Catalytic arylation methods: from the academic lab to industrial processes
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| Sprache: | English |
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[2015]
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| Beschreibung: | XIX, 502 Seiten Illustrationen, Diagramme |
| ISBN: | 9783527335183 3527335188 |
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| 245 | 1 | 0 | |a Catalytic arylation methods |b from the academic lab to industrial processes |c Anthony J. Burke and Carolina Silva Marques |
| 264 | 1 | |a Weinheim |b Wiley-VCH |c [2015] | |
| 264 | 4 | |c © 2015 | |
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CONTENTS
PREFACE XV
LIST OF ABBREVIATIONS XVII
1 CROSS-COUPLING ARYLATIONS: PRECEDENTS AND RAPID HISTORICAL REVIEW OF
THE FIELD 1
1.1 METAL-CATALYZED CROSS-COUPLINGS: FROM ITS ORIGINS TO THE NOBEL PRIZE
AND BEYOND I
1.2 ARYLATION: WHAT IS SO SPECIAL? 12
1.3 RECENT NEW DEVELOPMENTS 14
1.3.1 ARYLATIONS WITH THE HECK-MIZOROKI REACTION 14
1.3.2 ARYLATIONS WITH THE HECK-MATSUDA REACTION-RECENT DEVELOPMENTS 43
1.3.3 HIYAMA-HATANAKA CROSS-COUPLING REACTION 46
1.3.4 ARYLATIONS WITH THE STILLE REACTION 48
1.3.5 ARYLATIONS WITH THE SONOGASHIRA-HAGIHARA REACTION 48
1.3.6 ARYLATIONS WITH THE SUZUKI-MIYAURA REACTION 55
1.3.7 TAMAO-KUMADA-CORRIU CROSS COUPLING 75
1.3.8 NEGISHI-BABA CROSS-COUPLING
78
1.3.9 BEYOND THE ULLMANN AND SUZUKI-MIYAURA REACTIONS, OTHER NEWER
APPROACHES TO
FUNCTIONAL BIARYL SYNTHESIS: PD, FE, CO, AND OTHER METALS 83
1.3.9.1 WITH PALLADIUM 83
1.3.9.2 WITH IRON 84
1.3.9.3 WITH NICKEL 84
1.3.9.4 WITH COBALT 84
1.3.10 CONCLUSIONS 84
1.4 SELECTED EXPERIMENTS FROM THE LITERATURE 85
1.4.1 THE HECK-MIZOROKI REACTION 85
1.4.1.1 HETEROGENEOUS CATALYTIC SYNTHESIS OF ()-BUTYL CINNAMATE USING A
PALLADIUM
NANOSPHERE CATALYST 85
1.4.1.2 THE PREPARATIVE CATALYTIC SYNTHESIS OF
5-(^-TRIFLUOROMETHYLPHENYL)-2,3-DIHYDROFURAN IN
CONTINUOUS FLOW 85
1.4.2 THE HECK-MATSUDA REACTION 85
1.4.2.1 CATALYTIC SYNTHESIS OF ()-3-(4-METHOXYPHENYL)ACRYLIC ACID USING
PALLADIUM ACETATE IN
WATER 85
1.4.2.2 CATALYTIC SYNTHESIS OF 2-PHENYL- 1/F-INDENE USING COPPER
CHLORIDE 86
1.4.2.3 CATALYTIC SYNTHESIS OF ()-ETHYL 3-(4-METHOXYPHENYL)ACRYLATE
USING PALLADIUM
NANOPARTICLES SUPPORTED ON AGAROSE HYDROGEL 86
1.4.3 THE HECK-HIYAMA REACTION 87
1.4.3.1 CATALYTIC SYNTHESIS OF /?-NITROBIPHENYL: LIGAND-FREE COUPLING
USING PD/C 87
1.4.4 THE STILLE REACTION 87
1.4.4.1 THE CU CATALYZED STILLE REACTION - SYNTHESIS OF
N
-ETHYL-7V-
(PHENYL-/?-TOLYLMETHYL)BENZAMIDE 87
1.4.5 THE SONOGASHIRA-HAGIHARA REACTION 87
1.4.5.1 THE COPPER-FREE CATALYTIC SYNTHESIS OF DIPHENYLETHYNE 87
1.4.5.2 SONOGASHIRA-HAGIHARA CROSS-COUPLING WITH ARENEDIAZONIUM SALTS -
SYNTHESIS OF
L-(4-METHOXYPHENYL)-2-PHENYLACETYLENE 87
1.4.6 THE SUZUKI-MIYAURA REACTION 88
1.4.6.1 SYNTHESIS OF 4-(2,6-DIMETHYLPHENYL)-3,5-DIMETHYLISOXAZOLE USING
PD-PEPPSI-IPENT 88
1.4.6.2 SYNTHESIS /?-PHENYLANISOLE VIA THE SUZUKI-MIYAURA REACTION WITH
A FIB RECAT-1034
CATALYST 88
1.4.7 TAMAO-KUMADA-CORRIU CROSS-COUPLING REACTION 88
1.4.7.1 SYNTHESIS OF 2-(4-METHOXYPHENYL)PYRIDINE 88
1.4.8 NEGISHI-BABA CROSS-COUPLING 89
1.4.8.1 SYNTHESIS OF 1 -MESITYLNAPHTHALENE 89
1.4.9 BIARYL SYNTHESIS WITH THE HINDERED ARYLLITHIUM REAGENT,
2,6-DIMETHOXYPHENYLLITHIUM:
CATALYTIC SYNTHESIS OF L,3-DIMETHOXY-2-(L-NAPHTHYL)BENZENE 89
REFERENCES 89
2 AMINE, PHENOL, ALCOHOL, AND THIOL ARYLATION 95
2.1 INTRODUCTION 95
2.2 PD-CATALYZED PROCESSES 98
2.2.1 BUCHWALD - HARTWIG ARYLATIONS (CAR - NR BOND FORMATION)
98
2.2.2 MIGITA THIOETHER SYNTHESIS (CAR - SR BOND FORMATION)
109
2.2.3 ARYLETHER SYNTHESIS (CAR - OR BOND FORMATION)
113 *
2.2.4 PHOSPHOROUS ARYLATIONS (CAR - P BOND FORMATION)
117
2.2.4.1 PD-CATALYZED PHOSPHOROUS ARYLATIONS (CAR - P BOND FORMATION)
117
2.3 CU-CATALYZED AND PROMOTED ARYLATIONS: (CAR-N BOND FORMATION)
118
2.3.1 ARYLAMINES (C-N BOND FORMATION) 118
2.3.1.1 THE MODIFIED ULLMANN REACTION (ULLMANN-CONDENSATION-TYPE
ARYLATIONS) 118
2.3.1.2 USE OF ARYLBORONIC ACIDS AND DERIVATIVES INSTEAD OF ARYLHALIDES:
CHAN - LAM - EVANS
COUPLING AND OTHER VARIANTS 123
2.3.2 ARYLTHIOETHERS (CAR-S BOND FORMATION) 128
2.3.2.1 USE OF ARYLHALIDES 128
23.2.2 THE CHAN - LAM - EVANS VARIANT (USE OF ARYLBORONIC ACIDS)
129
2.3.3 ARYLETHERS (CAR-
0 BOND FORMATION)
129
2.3.3.1 THE COPPER-CATALYZED ULLMANN COUPLING REACTION 129
2.33.2 THE CHAN-LAM-EVANS REACTION 131
2.3.4 PHOSPHOROUS ARYLATIONS (CAR - P BOND FORMATION)
133
2.4 FE-CATALYZED ARYLATIONS 134
2.4.1 FE-CATALYZED ARYL AMINATION: (CAR-N BOND FORMATION)
136
2.4.2 ARYLETHERS (CAR-
0 BOND FORMATION)
136
2.4.3 ARYLTHIOETHERS (CAR-S BOND FORMATION) 136
2.5 NI-CATALYZED REACTIONS 137
2.5.1 NI-CATALYZED AMINE ARYLATION: (CAR-N BOND FORMATION)
137
2.5.2 NI-CATALYZED SULFIDE ARYLATION: (CAR-S BOND FORMATION) 138
2.5.3 NI-CATALYZED PHOSPHOROUS ARYLATIONS (CAR-P BOND FORMATION)
138
2.6 CO-CATALYZED ARYLATIONS 139
2.6.1 CO-CATALYZED AMINE ARYLATIONS: (CAR - N BOND FORMATION)
139
2.6.2 CO-CATALYZED SULFIDE ARYLATION: (CAR-S BOND FORMATION) 139
2.7 MN-CATALYZED ARYLATIONS 140
2.7.1 MN-CATALYZED AMINE ARYLATIONS: (CAR -N BOND FORMATION)
140
2.7.2 MN-CATALYZED SULFIDE ARYLATION: (CAR - S BOND FORMATION)
140
2.8 CD-CATALYZED ARYLATIONS 140
2.8.1 CD-CATALYZED ARYL AMINATION: (CAR-N BOND FORMATION)
140
2.9 BI(III) AND INDIUM OXIDE-CATALYZED THIOL ARYLATIONS 141
2.10 CONCLUSIONS AND FINAL COMMENT 141
2.11 SELECTED EXPERIMENTS FROM THE LITERATURE 141
2.11.1 AMINE ARYLATIONS 141
2.11.1.1 THE BUCHWALD - HARTWIG AMINE ARYLATION
141
2.11.1.2 COPPER-CATALYZED AMINE ARYLATIONS 142
2.11.1.3 FE ARYLATIONS 143
2.11.2 THIOL ARYLATION 143
2.11.2.1 PALLADIUM-CATALYZED ARYLATION 143
2.11.2.2 COPPER-CATALYZED THIOL ARYLATION 144
2.11.2.3 FE CATALYSIS 144
2.11.3 ETHERIFICATION CROSS-COUPLING REACTIONS 144
2.11.3.1 WITH PALLADIUM 144
2.11.3.2 WITH IRON 145
REFERENCES 145
3 DECARBOXYLATIVE COUPLING TECHNIQUES 151
3.1 INTRODUCTION 151
3.2 PD-CATALYZED VERSIONS 152
3.2.1 PD-BASED SYSTEMS 152
3.2.2 PD/CU-BASED SYSTEMS 159
3.3 OTHER METAL-CATALYZED VERSIONS 163
3.3.1 CU-BASED SYSTEMS 163
3.3.2 OTHER METAL-BASED SYSTEMS 165
3.4 CONCLUSIONS 166
3.5 SELECTED EXPERIMENTS 169
3.5.1 APPLICATION OF PD CATALYSTS 169
3.5.1.1 SYNTHESIS OF 2-(3-PYRIDYL)-L-METHYLPYRROLE 169
3.5.1.2 SYNTHESIS OF
L-METHYL-2,3-BIS(4-(TRIFLUOROMETHYL)PHENYL)-L/F-INDOLE 169
3.5.1.3 SYNTHESIS OF 2,6-DIMETHOXYBIPHENYL 169
3.5.1.4 SYNTHESIS OF
7-(DIETHYLAMINO)-3-(4-METHOXYPHENYL)-2//-CHROMEN-2-ONE 169
3.5.1.5 SYNTHESIS OF 4-(2-NITROPHENYL)BENZOPHENONE 170
3.5.1.6 SYNTHESIS OF 3,4'-DIMETHYL-4-NITROBIPHENYL 170
3.5.1.7 SYNTHESIS OF 4-METHYLBENZOPHENONE 170
3.5.1.8 SYNTHESIS OF N-[(L-NAPHTHYL)(PHENYL)METHYLENE]CYCLOHEXANAMINE
170
3.5.1.9 SYNTHESIS OF 2,3,4,5,6-PENTAFLUORO-2'-METHYLBIPHENYL 171
REFERENCES 171
4 C-H BOND ACTIVATION FOR ARYLATIONS 173
4.1 INTRODUCTION 173
4.2 C(SP2)-H ACTIVATIONS 176
4.2.1 INVOLVING AR/AR COUPLINGS C(SP2)-H ACTIVATIONS 176
4.2.1.1 DIRECTED METALATING GROUP (DMG)-ASSISTED C(SP2)-H ACTIVATIONS
DIRECT
ARYLATION 176
4.2.2 INVOLVING AR/C=X (X - C, O, N) COUPLINGS C(SP2)-H ACTIVATIONS
194
4.2.2.1 DMG AR/C=X (X - C, O, N) COUPLINGS C(SP2)-H ACTIVATIONS 194
422
2
NON-DMG AR/C=X (X = C, 0, N) COUPLINGS C(SP2)-H ACTIVATIONS 216
4.2.3
4.2.3.1
4.2.3.2
4.2.4
4.2.4.1
4.2A2
4.2.5
4.2.6
4.3
4.4
4.4.1
4.4.1.1
4.4.1.2
4.4.1.3
4.4.2
4.4.2.1
4.4.2.2
4.4.3
4.4.3.1
5
5.1
5.2
5.3
5.4
5.4.1
5.4.2
5.4.3
5.5
5.6
5.6.1
5.6.1.1
5.6.1.2
5.6.1.3
5.6.2
5.6.2.1
5.6.3
5.6.3.1
6
6.1
6.2
6.3
6.4
6.4.1
6.4.2
INVOLVING AR/ALKYNE COUPLINGS C(SP2)-H ACTIVATIONS 217
DMG AR/ALKYNE COUPLINGS C(SP2)-H ACTIVATIONS 217
NON-DMG AR/ALKYNE COUPLINGS C(SP2)-H ACTIVATIONS 229
INVOLVING AR/ALKYL COUPLINGS 229
DMG ASSISTED AR/ALKYL COUPLINGS C(SP2)-H ACTIVATIONS 231
NON-DMG ASSISTED AR/ALKYL COUPLINGS C(SP2)-H ACTIVATIONS 235
INVOLVING AR/N COUPLINGS C(SP2)-H ACTIVATIONS 239
INVOLVING AR/OTHER HETEROATOM COUPLINGS 240
CONCLUSIONS 240
SELECTED EXPERIMENTS FROM THE LITERATURE 240
CAR-H ARYLATION 240
WITH PALLADIUM 240
WITH RHODIUM 241
WITH RUTHENIUM 242
CAR-H C=X (X = C, O, N) CROSS-COUPLING 242
WITH RHODIUM 242
WITH RUTHENIUM 242
CAR-H ALKYNE CROSS-COUPLINGS 243
WITH RHODIUM 243
REFERENCES 243
CONJUGATE ADDITIONS 247
CONJUGATE ADDITIONS: A POWERFUL TOOL FOR APPENDING ORGANIC RESIDUES TO
CYCLIC AND
ACYCLIC SUBSTRATES 247
APPLICATIONS OF RH CATALYSTS 248
APPLICATIONS OF PD CATALYSTS 270
APPLICATIONS OF RU AND OTHER CATALYSTS 279
RUTHENIUM 279
COPPER 280
NICKEL 285
CONCLUSIONS 286
SELECTED EXPERIMENTS 287
APPLICATION OF RH CATALYSTS 287
SYNTHESIS OF (S)-3-PHENYLCYCLOHEXANONE 287
SYNTHESIS OF A BIDENTATE PHOSPHORAMIDITE LIGAND: M/V-DIMETHYL
(R,R)-0-LINKED-
PHOSPHORAMIDITE
287
SYNTHESIS OF (R)-3-(2-NAPHTHYL)CYCLOHEXANONE 287
APPLICATION OF PD CATALYSTS 287
SYNTHESIS OF (-)-2-(BIPHENYL-4-YL)-4-OXO-PIPERIDINE-L-CARBOXYLIC ACID
TERT-BUTYL
ESTER 287
APPLICATION OF CU CATALYSTS 288
SYNTHESIS OF (R)-(+)-3-ETHYL-3-METHYLCYCLOHEXANONE 288
REFERENCES 288
IMINE ARYLATIONS - SYNTHESIS OF ARYLAMINES 292
ARYLATION OF C=N BONDS: SIMPLE ACCESS TO CHIRAL AMINE UNITS 292
APPLICATION OF RH CATALYSTS 292
APPLICATION OF PD CATALYSTS 305
APPLICATION OF RU AND OTHER CATALYSTS 313
RUTHENIUM 313
ZINC 314
6.4.3 COPPER 314
6.5 THE PETASIS- AKRITOPOULOU REACTION
315
6.6 CONCLUSIONS 322
6.7 SELECTED EXPERIMENTS 324
6.7.1 APPLICATION OF RH CATALYSTS 324
6.7.1.1 SYNTHESIS OF
(S)-TV-[(2-FURYL)PHENYLMETHYL]-4-METHYLBENZENESULFONAMIDE 324
6.7.1.2 SYNTHESIS OF TV-(1 - (4-CHLOROPHENYL)-1
-PHENYLPROPYL)-TOSYLAMIDE 324
6.7.1.3 SYNTHESIS OF TV-((4-METHOXY-2-METHYLPHENYL)(PHENYL)METHYL)-4-
NITROBENZENESULFONAMIDE 324
6.7.2 APPLICATION OF PD CATALYSTS 325
6.7.2.1 SYNTHESIS OF [(4-FLUOROPHENYL)PHENYLMETHYL]CARBAMIC ACID
TERT-BUTYL ESTER 325
6.7.3 APPLICATION OF RU AND OTHER CATALYSTS 325
6.7.3.1 SYNTHESIS OF
TV-[(2-CHLOROPHENYL)(PHENYL)METHYL]-4-METHYLBENZENESULFONAMIDE 325
6.7.3.2 SYNTHESIS OF ETHYL 2-(4-(DIMETHYLAMINO)PHENYL)-2
((METHOXYCARBONYL)AMINO)
ACETATE 325
6.7.4 THE PETASIS-AKRITOPOULOU REACTION 326
6.7.4.1 SYNTHESIS OF ()-7V-(DIPHENYLMETHYL)-A-PHENYLGLYCINE 326
6.7A2 SYNTHESIS OF
(R)-2-((4-(BENZYLOXY)PHENYL)(PYRROLIDIN-L-YL)METHYL)PHENOL 326
6.7.4.3 SYNTHESIS OF ETHYL 2-PHENYL-2-(PYRROLIDIN-L-YL)ACETATE 326
REFERENCES 326
7 CARBONYL GROUP ARYLATION 329
7.1 INTRODUCTION 329
7.2 APPLICATION OF RH CATALYSTS 329
7.2.1 ADDITIONS TO ALDEHYDES 330
7.2.2 ADDITION TO KETONES 342
7.3 APPLICATION OF PD CATALYSTS 349
7.4 APPLICATION OF RU AND OTHER CATALYSTS 355
7.4.1 RUTHENIUM CATALYSIS 355
7.4.2 NICKEL CATALYSIS 357
7.4.3 COPPER CATALYSIS 361
7.4.4 PLATINUM CATALYSIS 362
7.4.5 IRON CATALYSIS 363
7.4.6 ZINC CATALYSIS 365
7.4.7 TITANIUM CATALYSIS 367
7.5 CONCLUSIONS 370
7.6 SELECTED EXPERIMENTS
370
7.6.1 APPLICATION OF RH CATALYSTS 370
7.6.1.1 SYNTHESIS OF (R)-(L-NAPHTHYL)PHENYLMETHANOL 370
7.6.1.2 SYNTHESIS OF (5)-(2-CHLOROPHENYL) (MESITYL)METHANOL 370
7.6.1.3 SYNTHESIS OF (R)-BENZO[FIF] [L,3]DIOXOL-5-YL(PHENYL)METHANOL 372
7.6.1.4 SYNTHESIS OF 1 -/?-TOLYL-1,2,3,4-TETRAHYDRONAPHTHALEN-1 -OL 371
7.6.1.5 SYNTHESIS OF (S)-5-CHLORO-3-(3,5-DIMETHYLPHENYL)-3-HYDROXY-L
(4-METHOXYBENZYL)INDOLIN-2-ONE 371
7.6.2 APPLICATION OF PD CATALYSTS 372
7.6.2.1 SYNTHESIS OF 3-PHENYL-3-HYDROXY-2,3-DIHYDROBENZOFURAN 372
7.6.3 APPLICATION OF RU CATALYSTS
372
7.6.3.1 SYNTHESIS OF (S)-(4-CHLOROPHENYL)PHENYLMETHANOL 372
7.6.4 APPLICATION OF CU CATALYSTS 372
7.6.4.1 SYNTHESIS OF (S)-(4-CHLOROPHENYL)(PHENYL)METHANOL 372
7.6.5 APPLICATION OF ZN CATALYSTS 372
7.6.5.1 SYNTHESIS OF (R)-(CYCLOHEXYL)PHENYLMETHANOL 372
7.6.5.2 SYNTHESIS OF (2?)-2,2-DIMETHYL-L-PHENYLPROPANOL 372
7.6.5.3 SYNTHESIS OF 1 -(4'-METHYLPHENYL)-1 -PHENYLETHANOL 373
REFERENCES 373
8 A-ARYLATION PROCESSES 376
8.1 INTRODUCTION 376
8.2 ARYLATION OF ENOLATES AND EQUIVALENTS 377
8.2.1 ARYLATION OF KETONES AND ALDEHYDES 377
8.2.1.1 KETONES 377
8.2.1.2 ALDEHYDES 397
8.2.2 ARYLATION OF AMIDES 399
8.2.3 ARYLATION OF ESTERS 412
8.3 OTHER METAL-CATALYZED A-ARYLATIONS 419
8.3.1 COPPER CATALYSTS 419
8.3.2 NICKEL CATALYSTS 425
8.4 CONCLUSIONS 427
8.5 SELECTED EXPERIMENTS 428
8.5.1 ARYLATION OF ENOLATES AND EQUIVALENTS 428
8.5.1.1 SYNTHESIS OF 2-(4-BIPHENYL)-4-METHYL-3-PENTANONE 428
8.5.1.2 SYNTHESIS OF A-(O-TOLYL) ACETOPHENONE 430
8.5.1.3 SYNTHESIS OF L-BENZYL-4-METHYL-L,2,3,4-TETRAHYDRO-4-QUINOLINOL
430
8.5.1.4 SYNTHESIS OF (2?)-L,3-DIMETHYL-3-PHENYLINDOLIN-2-ONE 430
8.5.1.5 SYNTHESIS OF TERT-BUTYL (6-METHOXYNAPHTHALEN-2-YL)ACETATE 430
8.5.1.6 SYNTHESIS OF TERT-BUTYL A-MESITYLPROPANOATE 430
8.5.2 OTHER METAL-CATALYZED A-ARYLATIONS 431
8.5.2.1 SYNTHESIS OF
L-BENZYL-6-CHLORO-5-FLUORO-3-(L-HYDROXYETHYLIDENE)INDOLIN-2-ONE 431
8.5.2.2 SYNTHESIS OF (S)-2-PHENYL-L-OCTANOL 431
8.5.2.3 SYNTHESIS OF
2-METHYL-2-(4-(TRIFLUOROMETHYL)PHENYL)-2,3-DIHYDRO-L//-INDEN-L-ONE
431
REFERENCES 432
9 CATALYTIC CYCLOADDITION AROMATIZATION PROCESSES 436
9.1 INTRODUCTION 436
9.2 CYCLOADDITION EVENTS 436
9.2.1 [2+2+2] CYCLOADDITIONS 436
9.2.1.1 WITH RHODIUM 437
9.2.1.2 WITH COBALT 443
9.2.1.3 WITH RUTHENIUM 445
9.2.1.4 WITH PALLADIUM 448
9.2.1.5 WITH IRON 452
9.2.1.6 WITH NICKEL 452
9.2.1.7 WITH TITANIUM 452
9.2.1.8 WITH IRIDIUM 454
9.2.1.9 WITH COPPER 454
9.2.2 [3+2]-CYCLOADDITIONS FOR THE SYNTHESIS OF AROMATIC COMPOUNDS 455
9.2.2.1 THE HUIGSENS REACTION 455
9.2.2.2 TETRAZOLE SYNTHESIS 469
9.2.2.3 PYRROLE SYNTHESIS 472
9.2.2.4 THE DIELS-ALDER REACTION 474
9.3 RADICAL-BASED CYCLOAROMATIZATION PROCESSES 474
9.3.1 THE CATALYTIC BERGMAN CYCLIZATION 474
9.3.2 THE CATALYTIC MYERS-SAITO CYCLIZATION 481
9.4 CONCLUSIONS 482
9.5 SELECTED EXPERIMENTS FROM THE LITERATURE 482
9.5.1 [2+2+2]-CYCLOADDITION 482
9.5.1.1 RHODIUM-CATALYZED SYNTHESIS OF 2, 4, 5, 7-TETRAPHENYLISOINDOLINE
482
9.5.1.2 COBALT CATALYZED SYNTHESIS OF
2-(2-METHOXY-L-NAPHTHYL)-6-PHENYL-7,8-DIHYDRO-5H-CYCLOPENTA-[C]PYRIDINE
482
9.5.1.3 PALLADIUM-CATALYZED SYNTHESIS OF AN AROMATIC HEXA-ESTER 483
9.5.1.4 IRON-CATALYZED SYNTHESIS OF 3,6-DIMETHYL-2--BUTYL PYRIDINE 483
9.5.2 [3+2]-CYCLOADDITION: CLICK-CHEMISTRY 484
9.5.2.1 CU-CATALYZED SYNTHESIS OF 17-[3-(L-(L,2,3-TRIAZOLYL))]ESTRADIOL
484
9.5.2.2 ORGANOCATALYTIC SYNTHESIS OF 1,5-DIPHENYL-1//-1,2,3-TRIAZOLE 484
9.5.2.3 CUI-NBS-MEDIATED SYNTHESIS OF
AF-[5'/-(PHENYLTHIO)PHOSPHORYLETHOXYETHYL]-2',3'-0-
ISOPROPYLIDENE-5'-PHOSPHORYL-5-I-L,2,3-TNAZOLE-4-AMIDE-L-D-RIBOFURANOSIDE
485
9.5.2.4 RU-CATALYZED SYNTHESIS OF L-BENZYL-5-PHENYL-L//-L,2,3-TRIAZOLE
485
9.5.2.5 SYNTHESIS OF L-(2-METHYLBENZYL)-5-BENZOYL TETRAZOLE 485
9.5.2.6 CATALYTIC SYNTHESIS OF DIMETHYL
3-CYCLOPROPYL-L//-PYRROLE-2,4-DICARBOXYLATE 486
REFERENCES 486
INDEX 491 |
| any_adam_object | 1 |
| author | Burke, Anthony J. Silva Marques, Carolina 1981- |
| author_GND | (DE-588)1127872001 (DE-588)1127872338 |
| author_facet | Burke, Anthony J. Silva Marques, Carolina 1981- |
| author_role | aut aut |
| author_sort | Burke, Anthony J. |
| author_variant | a j b aj ajb m c s mc mcs |
| building | Verbundindex |
| bvnumber | BV042282948 |
| classification_rvk | VK 6000 |
| ctrlnum | (OCoLC)881386515 (DE-599)DNB1051706807 |
| 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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| id | DE-604.BV042282948 |
| illustrated | Illustrated |
| indexdate | 2025-03-10T13:01:12Z |
| institution | BVB |
| isbn | 9783527335183 3527335188 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-027720276 |
| oclc_num | 881386515 |
| open_access_boolean | |
| owner | DE-29T DE-19 DE-BY-UBM DE-11 DE-83 |
| owner_facet | DE-29T DE-19 DE-BY-UBM DE-11 DE-83 |
| physical | XIX, 502 Seiten Illustrationen, Diagramme |
| publishDate | 2015 |
| publishDateSearch | 2015 |
| publishDateSort | 2015 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Burke, Anthony J. Verfasser (DE-588)1127872001 aut Catalytic arylation methods from the academic lab to industrial processes Anthony J. Burke and Carolina Silva Marques Weinheim Wiley-VCH [2015] © 2015 XIX, 502 Seiten Illustrationen, Diagramme txt rdacontent n rdamedia nc rdacarrier Katalyse (DE-588)4029921-1 gnd rswk-swf Arylierung (DE-588)4387576-2 gnd rswk-swf Arylierung Katalyse Organische Chemie Arylierung (DE-588)4387576-2 s Katalyse (DE-588)4029921-1 s DE-604 Silva Marques, Carolina 1981- Verfasser (DE-588)1127872338 aut X:MVB text/html http://deposit.dnb.de/cgi-bin/dokserv?id=4680898&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=027720276&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Burke, Anthony J. Silva Marques, Carolina 1981- Catalytic arylation methods from the academic lab to industrial processes Katalyse (DE-588)4029921-1 gnd Arylierung (DE-588)4387576-2 gnd |
| subject_GND | (DE-588)4029921-1 (DE-588)4387576-2 |
| title | Catalytic arylation methods from the academic lab to industrial processes |
| title_auth | Catalytic arylation methods from the academic lab to industrial processes |
| title_exact_search | Catalytic arylation methods from the academic lab to industrial processes |
| title_full | Catalytic arylation methods from the academic lab to industrial processes Anthony J. Burke and Carolina Silva Marques |
| title_fullStr | Catalytic arylation methods from the academic lab to industrial processes Anthony J. Burke and Carolina Silva Marques |
| title_full_unstemmed | Catalytic arylation methods from the academic lab to industrial processes Anthony J. Burke and Carolina Silva Marques |
| title_short | Catalytic arylation methods |
| title_sort | catalytic arylation methods from the academic lab to industrial processes |
| title_sub | from the academic lab to industrial processes |
| topic | Katalyse (DE-588)4029921-1 gnd Arylierung (DE-588)4387576-2 gnd |
| topic_facet | Katalyse Arylierung |
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