Handbook of metathesis: 1 Catalyst development and mechanism
Gespeichert in:
| Weitere Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Weinheim
Wiley-VCH
2015
|
| Ausgabe: | 2. ed. |
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XVII, 423 S. graph. Darst. |
| ISBN: | 9783527339488 |
Internformat
MARC
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| 245 | 1 | 0 | |a Handbook of metathesis |n 1 |p Catalyst development and mechanism |c ed. by Robert H. Grubbs ... |
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Datensatz im Suchindex
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|---|---|
| adam_text | CONTENTS
PREFACE XIII
LIST OF CONTRIBUTORS XV
1 HIGH-OXIDATION STATE MOLYBDENUM AND TUNGSTEN COMPLEXES RELEVANT
TO OLEFIN METATHESIS 1
RICHARD R. SCHROCK
1.1 INTRODUCTION 1
1.2 NEW IMIDO LIGANDS AND SYNTHETIC APPROACHES 2
1.3 BISPYRROLIDE AND RELATED COMPLEXES 9
1.4 MONOALKOXIDE PYRROLIDE (MAP) COMPLEXES 12
1.5 REACTIONS OF ALKYLIDENES WITH OLEFINS 14
1.6 OLEFIN AND METALLACYCLOPENTANE COMPLEXES 17
1.7 TUNGSTEN OXO COMPLEXES 21
1.8 BISARYLOXIDES 23
1.9 OTHER CONSTRUCTS 24
1.10 CONCLUSIONS 27
ACKNOWLEDGMENTS 27
REFERENCES 27
2 ALKANE METATHESIS 33
JEAN-MARIE BASSET, EMMANUEL
CALLENS, AND NASSIMA
RIACHE
2.1 INTRODUCTION 33
2.2 ALKANE METATHESIS BY SINGLE-CATALYST SYSTEMS 35
2.2.1 SUPPORTED METAL HYDRIDES 35
2.2.1.1 SUPPORTED ZR-POLYHYDRIDES 35
2.2.1.2 SUPPORTED TA-POLYHYDRIDES 36
2.2.1.3 SUPPORTED W-POLYHYDRIDES 42
2.2.2 METAL ALKYLIDENE/ALKYLIDYNE ON SURFACE OXIDE 44
2.2.2.1 STRUCTURE - ACTIVITY RELATIONSHIP OF ALKYLIDENE
COMPLEXES 44
2.2.2.2 STOICHIOMETRIC ACTIVITY OF WELL-DEFINED, METAL ALKYLIDENES WITH
ALKANES 47
2.2.2.3 SYNTHESIS OF SUPPORTED WME
6
ON SILICA 47
HTTP://D-NB.INFO/1061104818
VII
CONTENTS
2.3 ALKANE METATHESIS BY TANDEM, DUAL-CATALYTIC SYSTEMS 49
2.3.1 INTRODUCTION 49
2.3.2 THE CHEVRON PROCESS USING W0
3
/SI0
2
AND PT-LI/AL
2
0
3
49
2.3.3 TANDEM, DUAL CATALYTIC SYSTEM USING IR-PINCER LIGANDS AND
MO-ALKYLIDENE COMPLEXES 50
2.3.3.1 THE DEVELOPMENT OF ROBUST, IRIDIUM-BASED ALKANE
DEHYDROGENATION CATALYSTS 51
2.3.3.2 CYCLIC AND CROSS-ALKANE METATHESIS 62
2.4 CONCLUSION 64
REFERENCES 65
3 DIASTEREOCONTROL IN OLEFIN METATHESIS: THE DEVELOPMENT OF Z-SELECTIVE
RUTHENIUM CATALYSTS 71
BENJAMIN K. KEITZ
3.1 INTRODUCTION 71
3.2 THE CHALLENGE OF Z-SELECTIVE OLEFIN METATHESIS 71
3.3 PREVIOUS STRATEGIES 72
3.4 A SERENDIPITOUS DISCOVERY 73
3.5 CATALYST STUDIES 74
3.5.1 SUMMARY OF SUBSTITUENT EFFECTS 74
3.5.1.1 INVESTIGATING THE X-TYPE LIGAND 75
3.5.1.2 EFFECT OF THE NHC 77
3.5.2 DECOMPOSITION OF Z-SELECTIVE RU METATHESIS CATALYSTS 78
3.6 APPLICATIONS OF Z-SELECTIVE RU METATHESIS CATALYSTS 79
3.6.1 CROSS METATHESIS 79
3.6.1.1 HOMODIMERIZATION OR HOMOCOUPLING 79
3.6.1.2 OTHER CROSS-METATHESIS REACTIONS 80
3.6.2 RING-CLOSING METATHESIS (RCM) 81
3.6.3 RING-OPENING METATHESIS POLYMERIZATION (ROMP) 81
3.7 CONCLUSION 83
REFERENCES 84
4 RUTHENIUM OLEFIN METATHESIS CATALYSTS SUPPORTED BY CYCLIC ALKYL
AMINOCARBENES (CAACS) 87
DAVID S. WEINBERGER AND
VINCENT LAVAILO
4.1 INTRODUCTION 87
4.2 PROPERTIES AND PREPARATION OF CAAC LIGANDS 87
4.3 CAAC-SUPPORTED, RUTHENIUM OLEFIN METATHESIS CATALYSTS 89
4.3.1 CAAC CATALYST DEVELOPMENT AND THEIR APPLICATION TO RING-CLOSING
METATHESIS 89
4.3.2 APPLICATION TO CROSS METATHESIS, ETHENOLYSIS, AND DEGENERATE
METATHESIS 91
4.4 SUMMARY 94
REFERENCES 94
CONTENTS
I VII
5 SUPPORTED CATALYSTS AND NONTRADITIONAL REACTION MEDIA 97
DARYL P. ALLEN
5.1 INTRODUCTION 97
5.2 SUPPORTED CATALYST SYSTEMS 98
5.2.1 SUPPORTED CATALYSTS VIA COVALENT INTERACTIONS 99
5.2.1.1 GRUBBS-TYPE, RU-BASED SYSTEMS 99
5.2.1.2 SCHROCK-TYPE, MO-OR W-BASED SYSTEMS 119
5.2.2 SUPPORTED CATALYSTS VIA NON-COVALENT INTERACTIONS 126
5.2.2.1 GRUBBS-TYPE, RU-BASED SYSTEMS 126
5.2.2.2 EARLY TRANSITION-METAL SYSTEMS 136
5.3 OLEFIN METATHESIS IN NONTRADITIONAL MEDIA 136
5.3.1 OLEFIN METATHESIS IN WATER 137
5.3.1.1 MODIFIED CATALYST ARCHITECTURES 137
5.3.1.2 COMMERCIALLY AVAILABLE CATALYSTS 141
5.3.2 OLEFIN METATHESIS IN IONIC LIQUIDS 145
5.3.2.1 NEUTRAL CATALYST SYSTEMS 146
5.3.2.2 IONIC MODIFICATION TO THE CATALYST SYSTEM 147
5.3.3 OLEFIN METATHESIS IN FLUOROUS MEDIA 149
5.4 CONCLUSIONS 151
REFERENCES 152
6 INSIGHTS FROM COMPUTATIONAL STUDIES ON D METAL-CATALYZED ALKENE
AND ALKYNE METATHESIS AND RELATED REACTIONS 159
XAVIER SOLANS-MONFORT,
CHRISTOPHE
COPERET,
AND ODILE
EISENSTEIN
6.1 INTRODUCTION 159
6.2 ALKENE METATHESIS 160
6.2.1 WELL-DEFINED SYSTEMS 164
6.2.1.1 ELECTRONIC STRUCTURE OF M(ER )(=CHR
2
)(X)(Y) MOLECULAR
CATALYSTS 164
6.2.1.2 ELECTRONIC STRUCTURE OF SILICA-SUPPORTED (=SIO)M(ER
1
)(=CHTBU)(X)
CATALYSTS 167
6.2.1.3 ELECTRONIC STRUCTURE OF METALLACYCLOBUTANE INTERMEDIATES FOR THE
MOLECULAR CATALYSTS 168
6.2.1.4 ALKENE METATHESIS PATHWAY FOR WELL-DEFINED CATALYSTS 168
6.2.1.5 DEACTIVATION AND BY-PRODUCT FORMATION PATHWAYS FOR
M(ER )(=CHR
2
)(X)(Y) CATALYSTS 173
6.2.2 CLASSICAL, HETEROGENEOUS CATALYSTS 176
6.2.2.1
MO
0
3
ON ALUMINA 176
6
.2.2.2
MO0
3
ON SILICA 179
6.2.2.3 MOO
S
ON ZEOLITES 180
6.2.2.4 RE
2
0
7
ON ALUMINA AND SILICA: ALUMINA AND RELATED
ALUMINA-SUPPORTED CH
3
RE0
3
SYSTEMS 180
6.3 ALKYNE METATHESIS 182
6.3.1 GROUP 6 M(=CR)(X)(Y)
2
ALKYLIDYNE COMPLEXES IN ALKYNE
METATHESIS 184
VIIII
CONTENTS
6.3.2 NITRILE-ALKYNE CROSS METATHESIS BY THE REACTION OF W(N)X
3
WITH
2-BUTYNE 186
6.4 ALKANE METATHESIS 186
6.4.1 REACTIVITY OF TANTALUM HYDRIDES 187
6.4.2 REACTIVITY OF THE ALUMINA-SUPPORTED, BISALKYL ALKYLIDYNE TUNGSTEN
CATALYSTS 189
6.5 OUTLOOK 191
REFERENCES 192
7 COMPUTATIONAL STUDIES OF RUTHENIUM-CATALYZED OLEFIN
METATHESIS 199
PENG LIU, BUCK L H. TAYLOR,
JESUS
GARCIA-LOPEZ,
AND KENDALL N. HOUK
7.1 INTRODUCTION 199
7.2 COMPUTATIONAL INVESTIGATIONS OF NON-CHELATED RUTHENIUM
CATALYSTS 200
7.2.1 REACTION MECHANISMS 200
7.2.1.1 GENERAL MECHANISM 200
7.2.1.2 ASSOCIATIVE AND DISSOCIATIVE MECHANISMS FOR INITIATION 201
7.2.1.3 INITIATION OF CATALYSTS WITH HEMILABILE LIGANDS 202
7.2.1.4 BOTTOM-BOUND AND SIDE-BOUND OLEFIN COMPLEXES 203
7.2.1.5 STRUCTURE OF THE METALLACYCLOBUTANE 206
7.2.2 EFFECTS OF SPECTATOR LIGANDS 208
7.2.2.1 STABILITY OF THE METALLACYCLOBUTANE 209
7.2.2.2 BINDING OF PHOSPHINE AND OLEFIN LIGANDS 210
7.2.2.3 ROTAMERIC EFFECTS ON THE ALKYLIDENE 211
7.2.2.4 EFFECT OF ANIONIC LIGANDS 215
7.2.2.5 SUMMARY OF LIGAND EFFECTS 216
7.2.3 E/Z SELECTIVITY 216
7.2.4 REACTIVITIES OF SUBSTITUTED OLEFINS 219
7.2.5 COMPUTATIONS ON DIFFERENT TYPES OF OLEFIN METATHESIS
REACTIONS 221
7.2.5.1 RING-OPENING METATHESIS POLYMERIZATION 223
7.2.5.2 RING-CLOSING METATHESIS 225
7.2.5.3 ENYNE METATHESIS 227
7.2.6 DECOMPOSITION OF RUTHENIUM OLEFIN METATHESIS
CATALYSTS 229
7.2.7 ALKENE ISOMERIZATION 232
7.3 COMPUTATIONAL INVESTIGATIONS OF CHELATED, Z-SELECTIVE RUTHENIUM
CATALYSTS 236
7.3.1 MECHANISM AND ORIGINS OF Z SELECTIVITY 238
7.3.2 DECOMPOSITION PATHWAYS OF THE CHELATED RUTHENIUM
CATALYSTS 244
7.4 ACCURACY OF THE COMPUTATIONAL METHODS 247
REFERENCES 249
CONTENTS
IX
8 INTERMEDIATES IN OLEFIN METATHESIS 253
ANNA G. WENZEL
8.1 INTRODUCTION 253
8.2 METATHESIS-ACTIVE, EARLY-METAL METALLACYCLES 253
8.3 INTERMEDIATES IN RUTHENIUM-CATALYZED OLEFIN METATHESIS 258
8.3.1 RUTHENACYCLOBUTANE INTERMEDIATES DERIVED FROM PHOSPHONIUM
ALKYLIDENE COMPLEXES 260
8.3.2 RUTHENACYCLOBUTANE INTERMEDIATES DERIVED FROM BISPYRIDYL
COMPLEXES 267
8.3.3 RUTHENIUM ALKYLIDENE/OLEFIN INTERMEDIATES 268
8.4 FUTURE DIRECTIONS 269
REFERENCES 269
9 FACTORS AFFECTING INITIATION RATES 273
JUSTIN R. GRIFFITHS AND
STEVEN T. DIVER
9.1 INTRODUCTION 273
9.1.1 DISCUSSION OF GENERAL TERMS 273
9.1.2 EXPERIMENTAL MEASUREMENT OF INITIATION RATES 274
9.2 GRUBBS SECOND-GENERATION CATALYST 276
9.2.1 PHOSPHINE DISSOCIATION RELATED TO INITIATION AND METATHESIS
EFFICIENCY 276
9.2.2 HALIDE SUBSTITUTION 279
9.2.3 SOLVENT EFFECTS 280
9.2.4 EFFECT OF ALKENE STRUCTURE 281
9.3 GRUBBS-HOVEYDA-TYPE PRECATALYSTS 281
9.4 PYRIDINE SOLVATES 289
9.5 PIERS CATALYSTS 290
9.6 INDENYLIDENE CARBENE PRECATALYSTS 293
9.7 Z-SELECTIVE CATALYSTS 296
9.8 HERRMANN-TYPE, BISNHCS 298
9.9 CONCLUSIONS 299
ACKNOWLEDGMENTS 302
REFERENCES 302
10 DEGENERATE METATHESIS 305
IAN C. STEWART
10.1 INTRODUCTION 305
10.2 DEGENERATE METATHESIS MECHANISMS 305
10.2.1 POTENTIAL IMPACT ON CATALYST EFFICIENCIES 306
10.3 DEGENERATE METATHESIS WITH EARLY TRANSITION-METAL CATALYSTS 307
10.3.1 HOMOGENEOUS, EARLY TRANSITION-METAL CATALYSTS 307
10.3.2 HETEROGENEOUS, EARLY TRANSITION-METAL CATALYSTS 310
10.3.3 CONCLUSIONS ON DEGENERATE METATHESIS WITH EARLY TRANSITION-METAL
CATALYSTS 314
10.4 DEGENERATE METATHESIS WITH RUTHENIUM CATALYSTS 315
X |
CONTENTS
10.5 BENEFICIAL EFFECTS OF DEGENERATE METATHESIS 318
10.6 CONCLUSIONS 321
REFERENCES 321
11 MECHANISMS OF OLEFIN METATHESIS CATALYST DECOMPOSITION AND
METHODS OF CATALYST REACTIVATION 323
YANN SCHRODI
11.1 INTRODUCTION 323
11.2 DECOMPOSITION OF MO AND W IMIDO ALKYLIDENE CATALYSTS AND RELATED
COMPLEXES 324
11.2.1 MECHANISMS OF DECOMPOSITION OF MO AND W SYSTEMS 324
11.2.2 STRATEGIES TO EXTEND THE LIFETIME OF MO AND W CATALYSTS 327
11.3 DECOMPOSITION OF RU ALKYLIDENE CATALYSTS AND RELATED
COMPLEXES 328
11.3.1 THERMAL DECOMPOSITION OF FIRST-GENERATION SYSTEMS 328
11.3.2 THERMAL DECOMPOSITION OF SECOND-GENERATION SYSTEMS 333
11.3.3 DECOMPOSITION IN THE PRESENCE OF SMALL MOLECULES AND FUNCTIONAL
GROUPS 335
11.3.4 STRATEGIES TO PREVENT THE DECOMPOSITION OF RU CATALYSTS 337
11.3.5 REACTIVATION OF RUTHENIUM CATALYSTS 338
11.4 CONCLUSIONS 339
REFERENCES 340
12 SOLVENT AND ADDITIVE EFFECTS ON OLEFIN METATHESIS 343
SHAWN K. COLLINS
12.1 GENERAL INTRODUCTION 343
12.2 SOLVENT EFFECTS ON OLEFIN METATHESIS 344
12.3 ADDITIVE EFFECTS IN OLEFIN METATHESIS 354
12.4 SUMMARY 374
REFERENCES 375
13 METATHESIS PRODUCT PURIFICATION 379
DAVID W. KNIGHT
13.1 INTRODUCTION 379
13.2 CHROMATOGRAPHIC AND CHEMICAL REMOVAL OF RUTHENIUM 380
13.3 REMOVAL BY COMPLEXATION 381
13.4 CONCLUSION 386
REFERENCES 386
14 RUTHENIUM INDENYLIDENE CATALYSTS FOR ALKENE METATHESIS 389
PIERRE H. DIXNEUFAND CHRISTIAN BRUNEAU
14.1 INTRODUCTION 389
14.2 THE INITIAL DEVELOPMENT OF INDENYLIDENE METAL COMPLEXES FOR
ALKENE METATHESIS 390
14.2.1 THE RUTHENIUM ALLENYLIDENE PRECURSORS 390
CONTENTS | XI
14.2.2 FROM ALLENYLIDENE TO INDENYLIDENE RUTHENIUM COMPLEXES
AND CATALYSTS 391
14.2.3 INTRAMOLECULAR ALLENYLIDENE-INTO-INDENYLIDENE
REARRANGEMENTS 393
14.3 BINUCLEAR INDENYLIDENE RUTHENIUM CATALYSTS ARISING FROM
RUTHENIUM(ARENE) COMPLEXES 394
14.4 PREPARATION OF RUTHENIUM INDENYLIDENE CATALYSTS FROM
RUCL
2
(PPH
3
)
3
396
14.4.1 FIRST-GENERATION RUTHENIUM INDENYLIDENE CATALYSTS BEARING TWO
PHOSPHINE LIGANDS 396
14.4.2 FIRST-GENERATION RUTHENIUM INDENYLIDENE CATALYSTS BEARING A
CHELATING LIGAND 399
14.4.2.1 FIRST-GENERATION RUTHENIUM INDENYLIDENE CATALYSTS BEARING A
BIDENTATE SCHIFF BASE LIGAND 399
14.4.2.2 FIRST-GENERATION RUTHENIUM INDENYLIDENE CATALYSTS BEARING A
BIDENTATE DICHALCOGENOIMIDODIPHOSPHINATE LIGAND 400
14.4.3 SECOND-GENERATION RUTHENIUM INDENYLIDENE CATALYSTS BEARING A
N-HETEROCYCLIC CARBENE OR A CHELATING NHC-PHOSPHINE
LIGAND 400
14.4.4 SECOND-GENERATION RUTHENIUM INDENYLIDENE CATALYSTS BEARING A
N-HETEROCYCLIC CARBENE LIGAND AND A PHOSPHITE LIGAND 403
14.4.4.1 THIRD-GENERATION RUTHENIUM INDENYLIDENE CATALYSTS BEARING AT
LEAST
ONE PYRIDINE LIGAND 404
14.5 RUTHENIUM CATALYSTS BEARING A CHELATING INDENYLIDENE LIGAND 406
14.6 CONCLUSION 411
REFERENCES 412
INDEX 417
|
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| id | DE-604.BV042407305 |
| illustrated | Illustrated |
| indexdate | 2024-07-10T01:20:41Z |
| institution | BVB |
| isbn | 9783527339488 |
| language | English |
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| publishDate | 2015 |
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| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Handbook of metathesis 1 Catalyst development and mechanism ed. by Robert H. Grubbs ... 2. ed. Weinheim Wiley-VCH 2015 XVII, 423 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Metathese Chemie (DE-588)4169656-6 gnd rswk-swf Metathese Chemie (DE-588)4169656-6 s DE-604 Grubbs, Robert H. 1942-2021 (DE-588)124993532 edt (DE-604)BV025307693 1 Erscheint auch als Online-Ausgabe, EPUB 978-3-527-69399-3 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-69401-3 Erscheint auch als Online-Ausgabe, PDF 978-3-527-69400-6 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027842877&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Handbook of metathesis Metathese Chemie (DE-588)4169656-6 gnd |
| subject_GND | (DE-588)4169656-6 |
| title | Handbook of metathesis |
| title_auth | Handbook of metathesis |
| title_exact_search | Handbook of metathesis |
| title_full | Handbook of metathesis 1 Catalyst development and mechanism ed. by Robert H. Grubbs ... |
| title_fullStr | Handbook of metathesis 1 Catalyst development and mechanism ed. by Robert H. Grubbs ... |
| title_full_unstemmed | Handbook of metathesis 1 Catalyst development and mechanism ed. by Robert H. Grubbs ... |
| title_short | Handbook of metathesis |
| title_sort | handbook of metathesis catalyst development and mechanism |
| topic | Metathese Chemie (DE-588)4169656-6 gnd |
| topic_facet | Metathese Chemie |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027842877&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| volume_link | (DE-604)BV025307693 |
| work_keys_str_mv | AT grubbsroberth handbookofmetathesis1 |