N-heterocyclic carbenes: effective tools for organometallic synthesis
Saved in:
| Other Authors: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Weinheim
Wiley-VCH
2014
|
| Subjects: | |
| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Physical Description: | XXII, 543 S. graph. Darst. |
| ISBN: | 3527334904 9783527334902 9783527671229 |
Staff View
MARC
| LEADER | 00000nam a2200000 c 4500 | ||
|---|---|---|---|
| 001 | BV041991339 | ||
| 003 | DE-604 | ||
| 005 | 20160427 | ||
| 007 | t | ||
| 008 | 140724s2014 gw d||| |||| 00||| eng d | ||
| 015 | |a 14,N15 |2 dnb | ||
| 016 | 7 | |a 1049503341 |2 DE-101 | |
| 020 | |a 3527334904 |9 3-527-33490-4 | ||
| 020 | |a 9783527334902 |c Gb. : ca. EUR 149.00 (DE) (freier Pr.), ca. EUR 153.20 (AT) (freier Pr.), ca. sfr 201.00 (freier Pr.) |9 978-3-527-33490-2 | ||
| 020 | |a 9783527671229 |c oBook |9 978-3-527-67122-9 | ||
| 024 | 3 | |a 9783527334902 | |
| 028 | 5 | 2 | |a Best.-Nr.: 1133490 000 |
| 035 | |a (OCoLC)876382512 | ||
| 035 | |a (DE-599)DNB1049503341 | ||
| 040 | |a DE-604 |b ger |e rakddb | ||
| 041 | 0 | |a eng | |
| 044 | |a gw |c XA-DE-BW | ||
| 049 | |a DE-20 |a DE-11 |a DE-355 |a DE-29T |a DE-19 | ||
| 082 | 0 | |a 547.593044242 |2 22/ger | |
| 084 | |a VK 5500 |0 (DE-625)147401:253 |2 rvk | ||
| 084 | |a VK 7200 |0 (DE-625)147417:253 |2 rvk | ||
| 084 | |a 540 |2 sdnb | ||
| 245 | 1 | 0 | |a N-heterocyclic carbenes |b effective tools for organometallic synthesis |c ed. by Steven P. Nolan |
| 263 | |a 201409 | ||
| 264 | 1 | |a Weinheim |b Wiley-VCH |c 2014 | |
| 300 | |a XXII, 543 S. |b graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 0 | 7 | |a Heterocyclische Verbindungen |0 (DE-588)4159726-6 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Carbene |0 (DE-588)4147281-0 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Metallorganische Chemie |0 (DE-588)4602390-2 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Stickstoffheterocyclen |0 (DE-588)4183269-3 |2 gnd |9 rswk-swf |
| 655 | 7 | |0 (DE-588)4143413-4 |a Aufsatzsammlung |2 gnd-content | |
| 689 | 0 | 0 | |a Carbene |0 (DE-588)4147281-0 |D s |
| 689 | 0 | 1 | |a Stickstoffheterocyclen |0 (DE-588)4183269-3 |D s |
| 689 | 0 | 2 | |a Metallorganische Chemie |0 (DE-588)4602390-2 |D s |
| 689 | 0 | |5 DE-604 | |
| 689 | 1 | 0 | |a Heterocyclische Verbindungen |0 (DE-588)4159726-6 |D s |
| 689 | 1 | 1 | |a Carbene |0 (DE-588)4147281-0 |D s |
| 689 | 1 | |8 1\p |5 DE-604 | |
| 700 | 1 | |a Nolan, Steven P. |d 1962- |0 (DE-588)132074303 |4 edt | |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, EPUB |z 978-3-527-67124-3 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, MOBI |z 978-3-527-67123-6 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, PDF |z 978-3-527-67125-0 |
| 856 | 4 | 2 | |m X:MVB |q text/html |u http://deposit.dnb.de/cgi-bin/dokserv?id=4624829&prov=M&dok_var=1&dok_ext=htm |3 Inhaltstext |
| 856 | 4 | 2 | |m DNB Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027433576&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 883 | 1 | |8 1\p |a cgwrk |d 20201028 |q DE-101 |u https://d-nb.info/provenance/plan#cgwrk | |
| 943 | 1 | |a oai:aleph.bib-bvb.de:BVB01-027433576 | |
Record in the Search Index
| _version_ | 1806328611119038464 |
|---|---|
| adam_text |
CONTENTS
LIST OF CONTRIBUTORS
XVII
PREFACE
XXI
1 ^-HETEROCYCLIC CARBENES 1
DAVID J. NELSON
AND STEVEN P. NOLAN
1.1 INTRODUCTION I
1.2 STRUCTURE AND PROPERTIES OF NHCS 1
1.3 ABNORMAL CARBENES 5
1.4 - WHY ARE NHCS STABLE?
6
1.5 BONDING OF NHCS TO METAL CENTERS
8
1.6 QUANTIFYING THE PROPERTIES OF NHCS 13
1.6.1 STERIC IMPACT 13
1.6.2 ELECTRONIC PROPERTIES 14
1.7 ^-HETEROCYCLIC CARBENES IN THE CONTEXT OF OTHER STABLE CARBENES 16
1.8 SYNTHESIS OF NHCS 19
1.9 SALTS AND ADDUCTS OF NHCS 20
1.10 SUMMARY 22
REFERENCES 22
2 TUNING AND QUANTIFYING STERIC AND ELECTRONIC EFFECTS OF
N-HETEROCYDIC CARBENES
25
LAURA FALIVENE, ALBERT
POATER, AND LUIGI CAVALLO
2.1 INTRODUCTION 25
2.2 STERIC EFFECTS IN NHC LIGANDS 26
2.3 ELECTRONIC EFFECTS IN NHC LIGANDS 31
2.4 CONCLUSIONS 35
REFERENCES 35
3 CHIRAL MONODENDATE N-HETEROCYCLIC CARBENE LIGANDS IN ASYMMETRIC
CATALYSIS
39
LINGLIN WU, ALVARO SALVADOR, AND RETO DORTA
3.1 INTRODUCTION 39
HTTP://D-NB.INFO/1049503341
VIII
| CONTENTS
3.2 NHC-RU 40
3.2.1 ASYMMETRIC METATHESIS 40
3.2.2 ASYMMETRIC HYDROGENATION 44
3.2.3 ASYMMETRIC HYDROSILYLATION 47
3.3 NHC-RH 48
3.3.1 ASYMMETRIC CATALYSIS USING BORONIC ACIDS AS
NUCLEOPHILES 48
3.3.2 ASYMMETRIC HYDROSILYLATION SO
3.3.3 ASYMMETRIC HYDROFORMYLATION 53
3.4 NHC-IR S3
3.5 NHC-NI 55
3.6 NHC-PD 56
3.6.1 ASYMMETRIC INTRAMOLECULAR A-ARYLATION OF
AMIDES 56
3.6.2 ASYMMETRIC DIAMINATION 62
3.6.3 OTHER ASYMMETRIC CATALYSIS USING NHC-PD 63
3.7 NHC-CU 65
3.7.1 ASYMMETRIC CONJUGATE ADDITION 65
3.7.2 ASYMMETRIC ALLYLIC SUBSTITUTION 67
3.7.3 SILYL CONJUGATE ADDITION 69
3.7.4 ENANTIOSELECTIVE P-BORATION 70
3.7.5 ASYMMETRIC HYDROSILYLATION 72
3.7.6 ASYMMETRIC ADDITION TOI IMINES 73
3.8 NHC-AG 75
3.9 NHC-AU 75
3.9.1 ENANTIOSELECTIVE CYCLOISOMERIZATIONS 76
3.9.2 ENANTIOSELECTIVE HYDROGENATION 78
3.9.3 ENANTIOSELECTIVE CYCLOADDITION 79
3.10 CONCLUSION 79
REFERENCES 80
4 (A/-HETEROCYCLIC CARBENE)-PALLADIUM COMPLEXES
IN CATALYSIS
85
MARIO HOYOS, DANIEL GUEST, AND OSCAR
NAVARRO
4.1 INTRODUCTION 85
4.2 CROSS-COUPLING REACTIONS 85
4.2.1 SUZUKI-MIYAURA COUPLING 85
4.2.2 BUCHWALD-HARTWIG AMINATIONS 88
4.2.3 NEGISHI REACTIONS 89
4.2.4 HIYAMA COUPLING 89
4.2.5 KUMADA COUPLING 90
4.2.6 SONOGASHIRA COUPLING 90
4.2.7 HECK REACTION 92
4.3 CHELATES AND PINCER LIGANDS 93
4.4 ASYMMETRIC CATALYSIS 97
CONTENTS
IIX
4.5 OXIDATION REACTIONS 100
4.6 TELOMERIZATION, OLIGOMERIZATION AND POLYMERIZATION 102
4.7 ANTICANCER NHC-PD COMPLEXES 107
REFERENCES 107
5 NHC PLATINUM(O) COMPLEXES: UNIQUE CATALYSTS FOR THE
HYDROSILYLATION OF ALKENES AND ALKYNES
111
STEVE DIERICK
AND ISTVAN E. MARKO
5.1 INTRODUCTION 111
5.2 HYDROSILYLATION OF ALKENES: THE BEGINNING 112
5.3 INITIAL RESULTS WITH PHOSPHINE LIGANDS 114
5.4 NHC PLATINUM(O) COMPLEXES: THE BREAKTHROUGH 115
5.4.1 SYNTHESIS OF NHC PLATINUM(O) COMPLEXES AND KINETIC ASSAYS 115
5.4.2 FUNCTIONAL GROUP TOLERANCE AND SUBSTRATE SCOPE 120
5.4.3 MECHANISTIC STUDIES 122
5.4.3.1 ACTIVATION PERIOD 123
5.4.3.2 CATALYST DEACTIVATION PATHWAYS 125
5.4.3.3 SEMIQUANTITATIVE KINETIC STUDIES 127
5.4.3.4 QUANTITATIVE KINETIC MODELING 129
5.4.3.5 CONCLUSIONS 133
5.5 HYDROSILYLATION OF ALKYNES 133
5.5.1 CATALYST SCREENING AND THE IMPACT OF NHCS ON REGIOSELECTIVITY 134
5.5.2 INFLUENCE OF SILANE ON REGIOSELECTIVITY 137
5.5.3 SECOND-GENERATION CATALYST FOR THE HYDROSILYLATION OF ALKYNES 138
5.5.4 FUNCTIONAL GROUP TOLERANCE AND SUBSTRATE SCOPE 139
5.5.5 MECHANISTIC STUDIES 142
5.5.5.1 QUALITATIVE KINETIC STUDIES 142
5.5.5.2 CATALYST ACTIVATION AND DEACTIVATION PATHWAYS 143
5.5.5.3 PROPOSED MECHANISM 145
5.6 CONCLUSIONS 146
REFERENCES 146
6 SYNTHESIS AND MEDICINAL PROPERTIES OF SILVER-NHC COMPLEXES AND
IMIDAZOLIUM SALTS
151
PATRICK O. WAGERS, KERRI
L SHELTON, MATTHEW J. PANZNER, CLAIRE A. TESSIER,
AND WILEY J. YOUNGS
6.1 INTRODUCTION 151
6.2 SILVER-NHC COMPLEXES AS ANTIMICROBIAL AGENTS 152
6.3 SILVER-NHC COMPLEXES AS ANTICANCER AGENTS 163
6.4 CONCLUSIONS 170
REFERENCES 171
7 MEDICAL APPLICATIONS OF NHC-GOLD AND-COPPER COMPLEXES
173
FA'FMA
LAZREG AND CATHERINE S. J. CAZIN
7.1 INTRODUCTION 173
7.2 GOLD ANTIMICROBIAL AGENTS 173
X| CONTENTS
7.3 METALS AS ANTITUMOR REAGENTS 178
7.4 COPPER COMPLEXES AS ANTITUMORAL REAGENTS 195
7.5 CONCLUSION 196
REFERENCES 197
8 NHC-COPPER COMPLEXES AND THEIR APPLICATIONS
199
FA'IMA LAZREG
AND CATHERINE S. J. CAZIN
8.1 INTRODUCTION 199
8.2 HISTORY OF NHC-COPPER SYSTEMS 199
8.3 HYDROSILYLATION 200
8.4 ALLENE FORMATION 202
8.5 1,4-REDUCTION 205
8.6 CONJUGATE ADDITION 206
8.6.1 ZINC REAGENTS 206
8.6.2 GRIGNARD REAGENTS 207
8.6.3 ALUMINUM REAGENTS 209
8.6.4 BORON REAGENTS 209
8.7 HYDROTHIOLATION, HYDROALKOXYLATION,
HYDROAMINATION 210
8.8 CARBOXYLATION AND CARBONYLATION (VIA BORONIC ACIDS,
CH ACTIVATION): CO2 INSERTION 213
8.9 [3 + 2} CYCLOADDITION REACTION: FORMATION OF
TRIAZOLE 215
8.10 ALLYLIC SUBSTITUTION 217
8.10.1 ZINC REAGENTS 217
8.10.2 GRIGNARD REAGENTS 217
8.10.3 ALUMINUM REAGENTS 219
8.10.4 BORON REAGENTS 220
8.11 CARBENE AND NITRENE TRANSFER 221
8.12 BORATION REACTION 222
8.12.1 BORATION OF KETONE AND ALDEHYDE 222
8.12.2 BORATION OF ALKENE 223
8.12.3 BORATION OF ALKYNE 224
8.12.4 CARBOBORATION 226
8.13 OLEFINATION OF CARBONYL DERIVATIVES 226
8.14 COPPER-MEDIATED CROSS-COUPLING REACTION 228
8.15 FLUORIDE CHEMISTRY 230
8.16 OTHER REACTIONS 231
8.16.1 A
3
COUPLING 231
8.16.2 SEMIHYDROGENATION OF ALKYNE 232
8.16.3 BOROCARBOXYLATION OF ALKYNE 233
8.16.4 HYDROCARBOXYLATION OF ALKYNE 234
8.17 TRANSMETALATION 235
8.18 CONCLUSION 237
REFERENCES 237
CONTENTS
9
NHC-AU(L) COMPLEXES: SYNTHESIS, ACTIVATION, AND APPLICATION
243
THOMAS WURM, ABDULLAH MOHAMED ASIRI, AND A. STEPHEN K. HASHMI
9.1 INTRODUCTION 243
9.2 SYNTHESIS OF NHC-GOLD(I) CHLORIDES 244
9.3 ACTIVATION OF NHC-AU(I) CHLORIDES 248
9.4 APPLICATIONS OF NHC-AU(I) CATALYSTS 253
9.4.1 IMPROVEMENT OF CATALYST STABILITY DURING GOLD-CATALYZED REACTIONS
DUE TO THE USE OF NHC LIGANDS 253
9.4.2 IMPROVEMENT OF GOLD CATALYSIS DUE TO TUNING THE STERIC
PROPERTIES OF THE NHC LIGANDS USED 256
9.4.3 IMPROVEMENT OF GOLD CATALYSIS BY TUNING THE ELECTRONIC
PROPERTIES OF THE NHC LIGANDS USED 257
9.4.4 ALTERATION OF THE REACTIVITY OF GOLD CATALYSIS BY SWITCHING
FROM PHOSPHINE TO NHC LIGANDS 258
9.4.5 ENANTIOSELECTIVE GOLD CATALYZED TRANSFORMATIONS BASED ON CHIRAL,
ENANTIOPURE NHC-BASED CATALYSTS 264
9.5 CONCLUSION 266
REFERENCES 267
10 RECENT DEVELOPMENTS IN THE SYNTHESIS AND APPLICATIONS
OF RHODIUM AND IRIDIUM COMPLEXES BEARING N-HETEROCYCLIC
CARBENE LIGANDS
271
MACARENA POYATOS, GREGORIO GUISADO-BARRIOS, AND EDUARDO
PERIS
10.1 INTRODUCTION 271
10.2 RH- AND IR-NHC-BASED COMPLEXES: STRUCTURAL AND ELECTRONIC
FEATURES 271
10.2.1 MONO-NHCS 271
10.2.2 CHELATING NHCS 273
10.2.2.1 BIDENTATE CHELATING BIS-NHC COMPLEXES 273
10.2.2.2 CHELATING CHIRAL BIS-NHC COMPLEXES 279
10.2.2.3 DONOR-FUNCTIONALIZED CHELATING NHC COMPLEXES 280
10.2.3 BRIDGING NHCS 282
10.2.3.1 COMPLEXES WITH NHC LIGANDS WITH FACIALLY OPPOSED COORDINATION
ABILITIES 285
10.3 CATALYTIC APPLICATIONS OF RHODIUM AND IRIDIUM NHC-BASED
COMPLEXES 288
10.3.1 REDUCTIONS 288
10.3.1.1 TRANSFER HYDROGENATION 288
10.3.1.2 REDUCTIONS WITH H
2
290
10.3.1.3 BORROWING-HYDROGEN PROCESSES 292
10.3.1.4 HYDROSILYLATION 292
10.3.2 ARYLATION AND BORYLATION REACTIONS WITH ORGANOBORON REAGENTS 293
10.3.3 OXIDATIONS 295
10.3.3.1 DEHYDROGENATION OF ALCOHOLS 295
10.3.3.2 DEHYDROGENATION OF ALKANES 295
XII
| CONTENTS
10.3.3.3 WATER OXIDATION 296
10.3.4 OTHER IMPORTANT CATALYTIC PROCESSES 296
10.3.4.1 H/D EXCHANGE REACTIONS 296
10.3.4.2 DEHYDROGENATION OF SATURATED CC AND BN BONDS 296
10.3.4.3 HYDROTHIOLATION OF ALKYNES 297
10.3.4.4 CIS-SELECTED CYCLOPROPANATION REACTIONS 298
10.3.4.5 HYDROAMINATION OF ALKYNES 298
10.3.4.6 MAGNETIZATION TRANSFER FROM PARA-HYDROGEN 298
10.4 ABBREVIATIONS 298
REFERENCES 299
11 N-HETEROCYDIC CARBENE-RUTHENIUM COMPLEXES: A PROMINENT
BREAKTHROUGH IN METATHESIS REACTIONS
307
SUDHEENDRAN MAVILA AND N. GABRIEL LEMCOFF
11.1 INTRODUCTION 307
11.2 VARIATIONS OF NHC IN RUTHENIUM COMPLEXES 313
11.3 MODIFICATIONS IN IMIDAZOL- AND IMIDAZOLIN-2-YLIDENE
LIGANDS 313
11.4 INFLUENCE OF SYMMETRICALLY 1,3-SUBSTITUTED //-HETEROCYCLIC
CARBENE IN METATHESIS 313
11.4.1 N, AT-DIALKYL SUBSTITUTED N-HETEROCYCLIC CARBENE COMPLEXES 313
11.4.2 N, JV-DIARYL SUBSTITUTED IV-HETEROCYCLIC CARBENE COMPLEXES 314
11.5 UNSYMMETRICALLY AW-SUBSTITUTED N-HETEROCYCLIC CARBENES 319
11.5.1 JV-ALKYL-W-ARYL SUBSTITUTED N-HETEROCYCLIC
CARBENE COMPLEXES 319
11.5.2 N, AT-DIARYL-SUBSTITUTED AF-HETEROCYCLIC CARBENE COMPLEXES 323
11.5.3 INFLUENCE OF 4,5-SUBSTITUTED N-HETEROCYCLIC CARBENES IN
METATHESIS 325
11.5.4 FOUR-, SIX-, AND SEVEN-MEMBERED N-HETEROCYCLIC CARBENES 327
11.5.5 HETEROATOM CONTAINING N-HETEROCYCLIC CARBENES 328
11.5.6 AF-HETEROCYCLIC CARBENE BEARING CHIRAL RU COMPLEXES 330
11.5.7 CHIRAL MONODENTATE AF-HETEROCYCLIC CARBENES 330
11.5.8 CHIRAL BIDENTATE N-HETEROCYCLIC CARBENES 334
11.5.9 NHCS FOR METATHESIS IN WATER AND PROTIC SOLVENTS 335
REFERENCES 337
12 RUTHENIUM /V-HETEROCYDIC CARBENE COMPLEXES FOR THE CATALYSIS
OF NONMETATHESIS ORGANIC TRANSFORMATIONS
341
LEONID SCHWARTSBURD AND
MICHAEL K. WHITTLESEY
12.1 INTRODUCTION 341
12.2 TRANSFER HYDROGENATION 341
12.3 DIRECT HYDROGENATION (AND HYDROSILYLATION) 346
12.4 BORROWING HYDROGEN 351
12.5 ALCOHOL RACEMIZATION 356
12.6 ARYLATION 357
12.7 REACTIONS OF ALKYNES 359
12.8 ISOMERIZATION OF C=C BONDS 360
12.9 ALLYLIC SUBSTITUTION REACTIONS 361
12.10 MISCELLANEOUS REACTIONS 363
12.11 CONCLUSIONS 365
REFERENCES 365
13 NICKEL COMPLEXES OF AF-HETEROCYDIC CARBENES
371
M. TAYLOR HAYNES
II,
EVAN P. JACKSON, AND JOHN
MONTGOMERY
13.1 INTRODUCTION 371
13.2 NICKEL-NHC CATALYSTS 372
13.2.1 IN SITU METHODS TO GENERATE NI-NHC COMPLEXES 372
13.2.2 DISCRETE NI(0)-NHC CATALYSTS 373
13.2.2.1 CATALYSTS DERIVED FROM NICKEL(O) AND NICKEL(II)
SOURCES 373
13.2.2.2 NICKEL(0)-NHC COMPLEXES STABILIZED BY JI SYSTEMS 373
13.2.3 DISCRETE NI(I)-NHC CATALYSTS 374
13.2.4 DISCRETE NI(II)-NHC CATALYSTS 374
13.3 CROSS-COUPLING REACTIONS 376
13.3.1 CARBON-CARBON BOND FORMING REACTIONS 376
13.3.1.1 KUMADA-CORRIU COUPLING REACTION 376
13.3.1.2 SUZUKI-MIYAURA COUPLING REACTION 378
13.3.1.3 NEGISHI COUPLING REACTION 381
13.3.1.4 HECK REACTION 381
13.3.2 CARBON-HETEROATOM BOND-FORMING REACTIONS 382
13.3.2.1 CARBON-NITROGEN BOND-FORMING REACTIONS 382
13.3.2.2 CARBON-SULFUR BOND-FORMING REACTIONS 382
13.4 OXIDATION/REDUCTION REACTIONS 383
13.4.1 DEHALOGENATION 383
13.4.2 IMINE REDUCTION 383
13.4.3 ALCOHOL OXIDATION 384
13.4.4 ARYL ETHER REDUCTION 384
13.5 HYDROSILYLATION 385
13.5.1 HYDROSILYLATION OF ALKYNES 385
13.5.2 HYDROSILYLATION OF CARBONYLS 385
13.6 CYCLOADDITIONS 386
13.6.1 [2+2+2] CYCLOADDITION 386
13.6.1.1 DIYNES AND CARBON DIOXIDE 386
13.6.1.2 DIYNES AND ALDEHYDES 387
13.6.1.3 ENYNES AND ALDEHYDES/KETONES 387
13.6.1.4 HETEROCYCLES FROM [2+2+2] CYCLOADDITIONS 387
13.6.1.5 CARBOCYCLES FROM ARYNE INTERMEDIATES 388
13.6.2 [3+2] CYCLOADDITION 388
13.6.3 [4+2+2] CYCLOADDITION 389
13.7 ISOMERIZATION 390
CONTENTS
13.8 REDUCTIVE COUPLING 390
13.8.1 ALDEHYDES AND DIENES 390
13.8.2 ALDEHYDES AND ALKYNES 391
13.8.3 ALDEHYDES AND ALLENES 392
13.8.4 ALDEHYDES AND NORBORNENE 393
13.9 CONCLUSIONS AND OUTLOOK 393
REFERENCES 394
14 COORDINATION CHEMISTRY, REACTIVITY, AND APPLICATIONS
OF EARLY TRANSITION METAL COMPLEXES BEARING /V-HETEROCYDIC
CARBENE LIGANDS
397
STFYHANE BELLEMIN-LAPONNAZ AND SAMUEL DAGORNE
14.1 INTRODUCTION 397
14.2 GROUP 3 METAL COMPLEXES 398
14.3 GROUP 4 METAL COMPLEXES 402
14.4 GROUP 5 METAL COMPLEXES 411
14.5 GROUP 6 METAL COMPLEXES 413
14.6 GROUP 7 METAL COMPLEXES 418
14.7 CONCLUSION 421
REFERENCES 422
15 NHC COMPLEXES OF MAIN GROUP ELEMENTS: NOVEL STRUCTURES,
REACTIVITY, AND CATALYTIC BEHAVIOR
427
LUKE J. MURPHY, KATHERINE
N. ROBERTSON, JASON
D. MASUDA, AND
JASON A. C. CLYBURNE
15.1 INTRODUCTION 427
15.2 STRUCTURES OF COMMON NHCS FOR MAIN GROUP CHEMISTRY
15.3 NHC COMPLEXES OF GROUP 1 ELEMENTS 429
15.3.1 LITHIUM 429
15.3.2 SODIUM 432
15.3.3 POTASSIUM 433
15.4 NHC COMPLEXES OF GROUP 2 ELEMENTS 434
15.4.1 BERYLLIUM 434
15.4.2 MAGNESIUM 436
15.4.3 CALCIUM, STRONTIUM, AND BARIUM 437
15.5 NHC COMPLEXES OF GROUP 13 ELEMENTS 438
15.5.1 BORON 438
15.5.1.1 CHEMISTRY OF NHCS WITH BORANES 439
15.5.1.2 NHC-BORANES AS HYDROGEN SOURCES 441
15.5.1.3 FRUSTRATED LEWIS PAIRS 444
15.5.1.4 CHEMISTRY OF NHCS AND CHARGED BORON COMPOUNDS 446
15.5.1.5 NHC CHEMISTRY OF OTHER BORON COMPOUNDS 448
15.5.2 ALUMINUM 452
15.5.3 GALLIUM 454
15.5.4 INDIUM AND THALLIUM 456
CONTENTS |XV
15.6 NHC COMPLEXES OF GROUP 14 ELEMENTS 456
15.6.1 CARBON 456
15.6.2 SILICON 459
15.6.3 GERMANIUM 464
15.6.4 TIN AND LEAD 466
15.7 NHC COMPLEXES OF GROUP 15 ELEMENTS 467
15.7.1 NITROGEN 467
15.7.2 PHOSPHORUS 468
15.7.2.1 PHOSPHORUS(O) 468
15.7.2.2 PHOSPHORUS(I) 469
15.7.2.3 PHOSPHORUS(III) 471
15.7.2.4 PHOSPHORUS(V) 472
15.7.3 ARSENIC AND ANTIMONY 473
15.8 NHC COMPLEXES OF GROUP 16 ELEMENTS 474
15.8.1 OXYGEN AND SULFUR 474
15.8.2 SELENIUM 474
15.8.3 TELLURIUM 475
15.9 NHC COMPLEXES OF GROUP 17 ELEMENTS 476
15.10 NHC REACTIVITY WITH PROTIC REAGENTS 477
15.11 CYCLIC ALKYL AMINO CARBENES: CLOSELY RELATED CYCLIC COUSINS
TO NHCS WITH SIMILAR AND DIFFERING REACTIVITIES 478
15.11.1 BORON 479
15.11.2 CARBON 481
15.11.3 SILICON 482
15.11.4 NITROGEN 483
15.11.5 PHOSPHORUS 483
15.12 SUMMARY AND OUTLOOK 487
REFERENCES 488
16 CATALYSIS WITH ACYCLIC AMINOCARBENE LIGANDS: ALTERNATIVES TO
NHCS WITH DISTINCT STERIC AND ELECTRONIC PROPERTIES
499
LEGRANDE M. SLAUGHTER
16.1 INTRODUCTION 499
16.2 METALATION ROUTES OF ACYCLIC CARBENE LIGANDS 500
16.3 LIGAND PROPERTIES OF ACYCLIC CARBENES 502
16.3.1 DONOR ABILITY 502
16.3.2 STRUCTURAL PROPERTIES 503
16.3.3 DECOMPOSITION ROUTES 504
16.4 CATALYTIC APPLICATIONS 505
16.4.1 COUPLING REACTIONS 505
16.4.1.1 SUZUKI-MIYAURA COUPLING 505
16.4.1.2 SONOGASHIRA COUPLING 508
16.4.1.3 HECK COUPLING 508
16.4.1.4 BUCHWALD-HARTWIG AMINATION 509
16.4.2 ALLYLIC ALKYLATIONS 509
CONTENTS
16.4.3 OLEFIN METATHESIS 510
16.4.4 GOLD CATALYSIS 510
16.4.4.1 ENYNE CYCLIZATIONS 511
16.4.4.2 ALLENE AND ALKENE HYDROFUNCTIONALIZATIONS 512
16.4.4.3 ALKYNE FUNCTIONALIZATIONS 512
16.4.5 ENANTIOSELECTIVE CATALYSIS WITH CHIRAL ACYCLIC
CARBENES 513
16.4.5.1 CATALYSIS WITH CHIRAL ADC LIGANDS DERIVED
FROM ISOCYANIDES 514
16.4.5.2 CATALYSIS WITH CHIRAL ADC LIGANDS DERIVED FROM AMIDINIUM
PRECURSORS 516
16.5 FRONTIERS IN ACYCLIC CARBENE CHEMISTRY 516
16.6 CONCLUSION 521
REFERENCES 521
INDEX 525 |
| any_adam_object | 1 |
| author2 | Nolan, Steven P. 1962- |
| author2_role | edt |
| author2_variant | s p n sp spn |
| author_GND | (DE-588)132074303 |
| author_facet | Nolan, Steven P. 1962- |
| building | Verbundindex |
| bvnumber | BV041991339 |
| classification_rvk | VK 5500 VK 7200 |
| ctrlnum | (OCoLC)876382512 (DE-599)DNB1049503341 |
| dewey-full | 547.593044242 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.593044242 |
| dewey-search | 547.593044242 |
| dewey-sort | 3547.593044242 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
| format | Book |
| fullrecord | <?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>00000nam a2200000 c 4500</leader><controlfield tag="001">BV041991339</controlfield><controlfield tag="003">DE-604</controlfield><controlfield tag="005">20160427</controlfield><controlfield tag="007">t</controlfield><controlfield tag="008">140724s2014 gw d||| |||| 00||| eng d</controlfield><datafield tag="015" ind1=" " ind2=" "><subfield code="a">14,N15</subfield><subfield code="2">dnb</subfield></datafield><datafield tag="016" ind1="7" ind2=" "><subfield code="a">1049503341</subfield><subfield code="2">DE-101</subfield></datafield><datafield tag="020" ind1=" " ind2=" "><subfield code="a">3527334904</subfield><subfield code="9">3-527-33490-4</subfield></datafield><datafield tag="020" ind1=" " ind2=" "><subfield code="a">9783527334902</subfield><subfield code="c">Gb. : ca. EUR 149.00 (DE) (freier Pr.), ca. EUR 153.20 (AT) (freier Pr.), ca. sfr 201.00 (freier Pr.)</subfield><subfield code="9">978-3-527-33490-2</subfield></datafield><datafield tag="020" ind1=" " ind2=" "><subfield code="a">9783527671229</subfield><subfield code="c">oBook</subfield><subfield code="9">978-3-527-67122-9</subfield></datafield><datafield tag="024" ind1="3" ind2=" "><subfield code="a">9783527334902</subfield></datafield><datafield tag="028" ind1="5" ind2="2"><subfield code="a">Best.-Nr.: 1133490 000</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(OCoLC)876382512</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-599)DNB1049503341</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-604</subfield><subfield code="b">ger</subfield><subfield code="e">rakddb</subfield></datafield><datafield tag="041" ind1="0" ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="044" ind1=" " ind2=" "><subfield code="a">gw</subfield><subfield code="c">XA-DE-BW</subfield></datafield><datafield tag="049" ind1=" " ind2=" "><subfield code="a">DE-20</subfield><subfield code="a">DE-11</subfield><subfield code="a">DE-355</subfield><subfield code="a">DE-29T</subfield><subfield code="a">DE-19</subfield></datafield><datafield tag="082" ind1="0" ind2=" "><subfield code="a">547.593044242</subfield><subfield code="2">22/ger</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">VK 5500</subfield><subfield code="0">(DE-625)147401:253</subfield><subfield code="2">rvk</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">VK 7200</subfield><subfield code="0">(DE-625)147417:253</subfield><subfield code="2">rvk</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">540</subfield><subfield code="2">sdnb</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">N-heterocyclic carbenes</subfield><subfield code="b">effective tools for organometallic synthesis</subfield><subfield code="c">ed. by Steven P. Nolan</subfield></datafield><datafield tag="263" ind1=" " ind2=" "><subfield code="a">201409</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="a">Weinheim</subfield><subfield code="b">Wiley-VCH</subfield><subfield code="c">2014</subfield></datafield><datafield tag="300" ind1=" " ind2=" "><subfield code="a">XXII, 543 S.</subfield><subfield code="b">graph. Darst.</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="b">txt</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="b">n</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="b">nc</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="650" ind1="0" ind2="7"><subfield code="a">Heterocyclische Verbindungen</subfield><subfield code="0">(DE-588)4159726-6</subfield><subfield code="2">gnd</subfield><subfield code="9">rswk-swf</subfield></datafield><datafield tag="650" ind1="0" ind2="7"><subfield code="a">Carbene</subfield><subfield code="0">(DE-588)4147281-0</subfield><subfield code="2">gnd</subfield><subfield code="9">rswk-swf</subfield></datafield><datafield tag="650" ind1="0" ind2="7"><subfield code="a">Metallorganische Chemie</subfield><subfield code="0">(DE-588)4602390-2</subfield><subfield code="2">gnd</subfield><subfield code="9">rswk-swf</subfield></datafield><datafield tag="650" ind1="0" ind2="7"><subfield code="a">Stickstoffheterocyclen</subfield><subfield code="0">(DE-588)4183269-3</subfield><subfield code="2">gnd</subfield><subfield code="9">rswk-swf</subfield></datafield><datafield tag="655" ind1=" " ind2="7"><subfield code="0">(DE-588)4143413-4</subfield><subfield code="a">Aufsatzsammlung</subfield><subfield code="2">gnd-content</subfield></datafield><datafield tag="689" ind1="0" ind2="0"><subfield code="a">Carbene</subfield><subfield code="0">(DE-588)4147281-0</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="0" ind2="1"><subfield code="a">Stickstoffheterocyclen</subfield><subfield code="0">(DE-588)4183269-3</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="0" ind2="2"><subfield code="a">Metallorganische Chemie</subfield><subfield code="0">(DE-588)4602390-2</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="0" ind2=" "><subfield code="5">DE-604</subfield></datafield><datafield tag="689" ind1="1" ind2="0"><subfield code="a">Heterocyclische Verbindungen</subfield><subfield code="0">(DE-588)4159726-6</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="1" ind2="1"><subfield code="a">Carbene</subfield><subfield code="0">(DE-588)4147281-0</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="1" ind2=" "><subfield code="8">1\p</subfield><subfield code="5">DE-604</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Nolan, Steven P.</subfield><subfield code="d">1962-</subfield><subfield code="0">(DE-588)132074303</subfield><subfield code="4">edt</subfield></datafield><datafield tag="776" ind1="0" ind2="8"><subfield code="i">Erscheint auch als</subfield><subfield code="n">Online-Ausgabe, EPUB</subfield><subfield code="z">978-3-527-67124-3</subfield></datafield><datafield tag="776" ind1="0" ind2="8"><subfield code="i">Erscheint auch als</subfield><subfield code="n">Online-Ausgabe, MOBI</subfield><subfield code="z">978-3-527-67123-6</subfield></datafield><datafield tag="776" ind1="0" ind2="8"><subfield code="i">Erscheint auch als</subfield><subfield code="n">Online-Ausgabe, PDF</subfield><subfield code="z">978-3-527-67125-0</subfield></datafield><datafield tag="856" ind1="4" ind2="2"><subfield code="m">X:MVB</subfield><subfield code="q">text/html</subfield><subfield code="u">http://deposit.dnb.de/cgi-bin/dokserv?id=4624829&prov=M&dok_var=1&dok_ext=htm</subfield><subfield code="3">Inhaltstext</subfield></datafield><datafield tag="856" ind1="4" ind2="2"><subfield code="m">DNB Datenaustausch</subfield><subfield code="q">application/pdf</subfield><subfield code="u">http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027433576&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA</subfield><subfield code="3">Inhaltsverzeichnis</subfield></datafield><datafield tag="883" ind1="1" ind2=" "><subfield code="8">1\p</subfield><subfield code="a">cgwrk</subfield><subfield code="d">20201028</subfield><subfield code="q">DE-101</subfield><subfield code="u">https://d-nb.info/provenance/plan#cgwrk</subfield></datafield><datafield tag="943" ind1="1" ind2=" "><subfield code="a">oai:aleph.bib-bvb.de:BVB01-027433576</subfield></datafield></record></collection> |
| genre | (DE-588)4143413-4 Aufsatzsammlung gnd-content |
| genre_facet | Aufsatzsammlung |
| id | DE-604.BV041991339 |
| illustrated | Illustrated |
| indexdate | 2024-08-03T01:40:01Z |
| institution | BVB |
| isbn | 3527334904 9783527334902 9783527671229 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-027433576 |
| oclc_num | 876382512 |
| open_access_boolean | |
| owner | DE-20 DE-11 DE-355 DE-BY-UBR DE-29T DE-19 DE-BY-UBM |
| owner_facet | DE-20 DE-11 DE-355 DE-BY-UBR DE-29T DE-19 DE-BY-UBM |
| physical | XXII, 543 S. graph. Darst. |
| publishDate | 2014 |
| publishDateSearch | 2014 |
| publishDateSort | 2014 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | N-heterocyclic carbenes effective tools for organometallic synthesis ed. by Steven P. Nolan 201409 Weinheim Wiley-VCH 2014 XXII, 543 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Heterocyclische Verbindungen (DE-588)4159726-6 gnd rswk-swf Carbene (DE-588)4147281-0 gnd rswk-swf Metallorganische Chemie (DE-588)4602390-2 gnd rswk-swf Stickstoffheterocyclen (DE-588)4183269-3 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Carbene (DE-588)4147281-0 s Stickstoffheterocyclen (DE-588)4183269-3 s Metallorganische Chemie (DE-588)4602390-2 s DE-604 Heterocyclische Verbindungen (DE-588)4159726-6 s 1\p DE-604 Nolan, Steven P. 1962- (DE-588)132074303 edt Erscheint auch als Online-Ausgabe, EPUB 978-3-527-67124-3 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-67123-6 Erscheint auch als Online-Ausgabe, PDF 978-3-527-67125-0 X:MVB text/html http://deposit.dnb.de/cgi-bin/dokserv?id=4624829&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=027433576&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis 1\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk |
| spellingShingle | N-heterocyclic carbenes effective tools for organometallic synthesis Heterocyclische Verbindungen (DE-588)4159726-6 gnd Carbene (DE-588)4147281-0 gnd Metallorganische Chemie (DE-588)4602390-2 gnd Stickstoffheterocyclen (DE-588)4183269-3 gnd |
| subject_GND | (DE-588)4159726-6 (DE-588)4147281-0 (DE-588)4602390-2 (DE-588)4183269-3 (DE-588)4143413-4 |
| title | N-heterocyclic carbenes effective tools for organometallic synthesis |
| title_auth | N-heterocyclic carbenes effective tools for organometallic synthesis |
| title_exact_search | N-heterocyclic carbenes effective tools for organometallic synthesis |
| title_full | N-heterocyclic carbenes effective tools for organometallic synthesis ed. by Steven P. Nolan |
| title_fullStr | N-heterocyclic carbenes effective tools for organometallic synthesis ed. by Steven P. Nolan |
| title_full_unstemmed | N-heterocyclic carbenes effective tools for organometallic synthesis ed. by Steven P. Nolan |
| title_short | N-heterocyclic carbenes |
| title_sort | n heterocyclic carbenes effective tools for organometallic synthesis |
| title_sub | effective tools for organometallic synthesis |
| topic | Heterocyclische Verbindungen (DE-588)4159726-6 gnd Carbene (DE-588)4147281-0 gnd Metallorganische Chemie (DE-588)4602390-2 gnd Stickstoffheterocyclen (DE-588)4183269-3 gnd |
| topic_facet | Heterocyclische Verbindungen Carbene Metallorganische Chemie Stickstoffheterocyclen Aufsatzsammlung |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=4624829&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=027433576&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT nolanstevenp nheterocycliccarbeneseffectivetoolsfororganometallicsynthesis |