Cleavage of carbon-carbon single bonds by transition metals
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[2016]
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| 245 | 1 | 0 | |a Cleavage of carbon-carbon single bonds by transition metals |c edited by Masahiro Murakami and Naoto Chatani |
| 264 | 1 | |a Weinheim |b Wiley-VCH Verlag GmbH & Co. KGaA |c [2016] | |
| 264 | 4 | |c © 2016 | |
| 300 | |a XII, 278 Seiten |b Illustrationen | ||
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| 653 | |a Catalysis | ||
| 653 | |a Chemie | ||
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| 653 | |a Industrial Chemistry | ||
| 653 | |a Katalyse | ||
| 653 | |a Metallorganische Verbindungen | ||
| 653 | |a Organometallchemie | ||
| 653 | |a Organometallic Chemistry | ||
| 653 | |a Technische u. Industrielle Chemie | ||
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Datensatz im Suchindex
| _version_ | 1819766517816885248 |
|---|---|
| adam_text | CONTENTS
PREFACE IX
LIST OF CONTRIBUTORS XI
I FUNDAMENTAL REACTIONS TO CLEAVE CARBON -CARBON O-BONDS WITH
TRANSITION METAL COMPLEXES 1
MASAHIRO MURAKAMI
AND NAOKI ISHIDA
1.1 INTRODUCTION 1
1.2 OXIDATIVE ADDITION 1
1.2.1 OXIDATIVE ADDITION UTILIZING RING STRAIN 3
1.2.2 CHELATION-ASSISTED OXIDATIVE ADDITION 5
1.2.3 OXIDATIVE ADDITION DRIVEN BY AROMATIZATION 6
1.2.4 OXIDATIVE ADDITION OF KETONES 7
1.2.5 OXIDATIVE ADDITION OF NITRILES 11
1.2.6 OTHERS 13
1.3 P-CARBON ELIMINATION 14
1.3.1 P-CARBON ELIMINATION OF LATE TRANSITION METAL ALKYLS IS
1.3.2 P-CARBON ELIMINATION FROM EARLY TRANSITION METAL ALKYLS 16
1.3.3 P-CARBON ELIMINATION OF LATE TRANSITION METAL ALCOHOLATES 17
1.4 RETROALLYLATION 20
1.5 MIGRATORY DEINSERTION OF A CARBONYL GROUP 22
1.6 DECARBOXYLATION 24
1.7 RETRO-OXIDATIVE CYCLIZATION 25
1.8 1,2-MIGRATION 27
1.9 CLEAVAGE OF C-C MULTIPLE BONDS 29
1.10 SUMMARY 30
REFERENCES 30
2 REACTIONS OFTHREE-MEMBERED RING COMPOUNDS 35
TAKANORI MATSUDA
2.1 INTRODUCTION 35
2.2 CYCLOPROPANES 35
2.3 BICYCLO[
1.1.0]
BUTANES 40
2.4 BICYCLO[2.1.0]PENTANES 43
HTTP://D-NB.INFO/1070857084
VII
CONTENTS
2.5 QUADRICYCLANES AND RELATED COMPOUNDS 45
2.6 SPIROPENTANES 47
2.7 CYCLOPROPANOLS 48
2.8 VINYLCYCLOPROPANES 51
2.9 METHYLENECYCLOPROPANES 59
2.10 ALKYNYLCYCLOPROPANES 70
2.11 CYCLOPROPYL KETONES AND IMINES 71
2.12 CYCLOPROPENES 73
2.13 BENZOCYCLOPROPENES 78
2.14 CYCLOPROPENONES 80
2.15 CONCLUSION 82
REFERENCES 83
3 REACTIONS OF FOUR-MEMBERED RING COMPOUNDS 89
TAKANORI MATSUDA
3.1 INTRODUCTION 89
3.2 CUBANE DERIVATIVES 89
3.3 BIPHENYLENES 90
3.4 VINYLCYCLOBUTANE AND METHYLENECYCLOBUTANE DERIVATIVES 93
3.5 CYCLOBUTANOL AND CYCLOBUTANO NE DERIVATIVES 95
3.5.1 REACTIONS INVOLVING P-CARBON ELIMINATION OF TRANSITION METAL
CYCLOBUTANOLATES 95
3.5.2 REACTIONS INVOLVING FORMATION OF FIVE-MEMBERED
METALLACYCLES 108
3.6 CYCLOBUTENONES AND CYCLOBUTENEDIONES 112
3.7 CONCLUSION 115
REFERENCES 115
4 REACTIONS INVOLVING ELIMINATION OF C0
2
AND KETONES 119
TETSUYA SATOH
AND MASAHIRO MIURA
4.1 INTRODUCTION 119
4.2 REACTIONS OF BENZOIC ACIDS 119
4.2.1 ARYLATION 119
4.2.2 ALKENYLATION 127
4.2.3 ANNULATION 130
4.2.4 MISCELLANEOUS REACTIONS 132
4.3 REACTIONS OF HETEROARENECARBOXYLIC ACIDS 134
4.4 REACTIONS OF ACRYLIC ACIDS 139
4.5 REACTIONS OF PROPIOLIC ACIDS 142
4.6 REACTIONS OF A-KETO CARBOXYLIC ACIDS 144
4.7 REACTIONS OF ALKANOIC ACIDS 148
4.8 REACTIONS OF TERTIARY ALCOHOLS 151
4.8.1 ARYLATION 151
4.8.2 ALKENYLATION, ANNULATION, AND ALKYLATION I55
CONTENTS VII
4.9 SUMMARY AND CONCLUSIONS 159
REFERENCES 160
5 RETRO-ALLYLATION AND DEALLYLATION 165
HIDEKI
YORIMITSU
5.1 INTRODUCTION 165
5.2 RETRO-ALLYLATION 165
5.2.1 RUTHENIUM CATALYSIS: THE PIONEER 167
5.2.2 PALLADIUM CATALYSIS: REGIO- AND STEREOSELECTIVE ALLYLATION OF ARYL
HALIDES 168
5.2.2.1 ADVANTAGE OF PALLADIUM-CATALYZED ALLYLATION VIA
RETRO-ALLYLATION 168
5.2.2.2 PALLADIUM-CATALYZED REGIO- AND STEREOSELECTIVE ALLYLATION VIA
RETRO-ALLYLATION 170
5.2.2.3 VARIANTS OF PALLADIUM-CATALYZED RETRO-ALLYLATION 176
5.2.3 NICKEL CATALYSIS 179
5.2.4 RHODIUM CATALYSIS 181
5.2.5 COPPER CATALYSIS 184
5.3 DEALLYLATION 185
5.3.1 OXIDATIVE ADDITION OF ALLYLIC COMPOUNDS 185
5.3.2 METALATION-P-CARBON ELIMINATION SEQUENCE 187
5.4 SUMMARY AND CONCLUSIONS 189
REFERENCES 190
6 REACTIONS VIA CLEAVAGE OF CARBON-CARBON BONDS OF KETONES AND
NITRILES 193
MAMORU TOBISU
6.1 INTRODUCTION 193
6.2 CATALYTIC REACTIONS OF KETONES VIA C-C BOND CLEAVAGE 194
6.2.1 REACTIONS OF KETONES WITHOUT CHELATION ASSISTANCE 194
6.2.2 REACTIONS OF KETONES CONTAINING A DIRECTING GROUP 196
6.2.3 REACTIONS OF KETONES USING A TEMPORARY DIRECTING GROUP 200
6.2.4 C-C BOND CLEAVAGE OF KETONES VIA PATHWAYS OTHER THAN OXIDATIVE
ADDITION 202
6.2.4.1 C-C BOND CLEAVAGE OF 1,3-DICARBONYL COMPOUNDS 202
6.2.4.2 C-C BOND CLEAVAGE OF KETONES OTHER THAN 1,3-DICARBONYL
COMPOUNDS 203
6.3 CATALYTIC REACTIONS OF NITRILES VIA C-C BOND CLEAVAGE 205
6.3.1 C-CN BOND CLEAVAGE VIA OXIDATIVE ADDITION 205
6.3.2 C-CN BOND CLEAVAGE VIA SILYLMETALATION/ISOCYANIDE EXTRUSION
SEQUENCE 212
6.3.3 C-CN BOND CLEAVAGE VIA OTHER MECHANISMS 215
6.4 SUMMARY AND OUTLOOK 216
REFERENCES 217
VIII
| CONTENTS
7 MISCELLANEOUS 221
MASAHIRO MURAKAMI
AND NAOKI ISHIDA
7.1 INTRODUCTION 221
7.2 CLEAVAGE OF C-C SINGLE BONDS 221
7.3 CLEAVAGE OF C=C DOUBLE BONDS 235
7.4 CLEAVAGE OF C-C BONDS OF AROMATICS 237
7.5 CLEAVAGE OF C=C TRIPLE BONDS 242
7.6 SUMMARY 248
REFERENCES 248
8 TOTAL SYNTHESES OF NATURAL PRODUCTS AND BIOLOGICALLY ACTIVE
COMPOUNDS BY TRANSITION-METAL-CATALYZED C-C CLEAVAGE 253
MASAHIRO MURAKAMI
AND NAOKI ISHIDA
8.1 INTRODUCTION 253
8.2 SYNTHESIS OF ()-NANAOMYCIN A THROUGH ALKYNE INSERTION INTO A
C - C BOND OF BENZOCYCLOBUTENEDIONE 253
8.3 ENANTIOSELECTIVE SYNTHESIS OF (-)-PSEUDOLARIC ACID B VIA AN
INTRAMOLECULAR [5+2] CYCLOADDITION REACTION OF A VINYLCYCLOPROPANE
WITH AN ALKYNE
254
8.4 ENANTIOSELECTIVE SYNTHESIS OF (-)-ESERMETHOLE VIA ASYMMETRIC
ALKENE INSERTION INTO A C-C BOND OF ARYL CYANIDES 256
8.5 ENANTIOSELECTIVE SYNTHESIS OF BENZOBICYCLO[2.2.2]OCTENONES VIA
ASYMMETRIC ALKENE INSERTION INTO A C-C BOND OF
CYCLOBUTANONES 257
8.6 SYNTHESIS OF THE PROPOSED STRUCTURE OF CYCLOINUMAKIOL THROUGH
SITE-SELECTIVE INSERTION OF ALKENES INTO A C-C BOND OF
BENZOCYCLOBUTENONES 259
8.7 ENANTIOSELECTIVE SYNTHESIS OF (*)-(/?)-HERBERTENOL THROUGH
ASYMMETRIC C-C CLEAVAGE 260
8.8 ENANTIOSELECTIVE SYNTHESIS OF (+)-LAURENE VIA RING-EXPANSION OF
1-VINYLCYCLOBUTANOL 261
8.9 SYNTHESIS OF ()-CUPARENONE THROUGH SKELETAL REORGANIZATION OF
SPIROPENTANES 262
8.10 TOTAL SYNTHESIS OF (*)-CYANTHIWIGIN F BY DECARBOXYLATIVE
ASYMMETRIC ALLYLATION 264
8.11 TOTAL SYNTHESES VIA HYDROGENOLYSIS OF CYCLOPROPANES 265
8.12 TOTAL SYNTHESES VIA DECARBONYLATION 266
8.13 SUMMARY AND CONCLUSIONS 269
REFERENCES 270
INDEX 273
|
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| genre_facet | Aufsatzsammlung |
| id | DE-604.BV043175884 |
| illustrated | Illustrated |
| indexdate | 2024-12-24T04:44:09Z |
| institution | BVB |
| isbn | 9783527336326 9783527680092 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-028599966 |
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| publishDateSearch | 2016 |
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| publisher | Wiley-VCH Verlag GmbH & Co. KGaA |
| record_format | marc |
| spellingShingle | Cleavage of carbon-carbon single bonds by transition metals Spaltungsreaktion (DE-588)4322389-8 gnd Kohlenstoff-Kohlenstoff-Bindung (DE-588)4164549-2 gnd Übergangsmetallkomplexe (DE-588)4131837-7 gnd |
| subject_GND | (DE-588)4322389-8 (DE-588)4164549-2 (DE-588)4131837-7 (DE-588)4143413-4 |
| title | Cleavage of carbon-carbon single bonds by transition metals |
| title_auth | Cleavage of carbon-carbon single bonds by transition metals |
| title_exact_search | Cleavage of carbon-carbon single bonds by transition metals |
| title_full | Cleavage of carbon-carbon single bonds by transition metals edited by Masahiro Murakami and Naoto Chatani |
| title_fullStr | Cleavage of carbon-carbon single bonds by transition metals edited by Masahiro Murakami and Naoto Chatani |
| title_full_unstemmed | Cleavage of carbon-carbon single bonds by transition metals edited by Masahiro Murakami and Naoto Chatani |
| title_short | Cleavage of carbon-carbon single bonds by transition metals |
| title_sort | cleavage of carbon carbon single bonds by transition metals |
| topic | Spaltungsreaktion (DE-588)4322389-8 gnd Kohlenstoff-Kohlenstoff-Bindung (DE-588)4164549-2 gnd Übergangsmetallkomplexe (DE-588)4131837-7 gnd |
| topic_facet | Spaltungsreaktion Kohlenstoff-Kohlenstoff-Bindung Übergangsmetallkomplexe Aufsatzsammlung |
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