Modern organonickel chemistry:
Gespeichert in:
| Format: | Buch |
|---|---|
| Sprache: | English |
| Veröffentlicht: |
Weinheim
WILEY-VCH
2005
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XIX, 327 S. graph. Darst. 240 mm x 170 mm |
| ISBN: | 3527307966 9783527307968 |
Internformat
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| 245 | 1 | 0 | |a Modern organonickel chemistry |c ed. by Yoshinao Tamaru |
| 264 | 1 | |a Weinheim |b WILEY-VCH |c 2005 | |
| 300 | |a XIX, 327 S. |b graph. Darst. |c 240 mm x 170 mm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
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| 650 | 4 | |a Nickelorganische Verbindungen | |
| 650 | 4 | |a Organonickel compounds | |
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| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Tamaru, Yoshinao |e Sonstige |4 oth | |
| 856 | 4 | 2 | |m HBZ Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=013009637&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
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Datensatz im Suchindex
| _version_ | 1804133122053242880 |
|---|---|
| adam_text | V
Contents
Preface xi
List of Contributors xv
Abbreviations xvii
1 Introductory Guide to Organonickel Chemistry 1
Yoshinao Tamaru
1.1 The Crystal Field 2
1.2 Nickel has Wings: The Mond Method 3
1.3 The Ligand Field 3
1.4 The Formal Oxidation Number 6
1.5 The 16- and 18-Electron Rule 8
1.6 The Structure, Reactivity, and Electronic Configuration of Nickel-
Complexes 11
1.7 The Elementary Reactions 15
1.7.1 Oxidative Addition 15
1.7.2 Insertion 18
1.7.3 Transmetallation 20
1.7.4 Reductive Elimination 23
1.7.5 /^-Hydrogen Elimination 26
1.7.6 a- and /?-Carbon Elimination (C-C Bond Cleavage) 28
1.8 Catalytic Reactions 29
References 37
2 Nickel-catalyzed Cross-coupling Reactions 41
Tamotsu Takahashi and Ken-Ichiro Kanno
2.1 Cross-coupling of Alkyl Electrophiles with Organometallic
Compounds 41
2.2 Cross-coupling of Alkenyl Electrophiles with Organometallic
Compounds 45
2.3 Cross-coupling of Allyl Electrophiles with Organometallic
Compounds 47
Modem Organonickel Chemistry. Edited by Y. Tamaru
Copyright © 2005 WILEY-VCH Verlag GmbH Co. KGaA, Weinheim
ISBN: 3-527-30796-6
vi Contents
2.4 Cross-coupling of Aryl Electrophiles with Organometallic
Compounds 48
2.5 Asymmetric Cross-coupling Reactions 53
References 53
3 Reaction of Alkenes and Ally I Alcohol Derivatives 56
Yuichi Kobayashi
3.1 Hydrovinylation of Olefins 56
3.2 Hydrocyanation of Olefins 59
3.3 Heck-type Cydization 60
3.4 Olefin Insertion 61
3.5 Nickel-catalyzed Hydrozincation of Olefins 64
3.6 Ni-catalyzed Addition of Organometallics to Electron-deficient
Olefins 65
3.6.1 The Reaction with Organometallics 65
3.6.2 The Reaction with Organic Halides as Nudeophiles 68
3.7 Polymerization of Ethylene and a-Olefins using Ni(II)-based
Catalysts 70
3.8 The Nudeophilic Reactions of n-Allylnickel Complexes 72
3.9 w-Allylnickel Complexes from Enones 74
3.10 Carbonylative Cycloaddition of Allylic Halides and Acetylenes 75
3.11 Nudeophilic Allylation Toward re-Allylnickel Complexes 77
3.11.1 Allylation with Gngnard Reagents 77
3.11.2 Allylation with Soft Nudeophiles 80
3.11.3 Regiochemical Control Based on Internal Chelation 80
3.11.4 Organometallics other than Grignard Reagents for Allylation 82
3.11.4.1 Ni-catalyzed Allylation with Lithium Borates Derived from Trimethyl
Borate 82
3.11.4.2 Allylation with Lithium Borates Derived from Acetylene 84
3.11.4.3 Allylation with Borates Derived from Cyclic Boronate Esters 85
3.11.5 The Design of Functionalized Reagents for Allylation 85
3.11.6 Nickel-catalyzed Reactions of Cyclopentenyl Acetate and Borates 87
3.11.7 Synthetic Application of Nickel-catalyzed Reactions of Cyclopentenyl
Acetate and Borates 89
3.11.8 Extension of the Lithium Borate/Nickel Catalyst for Coupling with
Alkenyl and Aryl Substrates 91
3.12 Nickel Enolates 92
3.12.1 Reactions of Ni(II) Complexes with Lithium or Potassium
Enolates 93
3.12.2 The Reformatsky-type Reaction 95
3.12.3 Other Reactions through Nickel Enolates 96
References 97
4 Reaction of Alkynes 102
Shin-ichi Ikeda
4.1 Hydrogenation 103
Contents vii
4.2 Hydrometallation and Related Reactions 104
4.2.1 Hydrosilylation and Hydrostannylation 104
4.2.2 Hydroboration 106
4.2.3 Hydroalummation 107
4.2.4 Miscellaneous: the Addition of H-P and H-S Groups 107
4.3 bis-Metallation 107
4.3.1 bis-Silylation and bis-Germylation 108
4.3.2 Silaboration and Geraboration 110
4.4 Hydrocyanation, Hydroacylation, and Related Reactions 111
4.5 Carbometallation and Related Reactions 113
4.5.1 Carbomagnesiation 113
4.5.2 Carbozmcation 114
4.5.3 Carbostannylation 135
4.5.4 Miscellaneous 137
4.6 The Sequential Reaction 138
4.6.1 Sequential Reaction Starting with Activation of Organic Halides 3 38
4.6.2 Sequential Reaction with Enones 123
4.6.3 Sequential Reaction with Aldehydes and Imines 127
4.6.4 Sequential Reaction with Epoxides 129
4.7 Addenda 131
References 132
5 Reaction of Dienes and Allenes 137
Masanari Kimura and Yoshinao Tamaru
5.1 Dimerization and Polymerization of 1,3-Dienes 137
5.1.1 Structure of Ni-(butadiene)2 Complexes Stabilized by Phosphine
Ligands 138
5.1.2 Dimerization of Substituted 1,3-Dienes 139
5.1.3 Ni-catalyzed Polymerization of Butadiene 141
5.1.4 Stereo- and Regioselective Polymerization of Conjugated Cyclic
Dienes 143
5.2 Allylation and Homoallylation of Aldehydes with Dienes and
Allenes 143
5.2.1 Allylation of Aldehydes via Dimerization of 1,3-Dienes 143
5.2.2 Allylation of Aldehydes with Dienes Promoted by Silane
(R4-nSiHn) 145
5.2.3 Allylation of Aldehydes with Dienes Promoted by Diisobutylaluminum
Hydride (DIBAL) or Diisobutylaluminum(III)(acac) 147
5.2.4 Homoallylation of Aldehydes Promoted by Triethylborane or
Diethylzinc 353
5.2.5 Allylation of Aldehydes Promoted by Dimethylzinc, Tnmethyborane, and
Related Compounds: the Three-component Connection Reactions 354
5.2.6 The Multi-component Connection Reaction 157
5.2.7 Cydization of Allenyl Aldehydes 158
5.3 Addition Reaction of HX on Dienes and Allenes 360
5.3.1 Addition of Active Methylene Compounds to 1,3-Dienes 360
viii Contents
5.3.2 Hydrocyanation of 1,3-Dienes 160
5.3.3 Hydroamination of 1,3-Dienes and Allenes 363
5.3.4 1,4-Dialkenylation of 1,3-Dienes 162
5.3.5 Addition of Si-B and Csp2-B Compounds on 1,3-Dienes 363
5.3.6 Carbostannylation of 1,3-Dienes and Allenes 164
5.3.7 Carbozirconation of Allenes 366
5.3.8 Wurtz-type Coupling Reaction of Organic Halides and Grignard
Reagents Mediated by the Butadiene-Nickel Complex (5.1) 367
5.3.9 Carbosilylation of Diene Dimers 168
References 168
6 Cyclooligomerization and Cycloisomerization of Alkenes and Allcynes 171
Shinichi Saito
6.1 Cyclooligomerization of Alkenes 171
6.2 Cycloisomerization of Alkenes 174
6.3 Cyclooligomenzation of Alkynes 175
6.3.1 Cydotrimerization of Alkynes 175
6.3.2 Co-cyclotrimerization and Cycloisomerization of Alkynes 178
6.3.3 Co-cyclotnmenzation of Alkynes with other Unsaturated
Compounds 180
6.3.4 Cydotetramerization of Alkynes 183
6.3.5 Co-cyclotetramerrzation of Alkynes 385
6.4 Cydooligomerization of Dienes 385
6.4.1 Cydodimenzation and Cydotrimerization of 1,3-Butadiene 386
6.4.2 Cyclodimerization and Cydotrimerization of Substituted
1,3-Dienes 188
6.4.3 Co-cyclooligomenzation of 1,3-Dienes 189
6.4.4 Co-cycloisomerization of 1,3-Dienes 191
6.5 Cydooligomerization of Allenes and Cumulenes 392
6.5.1 Cydooligomerization of Allene (1,2-Propadiene) 192
6.5.2 Cyclooligomerization of Substituted Allenes 394
6.5.3 Cyclooligomerization of Cumulenes 395
6.6 Cydooligomerization and Cycloisomerization of Miscellaneous
Compounds 397
References 398
7 Nickel-mediated and -catalyzed Carboxylation 205
Miwako Mori and Masanori Takimoto
7.1 Nickel-mediated or-catalyzed Carboxylation of 1,3-Diene 205
7.2 Nickel-mediated or-catalyzed Carboxylation of Alkyne 231
7.3 Nickel-mediated Carboxylation of Alkene 235
7.4 Nickel-mediated Carboxylation of Allene 218
7.5 Various Nickel-mediated Carboxylations 220
7.6 Perspectives 222
References 222
Contents ix
8 Carbonylation and Decarbonylation 224
Yoshmao Tamaru
8.1 Decarbonylation 224
8.2 Electrochemical Carbonylation 227
8.2.1 Method A: Utilization of CO 228
8.2.2 Method B: Utilization of CO2 as a CO Source 228
8.2.3 Method C: Utilization of Fe(CO)5 as a CO Source 228
8.3 Termination of Cascade Reactions by Carbonylation 229
8.4 Carbonylation Forming Carboxylic Acid under Phase-Transfer
Conditions 231
References 238
9 Asymmetric Synthesis 240
Ryo Shintani and Tamio Hayashi
9.1 The Cross-coupling Reaction 240
9.2 Allyhc Substitution 246
9.2.1 Allylic Substitution by Carbon Nucleophiles 246
9.2.2 Allylic Substitution by Hydnde Nucleophiles 249
9.3 Hydrocyanation and Hydrovinylation Reactions 250
9.4 Reactions of Organometallic Reagents with Aldehydes and Enones 255
9.4.1 Reaction with Aldehydes 255
9.4.2 Reaction with Enones 256
9.5 Activation of Carbonyl Compounds for Cycloaddition and Other Related
Reactions 260
9.5.1 The Diels-Alder Reaction 260
9.5.2 The 1,3-Dipolar Cycloaddition Reaction 262
9.5.3 The Ene Reaction and Conjugate Addition Reaction 263
9.5.4 Addition of Nickel-Enolate Intermediates 267
9.6 Other Reactions 269
References 269
10 Heterogeneous Catalysis 273
Tsutomu Osawa
10.1 Heterogeneous Catalysts and Catalytic Reactions 273
10.1.1 Comparison of Heterogeneous and Homogeneous Catalysts and
Catalytic Reactions 274
10.1.2 Reactions over Heterogeneous Catalysts in Liquids 275
10.2 Heterogeneous Ni Catalysts 276
10.2.1 Reactions in the Petroleum Industry 276
10.2.2 Transformation of Organic Functional Groups 278
10.2.2.1 Raney Nickel 280
10.2.2.2 Nickel Boride 282
10.2.2.3 Supported Nickel Catalysts 283
10.3 Asymmetric Syntheses over Heterogeneous Nickel Catalysts 285
10.3.1 Diastereo-differentiating Reactions 285
x Contents
10.3.2 Enantio-differentiating Reactions 286
10.4 Tartaric Acid-modified Nickel Catalyst 287
10.4.1 Preparation of the Base Ni Catalyst 288
10.4.1.1 Raney Ni Catalyst 289
10.4.1.2 Reduced Ni Catalyst 289
10.4.1.3 Supported Ni Catalyst 290
10.4.1.4 Fine Nickel Powder 290
10.4.2 Modification of the Base Nickel Catalyst 291
10.4.3 Enantio-differentiating Hydrogenation over Tartaric Acid-NaBr-modified
Nickel Catalysts 291
10.4.3.1 Hydrogenation of Functionalized Ketone 292
10.4.3.2 Hydrogenation of Alkyl Ketones 294
10.4.4 What Happens on the Nickel Surface? 296
10.4.4.1 Adsorption of a Modifier and a Co-modifier 296
10.4.4.2 Mechanism of Enantio-differentiating Hydrogenation 298
10.4.5 Concluding Remarks on Tartaric Acid-NaBr-modified Ni Catalysts 302
References 302
Index 306
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| id | DE-604.BV019681670 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T20:03:41Z |
| institution | BVB |
| isbn | 3527307966 9783527307968 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-013009637 |
| oclc_num | 249465674 |
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| owner_facet | DE-91G DE-BY-TUM DE-703 DE-19 DE-BY-UBM DE-29T DE-11 |
| physical | XIX, 327 S. graph. Darst. 240 mm x 170 mm |
| publishDate | 2005 |
| publishDateSearch | 2005 |
| publishDateSort | 2005 |
| publisher | WILEY-VCH |
| record_format | marc |
| spelling | Modern organonickel chemistry ed. by Yoshinao Tamaru Weinheim WILEY-VCH 2005 XIX, 327 S. graph. Darst. 240 mm x 170 mm txt rdacontent n rdamedia nc rdacarrier Nickelorganische Verbindungen Organonickel compounds Nickelorganische Verbindungen (DE-588)4171817-3 gnd rswk-swf Nickelorganische Verbindungen (DE-588)4171817-3 s DE-604 Tamaru, Yoshinao Sonstige oth HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=013009637&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Modern organonickel chemistry Nickelorganische Verbindungen Organonickel compounds Nickelorganische Verbindungen (DE-588)4171817-3 gnd |
| subject_GND | (DE-588)4171817-3 |
| title | Modern organonickel chemistry |
| title_auth | Modern organonickel chemistry |
| title_exact_search | Modern organonickel chemistry |
| title_full | Modern organonickel chemistry ed. by Yoshinao Tamaru |
| title_fullStr | Modern organonickel chemistry ed. by Yoshinao Tamaru |
| title_full_unstemmed | Modern organonickel chemistry ed. by Yoshinao Tamaru |
| title_short | Modern organonickel chemistry |
| title_sort | modern organonickel chemistry |
| topic | Nickelorganische Verbindungen Organonickel compounds Nickelorganische Verbindungen (DE-588)4171817-3 gnd |
| topic_facet | Nickelorganische Verbindungen Organonickel compounds |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=013009637&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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