Catalytic hydroarylation of carbon-carbon multiple bonds:
Gespeichert in:
| Weitere Verfasser: | , , |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Weinheim, Germany
Wiley-VCH
[2018]
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| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | ix, 403 Seiten Illustrationen |
| ISBN: | 9783527340132 3527340130 |
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| 245 | 1 | 0 | |a Catalytic hydroarylation of carbon-carbon multiple bonds |c edited by Lutz Ackermann, T. Brent Gunnoe, Laurel Goj Habgood |
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| 264 | 4 | |c © 2018 | |
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| 653 | |a Catalysis | ||
| 653 | |a Chemie | ||
| 653 | |a Chemistry | ||
| 653 | |a Hydroarylierung | ||
| 653 | |a Industrial Chemistry | ||
| 653 | |a Katalyse | ||
| 653 | |a Nanomaterialien | ||
| 653 | |a Nanomaterials | ||
| 653 | |a Nanotechnologie | ||
| 653 | |a Nanotechnology | ||
| 653 | |a Pharmaceutical & Medicinal Chemistry | ||
| 653 | |a Pharmazeutische u. Medizinische Chemie | ||
| 653 | |a Polymer Science & Technology | ||
| 653 | |a Polymer Synthesis | ||
| 653 | |a Polymersynthese | ||
| 653 | |a Polymerwissenschaft u. -technologie | ||
| 653 | |a Technische u. Industrielle Chemie | ||
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Datensatz im Suchindex
| _version_ | 1804178125481836544 |
|---|---|
| adam_text | CONTENTS
INTRODUCTION AND PREFACE
1
LAUREL
G. HABGOOD, LUTZ ACKERMANN, AND T. BRENT GUNNOE
REFERENCES 3
1 FUNCTIONALIZATION OF HETEROAROMATIC SUBSTRATES USING GROUPS 9
AND 10 CATALYSTS
5
PEDRO VILLUENDAS, SARA RUIZ; AND ESTEBAN P. URRIOLABEITIA
1.1 INTRODUCTION 5
1.2 THIOPHENES, FURANS, AND RELATED HETEROCYCLES
8
1.3 PYRROLES, INDOLES, PYRIDINES, AND IMIDAZOPYRIDINES 21
1.4 AZOLES AND OTHER MISCELLANEOUS HETEROCYCLES 31
1.5 SUMMARY 39
REFERENCES 40
2
RUTHENIUM CATALYSTS FOR THE ALKYLATION OF FUNCTIONALIZED
ARENES AND HETEROAROMATIC SUBSTRATES VIA HYDROARYLATION
49
DAVID J. BURNS, SERGEI I. KOZHUSHKOV, AND LUTZ ACKERMANN
2.1 INTRODUCTION 49
2.2 ALKYLATION BY RUTHENIUM(O) CATALYSTS VIA OXIDATIVE-ADDITION C-H
ACTIVATION 50
2.2.1 ALKYLATION BY RUTHENIUM(II) CATALYSTS VIA CARBOXYLATE-ASSISTED C-H
ACTIVATION 63
2.3 SUMMARY AND CONCLUSIONS 70
ABBREVIATIONS 71
REFERENCES 71
3 ALKYLATION OF ARENES WITHOUT CHELATION ASSISTANCE: TRANSITION
METAL CATALYSTS WITH D6 ELECTRON CONFIGURATIONS
83
BRADLEY A. MCKEOWN, LAUREL GOJ HABGOOD, THOMAS
/?.
CUNDARI, AND
T BRENT GUNNOE
3.1 TRANSITION METAL-MEDIATED ARENE ALKYLATION: OVERVIEW 83
3.2 OCTAHEDRAL D6 TRANSITION METAL CATALYSTS FOR OLEFIN HYDROARYLATION:
SCORPIONATE SUPPORTED RU(II) CATALYSTS 85
3.2.1 STRUCTURE-ACTIVITY RELATIONSHIPS WITH TPRU(L)(NCME)PH:
EXAMINATION OF ELEMENTARY STEPS AND CATALYTIC HYDROPHENYLATION OF
ETHYLENE AS A FUNCTION OF LIGAND L 90
3.2.2 ETHYLENE HYDROPHENYLATION CATALYZED BY CATIONIC RU(II) COMPLEXES
LIGATED BY POLY(PYRAZOLYL)ALKANES 93
3.3 OLEFIN HYDROARYLATION CATALYZED BY OCTAHEDRAL D6 IR(III) SUPPORTED
BY
THE ACETYLACETONATE LIGAND 95
3.3.1 MECHANISM OF CATALYTIC OLEFIN HYDROPHENYLATION USING IR(III)
SUPPORTED BY THE ACETYLACETONATE LIGAND 96
3.3.2 OTHER D6 IR(III) CATALYSTS 98
3.4 SUMMARY: COMPARISON OF RU(II) AND IR(III) CATALYSTS FOR OLEFIN
HYDROARYLATION 99
3.5 FUTURE OUTLOOK: EXTENSION OF OLEFIN HYDROARYLATION USING
HYDROCARBONS TO EARTH ABUNDANT METALS 100
REFERENCES 102
4 HYDROARYLATION OF OLEFINS WITH COMPLEXES BEARING D8 METAL
CENTERS
107
BENJAMIN A. SUSLICK AND T. DON TILLEY
4.1 INTRODUCTION 107
4.2 PTN CATALYZED HYDROARYLATION 109
4.2.1 PTN HYDROARYLATION CATALYSTS BEARING ANIONIC BIDENTATE (NN)
LIGANDS 109
4.2.2 PT11 HYDROARYLATION CATALYSTS BEARING NEUTRAL BIDENTATE (NN)
LIGANDS 114
4.2.3 PT11 HYDROARYLATION CATALYSTS SUPPORTED BY NONNITROGEN-BASED
LIGANDS 119
4.2.4 SUMMARY OF PT11 CATALYZED HYDROARYLATIONS 123
4.3 RH1-CATALYZED HYDROARYLATION 124
4.3.1 REACTIONS OF UNFUNCTIONALIZED ARENES WITH RH1 COMPLEXES PROCEEDING
VIA HYDROARYLATION-LIKE MECHANISMS 124
4.3.2 DIRECTED ORTHO-HYDROARYLATION CATALYZED BY RH1 COMPLEXES 126
4.3.3 RH1-CATALYZED HYDROARYLATION WITH FLUORINATED ARENES 142
4.3.4 SUMMARY OF RH1-CATALYZED HYDROARYLATION 142
4.4 DIRECTED ORTHO-HYDROARYLATION CATALYZED BY IR1 COMPLEXES 144
4.5 HYDROARYLATION WITH NI COMPLEXES VIA NI11 INTERMEDIATES 152
4.6 FORMAL HYDROARYLATION REACTIONS WITH PD11 CATALYSTS VIA HECK-LIKE
MECHANISMS 155
4.6.1 FORMATE-ASSISTED PD11 CATALYZED HYDROARYLATION 155
4.6.2 OXIDATIVELY COUPLED PDU-CATALYZED HYDROARYLATION WITH ARYLTIN AND
ARYLBORONIC ESTER SUBSTRATES 160
4.6.3 SUMMARY OF PDN-CATALYZED FORMAL HYDROARYLATION REACTIONS 163
4.7 CONCLUSIONS 166
REFERENCES 166
5 HYDROARYLATION OF C-C MULTIPLE BONDS USING NICKEL
CATALYSTS
175
YOSHIAKI NOKAO
5.1 INTRODUCTION 175
5.2 HYDROARYLATION OF ALKYNES 175
5.3 HYDROHETEROARYLATION OF ALKYNES 179
5.3.1 HYDROHETEROARYLATION OF ALKYNES WITH FIVE-MEMBERED
HETEROARENES 179
5.3.2 HYDROHETEROARYLATION OF ALKYNES WITH AZINE-AT-OXIDES 182
5.3.3 HYDROHETEROARYLATION OF ALKYNES WITH AZINES 182
5.4 HYDROARYLATION OF ALKENES 184
5.5 HYDROHETEROARYLATION OF ALKENES 185
5.5.1 HYDROHETEROARYLATION OF ALKENES WITH FIVE-MEMBERED
HETEROARENES 185
5.5.2 HYDROHETEROARYLATION OF ALKENES WITH AZINES 188
5.6 SUMMARY AND OUTLOOK 189
REFERENCES 190
6 HYDROARYLATION OF ALKYNES AND ALKENES USING GROUP 7-9
FIRST-ROW TRANSITION METAL CATALYSTS
193
NAOHIKO YOSHIKAI
6.1 INTRODUCTION 193
6.2 HYDROARYLATION OF ALKYNES AND ALKENES USING COBALT CATALYSTS 194
6.2.1 HYDROARYLATION OF ALKYNES USING LOW-VALENT COBALT CATALYSTS 194
6.2.2 HYDROARYLATION OF ALKENES USING LOW-VALENT COBALT CATALYSTS 199
6.2.3 HYDROARYLATION OF ALKYNES AND ALKENES USING CP*COM CATALYSTS 206
6.3 HYDROARYLATION OF ALKYNES AND ALKENES USING IRON CATALYSTS 208
6.3.1 HYDROARYLATION OF ALKYNES AND ALKENES USING LOW-VALENT IRON
CATALYSTS 208
6.3.2 HYDROARYLATION OF ALKENES USING LEWIS ACIDIC IRON CATALYSTS 208
6.4 HYDROARYLATION OF ALKYNES USING LOW-VALENT MANGANESE
CATALYST 209
6.5 CONCLUSIONS 211
6.6 ABBREVIATIONS 211
REFERENCES 212
7
HYDROARYLATION OF ALKYNES USING CU, AG, AND AU CATALYSTS
217
MARIIA
5. KIRILLOVA
,
FEDOR M. MILOSERDOV, AND ANTONIO M. ECHAVARREN
7.1 INTRODUCTION 217
7.2 INTRAMOLECULAR HYDROARYLATION OF ALKYNES 218
7.2.1 ALKYNE HYDROARYLATION WITH ELECTRON-RICH ARENES 218
7.2.1.1 ALKYNE HYDROARYLATION WITH ANILINE DERIVATIVES 218
7.2.1.2 ALKYNE HYDROARYLATION WITH PHENOLS AND PHENOL ETHER
DERIVATIVES 225
7.2.2 ALKYNE HYDROARYLATION WITH OTHER ARENES 231
7.2.3 ALKYNE HYDROARYLATION WITH INDOLES 237
7.2.3.1 ALKENYLATION OF INDOLES AT THE 2-POSITION 239
7.2.3.2 ALKENYLATION OF INDOLES AT THE 3-POSITION 242
7.2.3.3 SPIROCYCLIZATIONS 244
7 2 3 A
MORE COMPLEX TRANSFORMATIONS FEATURING A HYDROARYLATION OF
ALKYNES 246
7.2.4 ALKYNE HYDROARYLATION WITH PYRROLES 258
7.2.5 ALKYNE HYDROARYLATION WITH FURANS AND BENZOFURANS 263
7.2.5.1 ALKENYLATION AT THE 2-POSITION OF FURAN 264
7 2 3 2 ALKENYLATION AT THE 3-POSITION OF FURAN 265
7 2 3 3 MORE COMPLEX TRANSFORMATIONS FEATURING HYDROARYLATION OF
ALKYNES 265
7 2 3 A
THE FURAN-YNE CYCLOISOMERIZATION TO PHENOLS 270
7.2.6 ALKYNE HYDROARYLATION WITH THIOPHENES AND BENZOTHIOPHENES 276
7.3 INTERM ODULAR HYDROARYLATION OF ALKYNES 277
7.3.1 INTERM ODULAR HYDROARYLATION OF ALKYNES WITH ARENES 277
7.3.2 INTERM ODULAR HYDROARYLATION OF ALKYNES WITH HETEROARENES 278
7.3.2.1 AF-HETEROCYCLES 279
7 3 2 2
O-HETEROCYCLES 282
7.4 METAL-SUPPORTED CATALYSTS AND THEIR APPLICATIONS IN HYDROARYLATION
OF ALKYNES 284
7.5 HYDROARYLATION OF ALKYNES IN TOTAL SYNTHESIS 288
REFERENCES 291
8 CATALYTIC ALKYNE HYDROARYLATION USING ARYLBORON REAGENTS,
ARYL HALIDES, AND CONGENERS
305
YOSHIHIKO YAMAMOTO
8.1 INTRODUCTION 305
8.2 CATALYZED ALKYNE HYDROARYLATIONS USING ARYLBORON AND ARYLSILICON
REAGENTS 307
8.2.1 RHODIUM-CATALYZED REACTIONS 308
8.2.2 PALLADIUM-CATALYZED REACTIONS 315
8.2.3 REACTIONS CATALYZED BY FIRST ROW TRANSITION METALS 321
8.3 CATALYZED ALKYNE HYDROARYLATIONS USING ARYL HALIDES AND
ARENEDIAZONIUM COMPOUNDS 326
8.3.1 INTERM ODULAR REDUCTIVE HECK REACTIONS 327
8.3.2 INTRAMOLECULAR REDUCTIVE HECK REACTIONS 333
8.4 SYNTHETIC APPLICATIONS OF ALKYNE HYAROARYLATIONS USING ARYLBORON
REAGENTS AND ARYL HALIDES 336
8.4.1 SEQUENTIAL PROCESSES INVOLVING ALKYNE HYDROARYLATIONS USING
ARYLBORON REAGENTS AND ARYL HALIDES 336
8.4.1.1 SYNTHESIS OF OXYGEN HETEROCYCLES 336
8.4.1.2 SYNTHESIS OF NITROGEN AND PHOSPHOROUS HETEROCYCLES 341
8.4.1.3 SYNTHESIS OF CARBOCYCLES 346
8.4.2
SYNTHESIS OF BIOACTIVE COMPOUNDS AND NATURAL PRODUCTS VIA ALKYNE
HYDROARYLATIONS USING ARYLBORON REAGENTS AND ARYL HALIDES 348
8.5 SUMMARY 352
REFERENCES 354
9 TRANSITION METAL-CATALYZED HYDROARYLATION OF ALLENES
361
ROSS A. WIDENHOEFER
9.1 INTRODUCTION 361
9.2 INTRAMOLECULAR HYDROARYLATION 362
9.2.1 INDOLES AS NUCLEOPHILES 362
9.2.1.1 6-E#O-HYDROARYLATION 362
9.2.1.2 5-E#O-HYDROARYLATION 363
9.2.1.3 6-ETFDO-HYDROARYLATION 364
9.2.1.4 5-EFLTIFO-HYDROARYLATION 365
9.2.1.5 LESS COMMON MODES OF RING CLOSURE 367
9.2.2 OTHER NUCLEOPHILES 368
9.2.2.1 6-6-CO-HYDROARYLATION 368
9.2.2.2 6-EFLTIFO-HYDROARYLATION 373
9.2.2.Z LESS COMMON MODES OF RING CLOSURE 376
9.3 INTERMOLECULAR HYDROARYLATION 378
9.3.1 INDOLES AS NUCLEOPHILES 378
9.3.1.1 MONOADDITION PROCESSES 378
9.3.1.2 TANDEM ADDITION PROCESSES 378
9.3.2 FURANS AS NUCLEOPHILES 379
9.3.3 ALKOXY BENZENES AS NUCLEOPHILES 381
9.3.4 ALKYL BENZENES AS NUCLEOPHILES 383
9.4 ENANTIOSELECTIVE HYDROARYLATION 384
9.4.1 INTRAMOLECULAR HYDROARYLATION 384
9.4.2 INTERMOLECULAR HYDROARYLATION 384
9.5 SUMMARY AND OUTLOOK 385
REFERENCES 386
INDEX
389
|
| any_adam_object | 1 |
| author2 | Ackermann, Lutz 1972- Gunnoe, T. Brent Goj Habgood, Laurel |
| author2_role | edt edt edt |
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| author_GND | (DE-588)123337976 (DE-588)1150719877 (DE-588)1150722436 |
| author_facet | Ackermann, Lutz 1972- Gunnoe, T. Brent Goj Habgood, Laurel |
| building | Verbundindex |
| bvnumber | BV044675032 |
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| ctrlnum | (OCoLC)1019888633 (DE-599)DNB1130802620 |
| dewey-full | 540 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 540 - Chemistry and allied sciences |
| dewey-raw | 540 |
| dewey-search | 540 |
| dewey-sort | 3540 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
| format | Book |
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| genre | (DE-588)4143413-4 Aufsatzsammlung gnd-content |
| genre_facet | Aufsatzsammlung |
| id | DE-604.BV044675032 |
| illustrated | Illustrated |
| indexdate | 2024-07-10T07:59:00Z |
| institution | BVB |
| institution_GND | (DE-588)16179388-5 |
| isbn | 9783527340132 3527340130 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-030072327 |
| oclc_num | 1019888633 |
| open_access_boolean | |
| owner | DE-703 DE-11 DE-19 DE-BY-UBM DE-83 |
| owner_facet | DE-703 DE-11 DE-19 DE-BY-UBM DE-83 |
| physical | ix, 403 Seiten Illustrationen |
| publishDate | 2018 |
| publishDateSearch | 2018 |
| publishDateSort | 2018 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Catalytic hydroarylation of carbon-carbon multiple bonds edited by Lutz Ackermann, T. Brent Gunnoe, Laurel Goj Habgood Weinheim, Germany Wiley-VCH [2018] © 2018 ix, 403 Seiten Illustrationen txt rdacontent n rdamedia nc rdacarrier Kohlenstoff-Kohlenstoff-Bindung (DE-588)4164549-2 gnd rswk-swf Mehrfachbindung (DE-588)4317639-2 gnd rswk-swf Katalyse (DE-588)4029921-1 gnd rswk-swf Heteroaromaten (DE-588)4159717-5 gnd rswk-swf Aromaten (DE-588)4143049-9 gnd rswk-swf Hydroarylierung (DE-588)4251821-0 gnd rswk-swf Catalysis Chemie Chemistry Hydroarylierung Industrial Chemistry Katalyse Nanomaterialien Nanomaterials Nanotechnologie Nanotechnology Pharmaceutical & Medicinal Chemistry Pharmazeutische u. Medizinische Chemie Polymer Science & Technology Polymer Synthesis Polymersynthese Polymerwissenschaft u. -technologie Technische u. Industrielle Chemie (DE-588)4143413-4 Aufsatzsammlung gnd-content Aromaten (DE-588)4143049-9 s Hydroarylierung (DE-588)4251821-0 s Katalyse (DE-588)4029921-1 s DE-604 Heteroaromaten (DE-588)4159717-5 s Mehrfachbindung (DE-588)4317639-2 s Kohlenstoff-Kohlenstoff-Bindung (DE-588)4164549-2 s Ackermann, Lutz 1972- (DE-588)123337976 edt Gunnoe, T. Brent (DE-588)1150719877 edt Goj Habgood, Laurel (DE-588)1150722436 edt Wiley-VCH (DE-588)16179388-5 pbl Erscheint auch als Online-Ausgabe, PDF 978-3-527-69763-2 Erscheint auch als Online-Ausgabe, EPUB 978-3-527-69765-6 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-69766-3 Erscheint auch als Online-Ausgabe, OBOOK 978-3-527-69764-9 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030072327&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Catalytic hydroarylation of carbon-carbon multiple bonds Kohlenstoff-Kohlenstoff-Bindung (DE-588)4164549-2 gnd Mehrfachbindung (DE-588)4317639-2 gnd Katalyse (DE-588)4029921-1 gnd Heteroaromaten (DE-588)4159717-5 gnd Aromaten (DE-588)4143049-9 gnd Hydroarylierung (DE-588)4251821-0 gnd |
| subject_GND | (DE-588)4164549-2 (DE-588)4317639-2 (DE-588)4029921-1 (DE-588)4159717-5 (DE-588)4143049-9 (DE-588)4251821-0 (DE-588)4143413-4 |
| title | Catalytic hydroarylation of carbon-carbon multiple bonds |
| title_auth | Catalytic hydroarylation of carbon-carbon multiple bonds |
| title_exact_search | Catalytic hydroarylation of carbon-carbon multiple bonds |
| title_full | Catalytic hydroarylation of carbon-carbon multiple bonds edited by Lutz Ackermann, T. Brent Gunnoe, Laurel Goj Habgood |
| title_fullStr | Catalytic hydroarylation of carbon-carbon multiple bonds edited by Lutz Ackermann, T. Brent Gunnoe, Laurel Goj Habgood |
| title_full_unstemmed | Catalytic hydroarylation of carbon-carbon multiple bonds edited by Lutz Ackermann, T. Brent Gunnoe, Laurel Goj Habgood |
| title_short | Catalytic hydroarylation of carbon-carbon multiple bonds |
| title_sort | catalytic hydroarylation of carbon carbon multiple bonds |
| topic | Kohlenstoff-Kohlenstoff-Bindung (DE-588)4164549-2 gnd Mehrfachbindung (DE-588)4317639-2 gnd Katalyse (DE-588)4029921-1 gnd Heteroaromaten (DE-588)4159717-5 gnd Aromaten (DE-588)4143049-9 gnd Hydroarylierung (DE-588)4251821-0 gnd |
| topic_facet | Kohlenstoff-Kohlenstoff-Bindung Mehrfachbindung Katalyse Heteroaromaten Aromaten Hydroarylierung Aufsatzsammlung |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030072327&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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