Palladium-catalyzed coupling reactions: practical aspects and future developments
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Wiley-VCH
2013
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Beschreibung: | XIX, 511 S. graph. Darst. 230 mm x 170 mm |
ISBN: | 3527332545 9783527332540 |
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IMAGE 1
CONTENTS
FOREWORD XIII PREFACE X V LIST OF CONTRIBUTORS XVII
1 PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS - A GENERAL INTRODUCTION
1 KLAUS KOHLER, KATHARINA WUSSOW, AND ANDREAS SEBASTIAN WIRTH 1.1
INTRODUCTION 1
1.1.1 HISTORICAL REFLECTION 1
1.1.2 CHARACTERISTICS, RECENT DEVELOPMENTS, AND PROGRESS 2 1.1.3
LITERATURE REVIEWS AND ORGANIZATION O F THE CHAPTER 3 1.2 CARBON-CARBON
CROSS-COUPLING REACTIONS CATALYZED BY PALLADIUM 4
1.2.1 CLASSIFICATION AND OVERVIEW 4 1.2.2 COMMON MECHANISTIC FEATURES OF
CROSS-COUPLING REACTIONS AND REACTIVITY OF THE SUBSTRATES 8 1.2.2.1
CHOICE O F THE CARBON ELECTROPHILE 9
1.2.2.2 CHOICE OF THE CARBON NUCLEOPHILE - WHAT MAKES THE DIFFERENCE? 9
1.3 THE CATALYSTS 10
1.3.1 THE PARTICULAR FEATURES OF PALLADIUM 10 1.3.2 CLASSES OF PALLADIUM
CATALYSTS APPLIED TO CROSS-COUPLING REACTIONS 12 1.3.2.1 IIGANDS AND
PALLADIUM COMPLEXES - HOMOGENEOUS SYSTEMS 13
1.3.2.2 IMMOBILIZED OR SUPPORTED PALLADIUM COMPLEXES AND PARTICLES -
HETEROGENEOUS SYSTEMS 17 1.3.2.3 PALLADIUM COLLOIDS AND (NONSUPPORTED)
NANOPARTICLES 17 1.3.2.4 ACTIVITY O F HETEROGENEOUS CATALYSTS 18 1.4
MECHANISTIC ASPECTS 18
1.4.1 GENERAL MECHANISM O F C-C CROSS-COUPLING AND HECK REACTIONS WITH
HOMOGENEOUS CATALYST PRECURSORS 18 1.4.2 MODELS FOR HECK AND SUZUKI
REACTIONS WITH SUPPORTED PD PRECURSORS 19 1.4.3 RECENT RESULTS ON THE
REACTION MECHANISM AND THE NATURE O F THE
ACTIVE PD SPECIES 21
HTTP://D-NB.INFO/1027115918
IMAGE 2
V I I CONTENTS
1.4.3.1 OBSERVATION O F INTERMEDIATES IN HOMOGENEOUS CATALYSIS BY
ELECTROCHEMICAL METHODS 21 1.4.3.2 THE QUESTION O F PD LEACHING 22
1.4.3.3 SELECTIVITY PATTERN 23 1.4.3.4 IN SITU OBSERVATION BY
SPECTROSCOPIC METHODS 24 1.4.3.5 IMMOBILIZED PD PINCER COMPLEXES 24
1.4.3.6 PALLADIUM BULK MATERIALS (PD FOIL, WIRE, SPONGE) AS CATALYST 24
1.5 FUTURE CHALLENGES 25
ABBREVIATIONS 27 REFERENCES 27
2 HIGH-TURNOVER HETEROGENEOUS PALLADIUM CATALYSTS IN COUPLING REACTIONS:
THE CASE O F PD LOADED ON DEALUMINATED Y ZEOLITES 31 KAZU OKUMURA 2.1
INTRODUCTION 31
2.2 VARIOUS METHODOLOGIES TO AFFORD HIGH TURNOVER NUMBERS OVER SUPPORTED
PD CATALYSTS 32 2.3 STRUCTURE AND CHARACTERISTICS OF ULTRASTABLE Y
ZEOLITES 33 2.4 SUZUKI-MIYAURA REACTIONS CATALYZED BY PD/USY 35
2.4.1 CATALYTIC PERFORMANCE O F PD/USY 35 2.4.2 PD LEACHING FROM PD/USY
40 2.4.3 SELECTIVITY IN THE HOMOCOUPLING REACTIONS 41 2.4.4
CHARACTERIZATION O F THE ACTIVE PD SPECIES BY X-RAY ABSORPTION
SPECTROSCOPY 41
2.4.5 A SUGGESTED MECHANISM FOR THE FORMATION O F ACTIVE PD SPECIES IN
SUZUKI-MIYAURA COUPLING REACTIONS 46 2.5 CATALYTIC PERFORMANCE OF PD/USY
I N MIZOROKI-HECK REACTIONS 48 2.5.1 EFFECT O F H 2 BUBBLING ON THE
CATALYTIC REACTIONS O F PD/USY 48
2.5.2 CATALYTIC REACTIONS USING CHLOROBENZENE DERIVATIVES 51 2.5.3
CHARACTERIZATION O F THE PD SPECIES BY X-RAY ABSORPTION SPECTROSCOPY 53
2.6 CONCLUSION AND PERSPECTIVE 54
ABBREVIATIONS 55 REFERENCES 55
3 PALLADIUM-CATALYZED COUPLING REACTIONS WITH MAGNETICALLY SEPARABLE
NANOCATALYSTS 57 KIFAH S.M. SALIH AND WERNER R. THIEL 3.1 INTRODUCTION
57
3.2 GENERAL CONSIDERATIONS CONCERNING MAGNETIC PARTICLES AS CATALYST
SUPPORTS 57 3.3 PALLADIUM NANOPARTICLES ON MAGNETIC SUPPORTS 59 3.4
MOLECULAR PALLADIUM COMPLEXES ON MAGNETIC SUPPORTS 68
3.5 OUTLOOK 75
IMAGE 3
CONTENTS I V I I
ABBREVIATIONS 76
REFERENCES 77
4 THE USE O F ORDERED POROUS SOLIDS AS SUPPORT MATERIALS IN
PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS 79 ARPAD MOLNAR 4.1
INTRODUCTION 79
4.2 CATALYST SYNTHESIS AND CHARACTERIZATION 80 4.3 CARBON-CARBON
COUPLINGS 85
4.3.1 ZEOLITES 85
4.3.2 MESOPOROUS ORDERED SILICA MATERIALS 94 4.3.2.1 COUPLING REACTIONS
CATALYZED BY SUPPORTED PALLADIUM PARTICLES 94 4.3.2.2 REACTIONS MEDIATED
BY IMMOBILIZED PALLADIUM SPECIES 103 4.3.3 PERIODIC MESOPOROUS
ORGANOSILICAS 116 4.3.4 CATALYSTS BASED ON NONSILICEOUS SOLIDS 121
4.3.4.1 METAL-ORGANIC FRAMEWORKS 121 4.3.4.2 COVALENT ORGANIC FRAMEWORKS
123 4.3.4.3 OTHER SUPPORT MATERIALS 124 4.4 MISCELLANEOUS COUPLING
REACTIONS 127 4.5 THE QUESTION O F SOLUTION-PHASE CATALYSIS 130 4.6
SUMMARY AND FUTURE PROSPECTS 131
ABBREVIATIONS 133 REFERENCES 134
5 COUPLING REACTIONS INDUCED BY POLYMER-SUPPORTED CATALYSTS 141 BABAK
KARIMI, SEDIGHEH ABEDI, AND ASGHAR ZAMANL 5.1 INTRODUCTION 141
5.2 POLYSACCHARIDES 143
5.2.1 STARCH 143
5.2.2 CHITOSAN 145
5.2.3 OTHER POLYSACCHARIDES 148 5.3 POLY(ETHYLENE GLYCOL) 150
5.3.1 NONFUNCTIONALIZED POLY(ETHYLENE GLYCOL) 150 5.3.2 FUNCTIONALIZED
POLY(ETHYLENE GLYCOL) 152 5.4 POLYSTYRENE 155
5.4.1 NONFUNCTIONALIZED POLYSTYRENE 155 5.4.2 FUNCTIONALIZED POLYSTYRENE
156 5.4.2.1 POLYSTYRENE-SUPPORTED LIGANDS CONTAINING NITROGEN 156
5.4.2.2 POLYSTYRENE-SUPPORTEDTRIPHENYLPHOSPHANE 161
5.5 POLY(NORBORNENE) 165
5.6 POLYACRYLAMIDE 167
5.7 POLYANILINE 170
5.8 POLY(N-VINYL-2-PYRROLIDONE) 171 5.9 POLYPYRROLE 173
5.10 POLY(4-VINYLPYRIDINE) 174
IMAGE 4
V I I I | CONTENTS
5.11 IONIC POLYMERS 175
5.11.1 ORGANIC POLYMERS CONTAINING N-HETEROCYCLIC CARBENES OR IONIC
LIQUIDS 176 5.11.2 POLYMERS CONTAINING OTHER IONIC IIGANDS 183 5.12
ORGANOMETALLIC POLYMERS 184
5.13 FUNCTIONALIZED POROUS ORGANIC POLYMERS 188 5.14 MISCELLANEOUS
POLYMERS 189 5.15 SUMMARY AND OUTLOOK 192
ABBREVIATIONS 193 REFERENCES 195
6 COUPLING REACTIONS IN IONIC LIQUIDS 201
MICHAEL T. KEFILER, JACKSON D. SCHOLTEN, FRANK CALBRECHT, AND MARTIN
H.C. PRECHTL 6.1 INTRODUCTION 201
6.2 METAL COMPLEXES 204
6.2.1 MIZOROKI-HECK REACTION 205 6.2.2 SONOGASHIRA COUPLING 209 6.2.3
SUZUKI-MIYAURA COUPLING 212 6.2.4 NEGISHI COUPLING 213
6.2.5 TROST-TSUJI COUPLING 214 6.3 METAL SALTS AND METAL ON SOLID
SUPPORT 214 6.3.1 MIZOROKI-HECK REACTION 215 6.3.2 SUZUKI-MIYAURA
REACTION 218 6.3.3 STILLE REACTION 219
6.4 METAL NANOPARTICLES 220
6.4.1 THE MIZOROKI-HECK REACTION WITH PDNPS IN ILS 222 6.4.2
SUZUKI-MIYAURA REACTION 224 6.4.3 STILLE REACTION 226
6.4.4 BUCHWALD-HARTWIG REACTION 227 6.4.5 SONOGASHIRA REACTION 228 6.4.6
ULLMANN REACTION 228
6.5 SUMMARY AND OUTLOOK 229
ABBREVIATIONS 230 REFERENCES 231
7 CROSS-COUPLING REACTIONS IN AQUEOUS MEDIA 235 KEVIN H. SHAUGHNESSY 7.1
INTRODUCTION 235
7.2 CROSS-COUPLING O F ORGANIC HALIDES TO FORM C-C BONDS IN AQUEOUS
MEDIA 236 7.2.1 SUZUKI COUPLING 236
7.2.1.1 AQUEOUS-PHASE SUZUKI COUPLING USING HYDROPHILIC LIGAND-SUPPORTED
CATALYSTS 237 7.2.1.2 ON WATER SUZUKI COUPLINGS WITH HYDROPHOBIC
CATALYST SYSTEMS 248
IMAGE 5
CONTENTS I X
7.2.1.3 SURFACTANT-PROMOTED AQUEOUS-PHASE SUZUKI COUPLINGS 249
7.2.1.4 PALLADIUM CATALYSTS SUPPORTED ON HETEROGENEOUS SUPPORTS 251
7.2.1.5 PALLADIUM NANOPARTICLE CATALYSTS 253 7.2.2 STILLE COUPLING 256
7.2.3 HIYAMA COUPLING 257
7.2.4 NEGISHI COUPLING 259
7.2.5 SONOGASHIRA COUPLING 260 7.2.6 ARYLATION OF OTHER CARBANION
NUCLEOPHILES 268 7.2.7 HECK COUPLING 270
7.3 CARBON-HETEROATOM COUPLING REACTIONS 274 7.3.1 AMINATION O F ARYL
HALIDES 274 7.3.2 OTHER CARBON-HETEROATOM COUPLING REACTIONS 276 7.4 C-H
ACTIVATION IN AQUEOUS MEDIA 277
7.5 CONCLUSION AND FUTURE PROSPECTS 279
ABBREVIATIONS 279 REFERENCES 281
8 MICROWAVE-ASSISTED SYNTHESIS IN C-C AND CARBON-HETEROATOM COUPLING
REACTIONS 287 KE-HU WANG ANDJIN-XIAN WANG 8.1 INTRODUCTION 287
8.2 C-C BOND FORMATION 288
8.2.1 HECK COUPLING REACTIONS 288 8.2.2 SUZUKI REACTIONS 295
8.2.3 NEGISHI COUPLINGS 308
8.2.4 COUPLING O F TERMINAL ALKYNES WITH ARYL HALIDES 310 8.2.5 COUPLING
REACTIONS OF ORGANOSTANNANES WITH ORGANIC HALIDES 312 8.2.6 COUPLINGS O
F ORGANOSILANES WITH ARYL HALIDES 313 8.2.7 CYANATION O F ARYL HALIDES
315
8.2.8 CARBONYLATION REACTIONS 316 8.2.9 DECARBOXYLATIVE COUPLINGS 318
8.2.10 OTHER C-C BOND FORMATIONS 319 8.3 C-X BOND FORMATION 321
8.3.1 C-N BOND FORMATION 321 8.3.2 C-P BOND FORMATION 325 8.4
CONCLUSIONS 327
ABBREVIATIONS 327 REFERENCES 328
9 CATALYST RECYCLING IN PALLADIUM-CATALYZED CARBON-CARBON COUPLING
REACTIONS 333 ARPAD MOLNAR 9.1 INTRODUCTION 333
9.2 GENERAL ISSUES OF CATALYST RECYCLING 333 9.3 CATALYST SYSTEMS
PROVIDING HIGH, CONSISTENT YIELDS I N RECYCLING 337
IMAGE 6
X I CONTENTS
9.3.1 THE USE O F CATALYSTS WITH PD PARTICLES 337
9.3.2 RECYCLING O F PALLADIUM COMPLEXES 346 9.3.2.1 COMPLEXES ANCHORED
TO INORGANIC SUPPORTS 346 9.3.2.2 COMPLEXES IMMOBILIZED ON POLYMERS 355
9.3.2.3 SELF-SUPPORTED POLYMERIC COMPLEXES 361 9.3.3 STUDIES PERFORMED
UNDER HOMOGENEOUS CONDITIONS 362 9.4 CATALYSTS AFFORDING THE HIGHEST
CUMULATIVE TON VALUES IN RECYCLING STUDIES 370 9.4.1 CATALYSTS WITH
SUPPORTED PARTICLES 370
9.4.2 IMMOBILIZED COMPLEXES 373 9.5 SUMMARY EVALUATION 375
9.6 FUTURE OUTLOOK 381
ABBREVIATIONS 382 REFERENCES 383
T O NATURE O F THE TRUE CATALYTIC SPECIES IN CARBON-CARBON COUPLING
REACTIONS WITH HETEROGENEOUS PALLADIUM PRECATALYSTS 387 LIN HUANG AND
PUI KWAN WONG 10.1 INTRODUCTION 387
10.2 HECK REACTIONS 389
10.2.1 SUPPORTED PD PARTICLES 389 10.2.2 IMMOBILIZED PD COMPLEXES 394
10.3 SUZUKI REACTIONS 396
10.3.1 SUPPORTED PD PARTICLES 396 10.3.2 IMMOBILIZED PD COMPLEXES 398
10.4 SONOGASHIRA REACTIONS 402 10.4.1 SUPPORTED PD PARTICLES 402 10.4.2
IMMOBILIZED PD COMPLEXES 403 10.5 CONCLUDING REMARKS 404
ABBREVIATIONS 406 REFERENCES 406
11 COUPLING REACTIONS IN CONTINUOUS-FLOW SYSTEMS 409 WILLIAM R. REYNOLDS
AND CHRISTOPHER C. FROST 11.1 INTRODUCTION 409
11.2 COUPLING REACTIONS IN FLOW 410 11.2.1 SUZUKI-MIYAURA COUPLING 410
11.2.2 MIZOROKI-HECK COUPLING 413 11.2.3 SONOGASHIRA COUPLING 415
11.2.4 MURAHASHI COUPLING 416 11.2.5 HIYAMA COUPLING 418 11.2.6
CARBONYLATIVE COUPLINGS 418 11.2.7 BUCHWALD-HARTWIG AMINATION 420
11.3 PALLADIUM CATALYSTS FOR FLOW SYSTEMS 422 11.3.1 HETEROGENEOUS
SUPPORTED CATALYSTS 422
IMAGE 7
CONTENTS | X I
11.3.1.1 PALLADIUM ON CHARCOAL 422
11.3.1.2 PDENCAT 424 11.3.1.3 SILICON DIOXIDE SUPPORTS 425 11.3.1.4
POLYMERIC SUPPORTS 426 11.3.1.5 MAGNETIC NANOPARTICLES 427 11.3.1.6
MONOLITHIC SUPPORTS 428 11.3.2 HOMOGENEOUS CATALYSTS 431 11.3.2.1
SINGLE-PHASE REACTIONS 431 11.3.2.2 BIPHASIC SYSTEMS 433 11.4
CONTINUOUS-FLOW TECHNOLOGIES FOR CROSS-COUPLING 435
11.4.1 MICROREACTORS 435 11.4.2 MICROWAVE-ASSISTED CONTINUOUS-FLOW
ORGANIC SYNTHESIS 436 11.4.3 TOWARD SEQUENTIAL COUPLING REACTIONS IN
FLOW 438 11.5 SUMMARY AND OUDOOK 438
ABBREVIATIONS 440 REFERENCES 440
12 PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS - INDUSTRIAL
APPLICATIONS 445 ANDREAS DUMRATH, CHRISTA LUBBE, AND MATTHIAS BELTER
12.1 INTRODUCTION 445
12.2 SUZUKI-MIYAURA REACTIONS 447 12.3 HECK-MIZOROKI REACTIONS 459 12.4
SONOGASHIRA-HAGIHARA REACTIONS 463 12.5 CARBONYLATIONS 469
12.6 CYANATIONS 471
12.7 NEGISHI COUPLING 474
12.8 NOVEL PD-CATALYZED C-C CROSS-COUPLING REACTION 475 12.9
BUCHWALD-HARTWIG ANIMATIONS 475 12.10 PD-CATALYZED C-S BOND FORMATION
478 12.11 SUMMARY AND OUTLOOK 479
ACKNOWLEDGMENTS 480 ABBREVIATIONS 480 REFERENCES 481
INDEX 491 |
any_adam_object | 1 |
author2 | Molnár, Árpád 1942- |
author2_role | edt |
author2_variant | á m ám |
author_GND | (DE-588)172903017 |
author_facet | Molnár, Árpád 1942- |
building | Verbundindex |
bvnumber | BV040972873 |
classification_rvk | VH 8088 VK 5500 VK 7788 |
classification_tum | CHE 620f CHE 376f |
ctrlnum | (OCoLC)854695446 (DE-599)DNB1027115918 |
dewey-full | 547.215 |
dewey-hundreds | 500 - Natural sciences and mathematics |
dewey-ones | 547 - Organic chemistry |
dewey-raw | 547.215 |
dewey-search | 547.215 |
dewey-sort | 3547.215 |
dewey-tens | 540 - Chemistry and allied sciences |
discipline | Chemie / Pharmazie Chemie |
format | Book |
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genre | (DE-588)4143413-4 Aufsatzsammlung gnd-content |
genre_facet | Aufsatzsammlung |
id | DE-604.BV040972873 |
illustrated | Illustrated |
indexdate | 2024-08-03T00:37:23Z |
institution | BVB |
isbn | 3527332545 9783527332540 |
language | English |
oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-025951028 |
oclc_num | 854695446 |
open_access_boolean | |
owner | DE-11 DE-91G DE-BY-TUM DE-29T DE-19 DE-BY-UBM |
owner_facet | DE-11 DE-91G DE-BY-TUM DE-29T DE-19 DE-BY-UBM |
physical | XIX, 511 S. graph. Darst. 230 mm x 170 mm |
publishDate | 2013 |
publishDateSearch | 2013 |
publishDateSort | 2013 |
publisher | Wiley-VCH |
record_format | marc |
spelling | Palladium-catalyzed coupling reactions practical aspects and future developments ed. by Árpád Molnár Weinheim Wiley-VCH 2013 XIX, 511 S. graph. Darst. 230 mm x 170 mm txt rdacontent n rdamedia nc rdacarrier Katalyse (DE-588)4029921-1 gnd rswk-swf Palladiumverbindungen (DE-588)4173148-7 gnd rswk-swf Kupplungsreaktion (DE-588)4166199-0 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Kupplungsreaktion (DE-588)4166199-0 s Katalyse (DE-588)4029921-1 s Palladiumverbindungen (DE-588)4173148-7 s DE-604 Molnár, Árpád 1942- (DE-588)172903017 edt text/html http://deposit.dnb.de/cgi-bin/dokserv?id=4166021&prov=M&dok_var=1&dok_ext=htm Inhaltstext DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025951028&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
spellingShingle | Palladium-catalyzed coupling reactions practical aspects and future developments Katalyse (DE-588)4029921-1 gnd Palladiumverbindungen (DE-588)4173148-7 gnd Kupplungsreaktion (DE-588)4166199-0 gnd |
subject_GND | (DE-588)4029921-1 (DE-588)4173148-7 (DE-588)4166199-0 (DE-588)4143413-4 |
title | Palladium-catalyzed coupling reactions practical aspects and future developments |
title_auth | Palladium-catalyzed coupling reactions practical aspects and future developments |
title_exact_search | Palladium-catalyzed coupling reactions practical aspects and future developments |
title_full | Palladium-catalyzed coupling reactions practical aspects and future developments ed. by Árpád Molnár |
title_fullStr | Palladium-catalyzed coupling reactions practical aspects and future developments ed. by Árpád Molnár |
title_full_unstemmed | Palladium-catalyzed coupling reactions practical aspects and future developments ed. by Árpád Molnár |
title_short | Palladium-catalyzed coupling reactions |
title_sort | palladium catalyzed coupling reactions practical aspects and future developments |
title_sub | practical aspects and future developments |
topic | Katalyse (DE-588)4029921-1 gnd Palladiumverbindungen (DE-588)4173148-7 gnd Kupplungsreaktion (DE-588)4166199-0 gnd |
topic_facet | Katalyse Palladiumverbindungen Kupplungsreaktion Aufsatzsammlung |
url | http://deposit.dnb.de/cgi-bin/dokserv?id=4166021&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=025951028&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
work_keys_str_mv | AT molnararpad palladiumcatalyzedcouplingreactionspracticalaspectsandfuturedevelopments |