Reactivity") 61
2.2.3.5 Epoxidations ("Monoxygenase Activity") 62
References 66
3 Iron-catalyzed Oxidation Reactions 73
3.1 Oxidations of C-H and C=C Bonds 73
Agathe Christine Mayer and Carsten Bolm
3.1.1 Gif Chemistry 73
3.1.2 Alkene Epoxidation 80
3.1.3 Alkene Dihydroxylation 82
3.1.4 The Kharasch Reaction and Related Reactions 84
3.1.5 Aziridination and Diamination 87
References 89
3.2 Oxidative Allylic Oxygénation and Amination 92
Sabine Laschat, Volker Rabe, and Angelika Baro
3.2.1 Introduction 92
3.2.2 Iron-catalyzed Allylic Oxidations 93
3.2.2.1 Simple Iron Salts 93
3.2.2.2 Fe(III) Complexes with Bidentate Iigands 94
3.2.2.3 Fe3+/Fe2+ Porphyrin and Phthalocyanine Complexes 95
3.2.2.4 Iron(III) Salen Complexes 100
3.2.2.5 Non-heme Iron Complexes with Terra- and Pentadentate
Iigands 100
3.2.3 Oxidative Allylic Animations 103
3.2.4 Conclusion 107
References 107
3.3 Oxidation of Heteroatoms (N and S) 109
Olga García Manchem and Carsten Bolm
3.3.1 Oxidation of Nitrogen Compounds 109
3.3.1.1 Oxidation of Hydroxylamines to Nitroso Compounds 109
3.3.1.2 Oxidation of Arylamines 110
3.3.1.3 Other N-Oxidations 110
3.3.2 Oxidation of Sulfur Compounds 111
3.3.2.1 Oxidation of Thiols to Disulfides 111
3.3.2.2 Oxidation of Sulfides 113
3.3.2.3 Oxidative Imination of Sulfur Compounds 119
References 122
4 Reduction of Unsaturated Compounds with Homogeneous
Iron Catalysts 125
Stephan Enthaler, Kathrin Junge, and Matthias Belter
4.1 Introduction 125
4.2 Hydrogénation of Carbonyl Compounds 125
4.3 Hydrogénation of Carbon-Carbon Double Bonds 129
4.4 Hydrogénation of Imines and Similar Compounds 136
4.5 Catalytic Hydrosilylations 136
4.6 Conclusion 141
References 142
5 Iron-catalyzed Cross-coupling Reactions 147
Andreas Leaner
5.1 Introduction 147
5.2 Cross-coupling Reactions of Alkenyl Electrophiles 147
5.3 Cross-coupling Reactions of Aryl Electrophiles 154
5.4 Cross-coupling Reactions of Alkyl Electrophiles 161
5.5 Cross-coupling Reactions of Acyl Electrophiles 168
5.6 Iron-catalyzed Carbometallation Reactions 170
5.7 Conclusion 172
References 173
6 Iron-catalyzed Aromatic Substitutions 177
Jette Kischel, Kristin Mertins, Irina Jovel, Alexander Zapf, and Matthias Beller
6.1 General Aspects 177
6.2 Electrophilic Aromatic Substitutions 178
6.2.1 Halogenation Reactions 178
6.2.2 Nitration Reactions 179
6.2.3 Sulfonylation Reactions 180
6.2.4 Friedel-Crafts Acylations 181
6.2.5 Friedel-Crafts Alkylations 183
6.2.5.1 Alkylation with Alcohols, Ethers and Esters 184
6.2.5.2 Alkylation with Alkenes 186
6.3 Nudeophilic Aromatic Substitutions 188
References 191
7 Iron-catalyzed Substitution Reactions 197
Bernd Plietker
7.1 Introduction 197
7.2 Iron-catalyzed Nudeophilic Substitutions 297
7.2.1 Nudeophilic Substitutions of Non-activated C-X Bonds 197
7.2.1.1 Introduction 197
7.2.1.2 Nudeophilic Substitutions Using Lewis Acidic Fe Catalysts 198
7.2.1.3 Substitutions Catalyzed by Ferrate Complexes 199
7.2.2 Nudeophilic Substitution of Allylic and Propargylic C-X Bonds 202
7.2.2.1 Reactions Catalyzed by Lewis Acidic Fe Salts 202
7.2.2.2 Nudeophilic Substitutions Involving Ferrates 205
7.3 Condusion 213
References 234
8 Addition and Conjugate Addition Reactions to Carbonyl
Compounds 217
Jens Christoffers, Herbert Frey, and Anna Rosiak
8.1 Introduction 217
8.2 Additions to Aldehydes and Ketones 218
8.2.1 Oxygen Nudeophiles 218
8.2.2 Carbon Nudeophiles 219
8.3 Additions to Imines and Iminium Ions 223
8.4 Additions to Carboxylic Acids and Their Derivatives 224
8.4.1 Oxygen Nudeophiles 224
8.4.2 Carbon Nudeophiles 225
8.5 Conjugate Addition to oc,ß-Unsaturated Carbonyl
Compounds 226
8.5.1 Carbon Nudeophiles 226
8.5.1.1 Michael Reactions 226
8.5.1.2 Vinylogous Michael Reactions 230
8.5.1.3 Asymmetric Michael Reactions 232
8.5.1.4 Michael Reactions in Ionic Liquids and Heterogeneous
Catalysis 233
8.5.2 Nitrogen Nudeophiles 235
8.6 Synthesis of Heterocycles 236
8.6.1 Pyridine and Quinoline Derivatives 236
8.6.2 Pyrimidine and Pyrazine Derivatives 238
8.6.3 Benzo- and Dibenzopyrans 238
References 239
9 Iron-catalyzed Cycloadditions and Ring Expansion Reactions 245
Gerhard Hilt and Judith Janikowski
9.1 Introduction 245
9.2 Cydoisomerization and Alder-Ene Reaction 245
9.3 [2+l]-Cydoadditions 249
9.3.1 Iron-catalyzed Aziridine Formation 249
9.3.2 Iron-catalyzed Epoxide Formation 251
9.3.3 Iron-catalyzed Cyclopropane Formation 252
9.4 [2+2]-Cydoaddition 254
9.5 [4+l]-Cydoadditions 256
9.6 [4+2]-Cydoadditions 257
9.6.1 Diels-Alder Reactions with Normal Electron Demand 257
9.6.2 Diels-Alder Reactions with Neutral Electron Demand 259
9.6.3 Diels-Alder Reactions with Inverse Electron Demand 260
9.7 Cydotrimerization 260
9.8 [3+2]-Cydoadditions 262
9.9 [3+3]-Cydoadditions 263
9.10 Ring Expansion Reactions 263
9.11 Condusion 266
References 266
Index 271 |
adam_txt |
Contents
Preface XI
List of Contributors XIII
1 Iron Complexes in Organic Chemistry 1
Ingmar Bauer and Hans-Joachim Knölker
1.1 Introduction 1
1.2 General Aspects of Iron Complex Chemistry 2
1.2.1 Electronic Configuration, Oxidation States, Structures 2
1.2.2 Fundamental Reactions 2
1.3 Organoiron Complexes and Their Applications 4
1.3.1 Binary Carbonyl-Iron Complexes 5
1.3.2 Alkene-Iron Complexes 7
1.3.3 Allyl- and Trimethylenemethane-Iron Complexes 8
1.3.4 Acyl- and Carbene-Iron Complexes 9
1.3.5 Diene-Iron Complexes 11
1.3.6 Ferrocenes 18
1.3.7 Arene-Iron Complexes 18
1.4 Catalysis Using Iron Complexes 20
1.4.1 Iron Complexes as Substrates and/or Products in Catalytic
Reactions 20
1.4.2 Iron Complexes as Ligands for Other Transition Metal Catalysts 21
1.4.3 Iron Complexes as Catalytically Active Species 21
References 24
2 Iron Catalysis in Biological and Biomimetic Reactions 29
2.1 Non-heme Iron Catalysts in Biological and Biomimetic
Transformations 29
Jens Müller
2.1.1 Introduction: Iron in Biological Processes 29
2.1.2 Non-heme Iron Proteins 30
2.1.2.1 Mononudear Iron Sites 30
2.1.2.2 Dinudear Iron Sites 39
2.1.3 Summary 45
References 46
2.2 Organic Reactions Catalyzed by Heme Proteins 48
Martin Bröring
2.2.1 Classification and General Reactivity Schemes of Heme Proteins
Used in Organic Synthesis 48
2.2.2 Organic Reactions Catalyzed by Cytochromes P450 51
2.2.3 Organic Reactions Catalyzed by Heme Peroxidases 56
2.2.3.1 Dehydrogenations ("Peroxidase Reactivity") 56
2.2.3.2 Sulfoxidations ("Peroxygenase Reactivity") 57
2.2.3.3 Peroxide Disproportionation ("Catalase Reactivity") 58
2.2.3.4 Halogenation ("Haloperoxidase Reactivity") 61
2.2.3.5 Epoxidations ("Monoxygenase Activity") 62
References 66
3 Iron-catalyzed Oxidation Reactions 73
3.1 Oxidations of C-H and C=C Bonds 73
Agathe Christine Mayer and Carsten Bolm
3.1.1 Gif Chemistry 73
3.1.2 Alkene Epoxidation 80
3.1.3 Alkene Dihydroxylation 82
3.1.4 The Kharasch Reaction and Related Reactions 84
3.1.5 Aziridination and Diamination 87
References 89
3.2 Oxidative Allylic Oxygénation and Amination 92
Sabine Laschat, Volker Rabe, and Angelika Baro
3.2.1 Introduction 92
3.2.2 Iron-catalyzed Allylic Oxidations 93
3.2.2.1 Simple Iron Salts 93
3.2.2.2 Fe(III) Complexes with Bidentate Iigands 94
3.2.2.3 Fe3+/Fe2+ Porphyrin and Phthalocyanine Complexes 95
3.2.2.4 Iron(III) Salen Complexes 100
3.2.2.5 Non-heme Iron Complexes with Terra- and Pentadentate
Iigands 100
3.2.3 Oxidative Allylic Animations 103
3.2.4 Conclusion 107
References 107
3.3 Oxidation of Heteroatoms (N and S) 109
Olga García Manchem and Carsten Bolm
3.3.1 Oxidation of Nitrogen Compounds 109
3.3.1.1 Oxidation of Hydroxylamines to Nitroso Compounds 109
3.3.1.2 Oxidation of Arylamines 110
3.3.1.3 Other N-Oxidations 110
3.3.2 Oxidation of Sulfur Compounds 111
3.3.2.1 Oxidation of Thiols to Disulfides 111
3.3.2.2 Oxidation of Sulfides 113
3.3.2.3 Oxidative Imination of Sulfur Compounds 119
References 122
4 Reduction of Unsaturated Compounds with Homogeneous
Iron Catalysts 125
Stephan Enthaler, Kathrin Junge, and Matthias Belter
4.1 Introduction 125
4.2 Hydrogénation of Carbonyl Compounds 125
4.3 Hydrogénation of Carbon-Carbon Double Bonds 129
4.4 Hydrogénation of Imines and Similar Compounds 136
4.5 Catalytic Hydrosilylations 136
4.6 Conclusion 141
References 142
5 Iron-catalyzed Cross-coupling Reactions 147
Andreas Leaner
5.1 Introduction 147
5.2 Cross-coupling Reactions of Alkenyl Electrophiles 147
5.3 Cross-coupling Reactions of Aryl Electrophiles 154
5.4 Cross-coupling Reactions of Alkyl Electrophiles 161
5.5 Cross-coupling Reactions of Acyl Electrophiles 168
5.6 Iron-catalyzed Carbometallation Reactions 170
5.7 Conclusion 172
References 173
6 Iron-catalyzed Aromatic Substitutions 177
Jette Kischel, Kristin Mertins, Irina Jovel, Alexander Zapf, and Matthias Beller
6.1 General Aspects 177
6.2 Electrophilic Aromatic Substitutions 178
6.2.1 Halogenation Reactions 178
6.2.2 Nitration Reactions 179
6.2.3 Sulfonylation Reactions 180
6.2.4 Friedel-Crafts Acylations 181
6.2.5 Friedel-Crafts Alkylations 183
6.2.5.1 Alkylation with Alcohols, Ethers and Esters 184
6.2.5.2 Alkylation with Alkenes 186
6.3 Nudeophilic Aromatic Substitutions 188
References 191
7 Iron-catalyzed Substitution Reactions 197
Bernd Plietker
7.1 Introduction 197
7.2 Iron-catalyzed Nudeophilic Substitutions 297
7.2.1 Nudeophilic Substitutions of Non-activated C-X Bonds 197
7.2.1.1 Introduction 197
7.2.1.2 Nudeophilic Substitutions Using Lewis Acidic Fe Catalysts 198
7.2.1.3 Substitutions Catalyzed by Ferrate Complexes 199
7.2.2 Nudeophilic Substitution of Allylic and Propargylic C-X Bonds 202
7.2.2.1 Reactions Catalyzed by Lewis Acidic Fe Salts 202
7.2.2.2 Nudeophilic Substitutions Involving Ferrates 205
7.3 Condusion 213
References 234
8 Addition and Conjugate Addition Reactions to Carbonyl
Compounds 217
Jens Christoffers, Herbert Frey, and Anna Rosiak
8.1 Introduction 217
8.2 Additions to Aldehydes and Ketones 218
8.2.1 Oxygen Nudeophiles 218
8.2.2 Carbon Nudeophiles 219
8.3 Additions to Imines and Iminium Ions 223
8.4 Additions to Carboxylic Acids and Their Derivatives 224
8.4.1 Oxygen Nudeophiles 224
8.4.2 Carbon Nudeophiles 225
8.5 Conjugate Addition to oc,ß-Unsaturated Carbonyl
Compounds 226
8.5.1 Carbon Nudeophiles 226
8.5.1.1 Michael Reactions 226
8.5.1.2 Vinylogous Michael Reactions 230
8.5.1.3 Asymmetric Michael Reactions 232
8.5.1.4 Michael Reactions in Ionic Liquids and Heterogeneous
Catalysis 233
8.5.2 Nitrogen Nudeophiles 235
8.6 Synthesis of Heterocycles 236
8.6.1 Pyridine and Quinoline Derivatives 236
8.6.2 Pyrimidine and Pyrazine Derivatives 238
8.6.3 Benzo- and Dibenzopyrans 238
References 239
9 Iron-catalyzed Cycloadditions and Ring Expansion Reactions 245
Gerhard Hilt and Judith Janikowski
9.1 Introduction 245
9.2 Cydoisomerization and Alder-Ene Reaction 245
9.3 [2+l]-Cydoadditions 249
9.3.1 Iron-catalyzed Aziridine Formation 249
9.3.2 Iron-catalyzed Epoxide Formation 251
9.3.3 Iron-catalyzed Cyclopropane Formation 252
9.4 [2+2]-Cydoaddition 254
9.5 [4+l]-Cydoadditions 256
9.6 [4+2]-Cydoadditions 257
9.6.1 Diels-Alder Reactions with Normal Electron Demand 257
9.6.2 Diels-Alder Reactions with Neutral Electron Demand 259
9.6.3 Diels-Alder Reactions with Inverse Electron Demand 260
9.7 Cydotrimerization 260
9.8 [3+2]-Cydoadditions 262
9.9 [3+3]-Cydoadditions 263
9.10 Ring Expansion Reactions 263
9.11 Condusion 266
References 266
Index 271 |
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id | DE-604.BV023406667 |
illustrated | Illustrated |
index_date | 2024-07-02T21:25:50Z |
indexdate | 2024-07-20T09:45:29Z |
institution | BVB |
isbn | 9783527319275 3527319271 |
language | English |
oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-016589346 |
oclc_num | 248628844 |
open_access_boolean | |
owner | DE-91G DE-BY-TUM DE-703 DE-19 DE-BY-UBM DE-83 DE-11 |
owner_facet | DE-91G DE-BY-TUM DE-703 DE-19 DE-BY-UBM DE-83 DE-11 |
physical | XV, 279 S. graph. Darst. |
publishDate | 2008 |
publishDateSearch | 2008 |
publishDateSort | 2008 |
publisher | WILEY-VCH |
record_format | marc |
spelling | Iron catalysis in organic chemistry reactions and applications ed. by Bernd Plietker Weinheim WILEY-VCH 2008 XV, 279 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Organische Synthese (DE-588)4075695-6 gnd rswk-swf Eisenkomplexe (DE-588)4222910-8 gnd rswk-swf Katalysator (DE-588)4029919-3 gnd rswk-swf Eisenkomplexe (DE-588)4222910-8 s Katalysator (DE-588)4029919-3 s Organische Synthese (DE-588)4075695-6 s DE-604 Plietker, Bernd 1971- Sonstige (DE-588)12175880X oth text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3060782&prov=M&dok_var=1&dok_ext=htm Inhaltstext HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016589346&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
spellingShingle | Iron catalysis in organic chemistry reactions and applications Organische Synthese (DE-588)4075695-6 gnd Eisenkomplexe (DE-588)4222910-8 gnd Katalysator (DE-588)4029919-3 gnd |
subject_GND | (DE-588)4075695-6 (DE-588)4222910-8 (DE-588)4029919-3 |
title | Iron catalysis in organic chemistry reactions and applications |
title_auth | Iron catalysis in organic chemistry reactions and applications |
title_exact_search | Iron catalysis in organic chemistry reactions and applications |
title_exact_search_txtP | Iron catalysis in organic chemistry reactions and applications |
title_full | Iron catalysis in organic chemistry reactions and applications ed. by Bernd Plietker |
title_fullStr | Iron catalysis in organic chemistry reactions and applications ed. by Bernd Plietker |
title_full_unstemmed | Iron catalysis in organic chemistry reactions and applications ed. by Bernd Plietker |
title_short | Iron catalysis in organic chemistry |
title_sort | iron catalysis in organic chemistry reactions and applications |
title_sub | reactions and applications |
topic | Organische Synthese (DE-588)4075695-6 gnd Eisenkomplexe (DE-588)4222910-8 gnd Katalysator (DE-588)4029919-3 gnd |
topic_facet | Organische Synthese Eisenkomplexe Katalysator |
url | http://deposit.dnb.de/cgi-bin/dokserv?id=3060782&prov=M&dok_var=1&dok_ext=htm http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016589346&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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