Innovative catalysis in organic synthesis: oxidation, hydrogenation, and C-X bond forming reactions
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| Language: | English |
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Weinheim
Wiley-VCH
2012
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| Online Access: | Inhaltstext Inhaltsverzeichnis Inhaltsverzeichnis |
| Item Description: | Literaturangaben |
| Physical Description: | XVIII, 356 S. graph. Darst. |
| ISBN: | 3527330976 9783527330973 9783527646586 |
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| 245 | 1 | 0 | |a Innovative catalysis in organic synthesis |b oxidation, hydrogenation, and C-X bond forming reactions |c ed. by Pher G. Andersson |
| 264 | 1 | |a Weinheim |b Wiley-VCH |c 2012 | |
| 300 | |a XVIII, 356 S. |b graph. Darst. | ||
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Record in the Search Index
| _version_ | 1817590365146841088 |
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| adam_text |
IMAGE 1
CONTENTS
FOREWORD X I
LIST O F CONTRIBUTORS X I I I
PART I OXIDATION REACTIONS 1
1 POLYOXOMETALATES A S H O M O G E N E O U S OXIDATION CATALYSTS 3
MAURO CARRARO, ANDREA SARTOREL, MASOOMA IBRAHIM, NADEEN NSOULI, CLAIRE
JAHIER, SYLVAIN MATE, ULRICH KORTZ, A N D MARCELLA BONCHIO 1.1 SOLUBLE
METAL OXIDES AS OXIDATION CATALYSTS 3
1.2 H O M O G E N E O U S OXIDATIONS W I T H P O M S BASED ONLY O N
MO(VI), W(VI), V(V) A D D E N D A IONS 6 1.2.1 OXIDATION W I T H H Y D R
O G E N PEROXIDE B Y
PEROXOPOLYOXOTUNGSTATES-DENDRIMERS 8
1.2.2 H O M O G E N E O U S OXIDATION W I T H H Y D R O G E N PEROXIDE I
N T H E P R E S E N C E O F VACANT A N D H Y B R I D P O M S 10 1.3 H O
M O G E N E O U S OXIDATIONS W I T H T M S - P O M S 12
1.3.1 PEROXOPOLYOXOMETALATES O F H F / Z R 13
1.3.2 AEROBIC OXIDATIONS WITH POLYOXOPALLADATES 16
1.3.3 T M S P S AS OXYGEN-EVOLVING CATALYSTS 17
1.4 CONCLUSIONS 19
A C K N O W L E D G M E N T S 19 REFERENCES 2 0
2 BIOINSPIRED OXIDATIONS CATALYZED BY N O N H E M E IRON A N D M A N G A
N E S E
COMPLEXES 2 7
ISAAC GARCIA-BOSCH, IRENE PRAT, XAVI RIBAS, A N D MIQUEL COSTAS 2.1
INTRODUCTION 2 7
2.2 CATALYTIC OXIDATION O F C = C B O N D S BY N O N H E M E I R O N A N
D M A N G A N E S E
COMPLEXES 2 7
2.2.1 EPOXIDATION 2 7
2.2.1.1 IRON-BASED CATALYSTS 2 7
2.2.1.2 MANGANESE-BASED CATALYSTS 3 0
2.2.2 RIS-DIHYDROXYLATION 3 4
HTTP://D-NB.INFO/1016558597
IMAGE 2
V I C O N T E N T S
2.2.2.1 IRON-BASED CATALYSTS 3 4
2.2.2.2 MANGANESE-BASED CATALYSTS 3 7
2.3 CATALYTIC OXIDATION O F C - H BONDS B Y N O N H E M E I R O N A N D
M A N G A N E S E
COMPLEXES 3 8
2.3.1 HYDROXYLATION 3 8
2.3.1.1 IRON-BASED CATALYSTS 3 8
2.3.1.2 MANGANESE-BASED CATALYSTS 4 0
2.3.2 DESATURATION 41
2.3.2.1 IRON-BASED CATALYSTS 41
2.3.2.2 MANGANESE-BASED CATALYSTS 4 2
REFERENCES 43
3 THE FABULOUS DESTINY O F SULFENIC ACIDS 47
MARIA CHIARA AVERSA, PAOLA BONACCORSI, DAVID MADEC, GUILLAUME PRESTAT, A
N D GIOVANNI POLL 3.1 INTRODUCTION 4 7
3.2 SYNTHESIS O F STABLE SULFENIC ACIDS 4 8
3.3 G E N E R A T I O N O F T R A N S I E N T SULFENIC ACIDS 5 2
3.4 REACTIVITY O F SULFENIC ACIDS I N T H E PREPARATION O F SULFOXIDES A
N D
U N S Y M M E T R I C A L DISULFIDES 5 7 3.5 SYNTHESIS O F STABLE
SULFENATE A N I O N S 62
3.6 G E N E R A T I O N O F T R A N S I E N T SULFENATE A N I O N S
LEADING TO SULFOXIDES 6 5
3.7 CONCLUSIONS 73
REFERENCES 73
4 SUSTAINABLE CATALYTIC OXIDATIONS WITH PEROXIDES 7 7
ISABEL W.C.E. ARENDS, VALERIA CONTE, A N D GIULIA LICINI 4.1
INTRODUCTION 7 7
4.2 METAL-BASED SELECTIVE OXIDATIONS 78 ^
4.2.1 B R O M I N A T I O N REACTIONS 78
4.2.2 OXIDATION O F NITROGEN-CONTAINING SUBSTRATES 8 5
4.2.3 OXIDATION O F SULFUR-CONTAINING SUBSTRATES 8 5
4.2.4 OXIDATION O F ALKENES 8 9
4.3 BIOCATALYTIC OXIDATIONS WITH H Y D R O G E N PEROXIDE 92
4.3.1 W H Y E N Z Y M E S A N D H O O H ? 92
4.3.2 BIOCATALYTIC SULFOXIDATION 9 5
4.3.3 BIOCATALYTIC ALKENES EPOXIDATION 96
4.3.4 BIOCATALYTIC ALCOHOLS OXIDATION 98
4.4 CONCLUSIONS 99
A C K N O W L E D G M E N T S 99 REFERENCES 100
IMAGE 3
CONTENTS | V I I
PART II HYDROGENATION A N D REDUCTION REACTIONS 103
5 ASYMMETRIC HYDROGENATION O F DEHYDROAMINO ACID DERIVATIVES BY
RH-CATALYSTS WITH CHIRAL MONODENTATE P-LIGANDS 105 SERAFINO GLADIALI,
ELISABETTA ALBERICO, A N D ILYA GRIDNEV
5.1 INTRODUCTION 105
5.2 CHIRAL M O N O D E N T A T E P H O S P H O R U S LIGANDS I N A S Y M
M E T R I C
H Y D R O G E N A T I O N 108
5.3 CATALYST PRECURSORS 112
5.4 MECHANISTIC INSIGHTS 117
5.5 F O R M A T I O N O F T H E MAC ADDUCTS 121
5.6 EVOLUTION O F MAC-ADDUCTS A N D O R I G I N O F ENANTIOSELECTION 124
REFERENCES 126
6 RECENT ADVANCES IN T H E SYNTHESIS A N D CATALYTIC HYDROGENATION O F
DEHYDROAMINO ACID DERIVATIVES A N D BICYCLO[2.2.2]OCTENES 131 VERONIQUE
MICHELET, VIRGINIE RATOVELOMANANA-VIDAL, VASILE I. PARVULESCU, AND
MARIJAN KOCEVAR 6.1 INTRODUCTION 131
6.2 SYNTHESIS O F DDAA DERIVATIVES A N D BICYCLO[2.2.2]OCTENES 133 6.3
LIGANDS 133
6.4 H O M O G E N E O U S H Y D R O G E N A T I O N A N D HYDROGENOLYSIS
REACTIONS W I T H
D E H Y D R O A M I N O ACID DERIVATIVES A N D BICYCLO[2.2.2]OCT-7-ENES
OVER NANOCOLLOIDS-MODIFIED CATALYSTS 136 6.4.1 N A N O M E T A L
COLLOIDS-MODIFIED CATALYSTS 136
6.4.2 NANOOXIDE COLLOIDS-MODIFIED CATALYSTS 140
6.5 H E T E R O G E N E O U S CATALYSTS FOR HYDROGENOLYSIS O F
BICYCLO[2.2.2]OCT-7-ENES 142 6.5.1 H E T E R O G E N E I Z E D
LIGAND-MODIFIED NANOCLUSTERS 142 6.6 LAYERED-DOUBLE HYDROXIDES AS A S U
P P O R T FOR RH(TPPTS)3 A N D
RH-(M-TPPTC)3 H O M O G E N E O U S CATALYSTS 144 6.7 CONCLUSIONS 147
A C K N O W L E D G M E N T S 147 REFERENCES 148
7 IR-CATALYZED HYDROGENATION O F MINIMALLY FUNCTIONALIZED OLEFINS USING
P H O S P H I T E - N I T R O G E N LIGANDS 153 MONTSERRAT DIEGUEZ, PHER
G. ANDERSSON, A N D OSCAR PAMIES 7.1 INTRODUCTION 153
7.2 APPLICATION O F P H O S P H I T E - N I T R O G E N LIGANDS 155
7.3 CONCLUSIONS 161
A C K N O W L E D G M E N T S 163 REFERENCES 163
IMAGE 4
V I I I C O N T E N T S
8 MODELING IN H O M O G E N E O U S CATALYSIS: A TUTORIAL 167
ERIC CLOT AND PER-OLA NORRBY 8.1 INTRODUCTION 167
8.2 MOLECULAR MODELING 167
8.3 WAVE F U N C T I O N THEORY, W F T 168
8.4 DENSITY FUNCTIONAL THEORY, D F T 369
8.5 ORBITALS 170
8.6 BASIS SETS 172
8.7 SOLVATION 174
8.8 ANALYZING T H E REACTION ENERGIES 175
8.9 ANALYZING T H E ELECTRONIC STRUCTURE 177
8.9.1 T H E NBO M E T H O D 178
8.9.1.1 H O W DOES IT WORK? 178
8.9.1.2 DEPARTURE F R O M T H E LEWIS STRUCTURE 180
8.9.1.3 NBO A N D TRANSITION METAL COMPLEXES 183
8.9.2 T H E AIM M E T H O D 187
8.9.2.1 H O W DOES IT WORK? 187
8.9.2.2 N A T U R E O F T H E B O N D E D INTERACTION 189
REFERENCES 190
PART III C - C A N D C - H E T E R O BOND-FORMING REACTIONS 193
9 GOLDEN TIMES FOR ALLENES 195
NORBERT KRAUSE
9.1 INTRODUCTION 195
9.2 CYCLIZATION O F HYDROXYALLENES 196
9.3 CYCLIZATION O F AMINOALLENES 203
9.4 CYCLIZATION O F THIOALLENES 206
9.5 CONCLUSION 206
REFERENCES 207
10 COPPER CATALYSIS IN ARENE A N D HETEROARENE FUNCTIONALIZATION T H R O
U G H
C - H BOND ACTIVATION 211 SANDRO CACCHI, GIANCARLO FABRIZI, A N D
ANTONELLA GOGGIAMANI 10.1 INTRODUCTION 211
10.2 C - C B O N D - F O R M I N G REACTIONS 212
10.2.1 VIA (HETERO)ARYL-H/R-X C O U P L I N G 212
10.2.1.1 R - X = (HETERO)ARYL HALIDES 2 1 2
10.2.1.2 R - X = ALKENYL BROMIDES 215
10.2.1.3 R - X = B R C H 2 A R 216
10.2.2 VIA (HETERO)ARYL-H/AR 2I +X~ COUPLING 217
10.2.2.1 DIRECT (HETERO)ARYLATION O F H E T E R O A R E N E S 217
10.2.2.2 DIRECT ARYLATION O F ARENES 218
10.2.3 VIA ( H E T E R O ) A R Y L - H / C - H COUPLING 219
10.2.3.1 DIMERIZATION O F (HETERO)ARENES 219
IMAGE 5
CONTENTS IX
10.2.3.2 CYCLIZATION O F ANILIDES 220
10.2.3.3 CYCLIZATION O F N-ARYL P-ENAMINONES 221 10.2.4 VIA ARYL-H
ADDITION TO T E R M I N A L ALKYNES 223
10.3 C - N B O N D - F O R M I N G REACTIONS 223
10.4 C - O B O N D - F O R M I N G REACTIONS 227
10.5 C - H A L O G E N B O N D - F O R M I N G REACTIONS 2 2 9
REFERENCES 230
11 LIGATED ORGANOCUPRATES: A N A - Z ROUTEMAP O F MECHANISM A N D
APPLICATION 233 S I M O N WOODWARD A N D DARREN WILLCOX 11.1 I N T R O D
U C T I O N 233
11.2 ACCEPTED MECHANISTIC PROPOSALS 233
11.2.1 KINETIC A N D N M R STUDIES 2 3 5
11.2.2 C O M P U T A T I O N A L STUDIES 242
11.2.3 N O N L I N E A R EFFECTS 243
11.2.4 CHALLENGES 2 4 5
11.3 SELECTIVE APPLICATIONS I N PRIVILEGED COPPER(I) CATALYSIS 2 4 5
11.3.1 CONJUGATE ADDITION 2 4 5
11.3.2 ADDITIONS TO ALLYLIC HALIDES 2 5 0
REFERENCES 2 5 2
12 RH-, AG-, A N D CU-CATALYZED C - N BOND FORMATION 2 5 7
PHILIPPE DAUBAN, CAMILLE LESCOT, M . M A R DIAZ-REQUEJO, AND
PEDRO J. PEREZ
12.1 INTRODUCTION 2 5 7
12.2 HISTORICAL BACKGROUND 2 5 8
12.3 COPPER- A N D SILVER-CATALYZED C - N B O N D F O R M A T I O N 2 6
0
12.4 RHODIUM-CATALYZED C - N B O N D F O R M A T I O N 2 6 5
12.5 CONCLUSIONS 273
REFERENCES 274
13 DEVELOPMENT O F T H E ASYMMETRIC N O Z A K I - H I Y A M A - K I S H
I REACTION 279
GRAINNE C. HARGADEN A N D PATRICK J. GUIRY 13.1 INTRODUCTION 279
13.2 DEVELOPMENT O F A CATALYTIC N O Z A K I - H I Y A M A - K I S H I
REACTION 2 7 9
13.3 CATALYTIC ENANTIOSELECTIVE N O Z A K I - H I Y A M A - K I S H I
REACTION 281
13.4 APPLICATION O F SALEN-DERIVED LIGANDS I N T H E ENANTIOSELECTIVE N
O Z A K I - H I Y A M A - K I S H I REACTION 283 13.5 APPLICATION O F
OXAZOLINE-CONTAINING LIGANDS I N T H E CATALYTIC ENANTIOSELECTIVE N O Z
A K I - H I Y A M A - K I S H I REACTION 286 13.6 APPLICATION O F T E T
H E R E D BIS(8-QUINOLINATO) C H R O M I U M COMPLEXES I N
T H E CATALYTIC ENANTIOSELECTIVE N O Z A K I - H I Y A M A - K I S H I
299 13.7 APPLICATION O F CHIRAL SPIROCYCLIC BORATE LIGANDS TO T H E
CATALYTIC ENANTIOSELECTIVE N O Z A K I - H I Y A M A - K I S H I
ALLYLATION 303
IMAGE 6
X I C O N T E N T S
13.8 APPLICATIONS O F CATALYTIC N O Z A K I - H I Y A M A - K I S H I
REACTION I N TOTAL
SYNTHESIS 303
13.9 CONCLUSIONS 3 0 5
REFERENCES 306
14 CHIRAL IMIDATE LIGANDS: SYNTHESIS A N D APPLICATIONS IN ASYMMETRIC
CATALYSIS 309
TIMOTHY NOEL, KATRIEN BERT, PIETER JANSSENS, A N D J O H A N VAN DER
EYCKEN 14.1 INTRODUCTION 309
14.2 CYCLIC IMIDATES 311
14.3 SYNTHESIS O F IMIDATES 3 1 2
14.4 SYNTHESIS O F I M I D A T E LIGANDS 313
14.5 SYNTHESIS O F I M I D A T E - C O P P E R (I) COMPLEXES 313
14.6 APPLICATION O F CHIRAL I M I D A T E LIGANDS I N ENANTIOSELECTIVE
CATALYSIS 315 '
14.6.1 C O P P E R (I)-CATALYZED A S Y M M E T R I C AZIRIDINATION 315
14.6.2 A S Y M M E T R I C DIETHYLZINC ADDITION 316
14.6.3 A S Y M M E T R I C PALLADIUM(0)-CATALYZED ALLYLIC ALKYLATIONS
316 14.6.4 A S Y M M E T R I C I R I D I U M (I)-CATALYZED
HYDROGENATIONS 318 14.7 NOVEL SYNTHETIC APPLICATIONS O F CYCLIC IMIDATES
320
14.7.1 ONE-STEP SYNTHESIS O F CHIRAL OXAZOLINE-ALCOHOL LIGANDS 320
14.7.2 SYNTHESIS O F CHIRAL SPIRO-2-ALKOXY-IMIDAZOLIDINES 321 14.8
CONCLUSIONS 3 2 2
REFERENCES 3 2 4
15 CATALYZED ORGANIC REACTIONS IN BALL MILLS 327
A C H I M STOLLE, BERND ONDRUSCHKA, A N K E KREBS, A N D CARSTEN BOLM
15.1 INTRODUCTION 327
15.2 ACID- O R BASE-CATALYZED REACTIONS 328
15.3 ORGANOCATALYTIC M E T H O D S 333
15.3.1 A S Y M M E T R I C ALDOL REACTIONS 333
15.3.2 CYCLOADDITION A N D RELATED REACTIONS 335
15.4 METAL-CATALYZED REACTIONS 338
15.4.1 S U Z U K I - M I Y A U R A REACTION 338
15.4.2 M I Z O R O K I - H E C K REACTION 3 4 0
15.4.3 SONOGASHIRA REACTION 341
15.4.4 CU-CATALYZED REACTIONS 343
15.4.5 MISCELLANEOUS METAL-CATALYZED REACTIONS 3 4 5 15.5 CONCLUSION A N
D PERSPECTIVE 347
REFERENCES 348
INDEX 351 |
| any_adam_object | 1 |
| author2 | Andersson, Pher 1963- |
| author2_role | edt |
| author2_variant | p a pa |
| author_GND | (DE-588)131923455 |
| author_facet | Andersson, Pher 1963- |
| building | Verbundindex |
| bvnumber | BV040147607 |
| classification_rvk | VK 5500 VK 5550 |
| classification_tum | CHE 621f CHE 167f |
| ctrlnum | (OCoLC)794530355 (DE-599)DNB1016558597 |
| dewey-full | 540 547.215 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 540 - Chemistry and allied sciences 547 - Organic chemistry |
| dewey-raw | 540 547.215 |
| dewey-search | 540 547.215 |
| dewey-sort | 3540 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Physik Chemie |
| format | Book |
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| id | DE-604.BV040147607 |
| illustrated | Illustrated |
| indexdate | 2024-12-05T09:00:48Z |
| institution | BVB |
| isbn | 3527330976 9783527330973 9783527646586 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-025004390 |
| oclc_num | 794530355 |
| open_access_boolean | |
| owner | DE-91G DE-BY-TUM DE-11 DE-703 DE-29T DE-19 DE-BY-UBM DE-92 |
| owner_facet | DE-91G DE-BY-TUM DE-11 DE-703 DE-29T DE-19 DE-BY-UBM DE-92 |
| physical | XVIII, 356 S. graph. Darst. |
| publishDate | 2012 |
| publishDateSearch | 2012 |
| publishDateSort | 2012 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Innovative catalysis in organic synthesis oxidation, hydrogenation, and C-X bond forming reactions ed. by Pher G. Andersson Weinheim Wiley-VCH 2012 XVIII, 356 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Literaturangaben Katalyse (DE-588)4029921-1 gnd rswk-swf Organische Synthese (DE-588)4075695-6 gnd rswk-swf Kupplungsreaktion (DE-588)4166199-0 gnd rswk-swf Organische Synthese (DE-588)4075695-6 s Kupplungsreaktion (DE-588)4166199-0 s Katalyse (DE-588)4029921-1 s DE-604 Andersson, Pher 1963- (DE-588)131923455 edt Erscheint auch als Online-Ausgabe, EPUB 978-3-527-64660-9 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-64659-3 Erscheint auch als Online-Ausgabe, PDF 978-3-527-64661-6 text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3902531&prov=M&dok_var=1&dok_ext=htm Inhaltstext DE-601 pdf/application http://www.gbv.de/dms/tib-ub-hannover/671469843.pdf Inhaltsverzeichnis DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025004390&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Innovative catalysis in organic synthesis oxidation, hydrogenation, and C-X bond forming reactions Katalyse (DE-588)4029921-1 gnd Organische Synthese (DE-588)4075695-6 gnd Kupplungsreaktion (DE-588)4166199-0 gnd |
| subject_GND | (DE-588)4029921-1 (DE-588)4075695-6 (DE-588)4166199-0 |
| title | Innovative catalysis in organic synthesis oxidation, hydrogenation, and C-X bond forming reactions |
| title_auth | Innovative catalysis in organic synthesis oxidation, hydrogenation, and C-X bond forming reactions |
| title_exact_search | Innovative catalysis in organic synthesis oxidation, hydrogenation, and C-X bond forming reactions |
| title_full | Innovative catalysis in organic synthesis oxidation, hydrogenation, and C-X bond forming reactions ed. by Pher G. Andersson |
| title_fullStr | Innovative catalysis in organic synthesis oxidation, hydrogenation, and C-X bond forming reactions ed. by Pher G. Andersson |
| title_full_unstemmed | Innovative catalysis in organic synthesis oxidation, hydrogenation, and C-X bond forming reactions ed. by Pher G. Andersson |
| title_short | Innovative catalysis in organic synthesis |
| title_sort | innovative catalysis in organic synthesis oxidation hydrogenation and c x bond forming reactions |
| title_sub | oxidation, hydrogenation, and C-X bond forming reactions |
| topic | Katalyse (DE-588)4029921-1 gnd Organische Synthese (DE-588)4075695-6 gnd Kupplungsreaktion (DE-588)4166199-0 gnd |
| topic_facet | Katalyse Organische Synthese Kupplungsreaktion |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=3902531&prov=M&dok_var=1&dok_ext=htm http://www.gbv.de/dms/tib-ub-hannover/671469843.pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025004390&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT anderssonpher innovativecatalysisinorganicsynthesisoxidationhydrogenationandcxbondformingreactions |