Pincer and pincer-type complexes: applications in organic synthesis and catalysis
Gespeichert in:
| Weitere Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Weinheim
Wiley-VCH
2014
|
| Schlagworte: | |
| Online-Zugang: | Inhaltstext Inhaltsverzeichnis |
| Beschreibung: | XV, 302 S. Ill., graph. Darst. |
| ISBN: | 9783527334421 9783527681303 |
Internformat
MARC
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Datensatz im Suchindex
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CONTENTS
PREFACE XI
LIST OF CONTRIBUTORS XIII
1 CATALYSIS BY PINCER COMPLEXES: SYNTHESIS OF ESTERS, AMIDES, AND
PEPTIDES 1
CHIDAMBARAM GUNANATHAN AND DAVID MILSTEIN
1.1 INTRODUCTION AND BACKGROUND 1
1.2 BOND ACTIVATION BY METAL-LIGAND COOPERATION 3
1.3 SYNTHESIS OF ESTERS 4
1.3.1 SYNTHESIS OF ESTERS FROM PRIMARY ALCOHOLS 4
1.3.2 SYNTHESIS OF CROSS-ESTERS FROM PRIMARY AND SECONDARY ALCOHOLS 9
1.3.3 SYNTHESIS OF ESTERS BY ACYLATION OF SECONDARY ALCOHOLS USING
ESTERS 9
1.3.4 SYNTHESIS OF POLYESTERS FROM DIOLS 11
1.4 SYNTHESIS OF AMIDES 15
1.4.1 SYNTHESIS OF AMIDES FROM ALCOHOLS AND AMINES 15
1.4.2 SYNTHESIS OF AMIDES FROM ESTERS AND AMINES 18
1.4.3 SYNTHESIS OF POLYAMIDES FROM DIOLS AND DIAMINES 20
1.5 SYNTHESIS OF PEPTIDES FROM P-AMINO ALCOHOLS 24
1.6 CONCLUDING REMARKS 26
ACKNOWLEDGMENTS 26
REFERENCES 27
2 THE ROLE OF REDOX PROCESSES IN REACTIONS CATALYZED BY NICKEL AND
PALLADIUM COMPLEXES WITH ANIONIC PINCER LIGANDS 31
JUAN CDMPORA AND CRISTDBAL MELERO
2.1 INTRODUCTION 31
2.2 PINCER COMPLEXES OF NI, PD, AND PT IN OXIDATION STATES DIFFERENT
FROM
II 34
2.2.1 COMPLEXES IN THE HIGHER OXIDATION STATES (III, IV) 34
2.2.2 REDUCED COMPLEXES OF NI, PD, AND PT WITH PINCER LIGANDS 43
2.3 CATALYTIC REACTIONS INVOLVING REDOX PROCESSES IN THE PINCER-METAL
FRAMEWORK 46
HTTP://D-NB.INFO/1047121204
VI I CONTENTS
2.3.1 ATOM-TRANSFER RADICAL ADDITION (ATRA) AND POLYMERIZATION
REACTIONS (ATRP) 46
2.3.2 THE HECK REACTION 48
2.3.3 C-C CROSS-COUPLING REACTIONS 54
2.3.4 CARBON - H ETEROATOM COUPLING REACTIONS 62
2.4 CONCLUDING REMARKS 65
ACKNOWLEDGMENT 66
REFERENCES 66
3 APPENDED FUNCTIONALITY, IN PINCER LIGANDS 71
CAMERON M. MOORE AND NATHANIEL K. SZYMCZAK
3.1 INTRODUCTION 71
3.1.1 DESIGN CRITERIA 72
3.1.2 MOTIVATIONS 72
3.1.2.1 TRANSITION-METAL CATALYSIS 72
3.1.2.2 SUPRAMOLECULAR ARCHITECTURES 73
3.2 APPENDED FUNCTIONALITY COPLANAR WITH THE PINCER CHELATE 75
3.2.1 SYSTEMS THAT INCORPORATE 2,2':6',2"-TERPYRIDINE 75
3.2.1.1 SYNTHETIC STRATEGIES 75
3.2.1.2 APPENDED LEWIS ACID/BASES 77
3.2.1.3 APPENDED HYDROGEN-BOND ACCEPTOR/DONORS 79
3.2.2 PYRIDINE-2,6-DICARBOXAMIDE SYSTEMS 84
3.3 APPENDED FUNCTIONALITY NOT COPLANAR TO THE PINCER CHELATE
86
3.3.1 ENE PINCER SYSTEMS 86
3.3.2 PCP PINCER SYSTEMS 88
3.3.3 PEP PINCER SYSTEMS 88
3.3.4 PYRIDINE-2,6-DIIMINE SYSTEMS 90
3.4 FUTURE OUTLOOK AND SUMMARY 91
REFERENCES 91
4 C-C,
C-O,
AND C-B BOND FORMATION BY PINCER COMPLEXES INCLUDING
ASYMMETRIC CATALYSIS 95
KDLMDN J. SZABO
4.1 INTRODUCTION - PROS AND CONS OF USING PINCER COMPLEXES IN
CATALYSIS 95
4.2 REACTION OF I MINES AND I SOCYANOACETATES 96
4.2.1 STEREOSELECTIVE SYNTHESIS OF IMIDAZOLINES 96
4.2.2 APPLICATION OF CHIRAL PINCER COMPLEXES 99
4.2.3 MECHANISTIC CONSIDERATIONS 101
4.3 C-H FUNCTIONALIZATION OF ORGANONITRILES 102
4.3.1 ALLYLATION OF IMINES 102
4.3.2 BENZYL AMINE SYNTHESIS 103
4.4 REACTIONS INVOLVING HYPERVALENT IODINES 107
4.4.1 ARYLATION OF ALKENES USING PINCER COMPLEX CATALYSIS 107
4.4.2 ACETOXYLATION WITH HYPERVALENT IODINES 109
CONTENTS IVII
4.4.3 C-H BORYLATION OF ALKENES 112
4.5 SUMMARY AND OUTLOOK 113
REFERENCES 115
5 NICKEL-CATALYZED CROSS-COUPLING REACTIONS 117
ANUBENDU ADHIKARY AND HAIRONG GUAN
5.1 INTRODUCTION 117
5.2 CARBON-CARBON BOND-FORMING REACTIONS 118
5.2.1 KUMADA-CORRIU-TAMAO COUPLING 118
5.2.2 SUZUKI-MIYAURA COUPLING 129
5.2.3 NEGISHI COUPLING 132
5.2.4 SONOGASHIRA COUPLING 139
5.2.5 MIZOROKI-HECK REACTION 140
5.2.6 OTHER MISCELLANEOUS CROSS-COUPLING REACTIONS 141
5.3 CARBON-HETEROATOM BOND-FORMING REACTIONS 143
5.4 SUMMARY AND OUTLOOK 144
ACKNOWLEDGMENTS 144
REFERENCES 144
6 PSIP TRANSITION-METAL PINCER COMPLEXES: SYNTHESIS, BOND ACTIVATION,
AND CATALYSIS 149
LAURA TURCULET
6.1 INTRODUCTION 149
6.2 PSIP LIGAND SYNTHESES 151
6.3 GROUP 8 METAL PSIP CHEMISTRY
6.4 GROUP 9 METAL PSIP CHEMISTRY
6.5 GROUP 10 METAL PSIP CHEMISTRY
6.6 GROUP 11 METAL PSIP CHEMISTRY
6.7 ALTERNATIVE SILYL PINCERS 180
6.8 SUMMARY 183
REFERENCES 183
7 ELECTRONIC STRUCTURES OF REDUCED MANGANESE, IRON, AND COBALT
COMPLEXES BEARING REDOX-ACTIVE BIS(IMINO)PYRIDINE PINCER
LIGANDS 189
PAUL J. CHIRIK
7.1 INTRODUCTION 189
7.2 REDUCED MANGANESE, IRON, AND COBALT COMPLEXES WITH REDOX-ACTIVE
BIS(IMINO)PYRIDINES 189
7.2.1 REDUCED BIS(IMINO)PYRIDINE MANGANESE CHEMISTRY 190
7.2.2 REDUCED BIS(IMINO)PYRIDINE IRON CHEMISTRY 193
7.2.3 REDUCED BIS(IMINO)PYRIDINE COBALT CHEMISTRY 200
7.3 CONCLUSIONS AND OUTLOOK 209
REFERENCES 209
153
161
169
179
VIII I CONTENTS
8 PINCER COMPLEXES WITH SATURATED FRAMEWORKS: SYNTHESIS AND
APPLICATIONS 213
KLARA J. JONASSON AND OLA F. WENDT
8.1 INTRODUCTION 213
8.2 SYNTHESIS OF THE LIGANDS 213
8.3 SYNTHESIS AND COORDINATION BEHAVIOR OF CARBOMETALLATED PC(SP
3
)P
COMPLEXES 215
8.3.1 COORDINATION FLEXIBILITY IN ACYCLIC PC(SP
3
)P COMPLEXES 216
8.4 REACTIVITY AND CATALYTIC APPLICATIONS OF PC(SP
3
)P COMPLEXES 217
8.4.1 AMMONIA ACTIVATION 217
8.4.2 ISOTOPIC LABELING 219
8.4.3 REACTIONS WITH COORDINATED OLEFINS 219
8.4.4 CARBON-CARBON COUPLING REACTIONS 221
8.4.5 HYDROGENATION AND DEHYDROGENATION 223
8.4.6 C0
2
ACTIVATION 225
REFERENCES 225
9 HEAVIER CROUP 14 ELEMENTS-BASED PINCER COMPLEXES IN CATALYTIC
SYNTHETIC TRANSFORMATIONS OF UNSATURATED HYDROCARBONS 229
JUN TAKAYA AND NOBUHARU IWASAWA
9.1 INTRODUCTION 229
9.2 SYNTHESIS OF PALLADIUM COMPLEXES BEARING PXP-PINCER LIGANDS
(X = SI, GE, SN) 230
9.2.1 SYNTHESIS 230
9.2.2 STRUCTURAL ANALYSES 230
9.3 HYDROCARBOXYLATION 231
9.3.1 HYDROCARBOXYLATION OF ALLENES 232
9.3.2 HYDROCARBOXYLATION OF 1,3-DIENES 234
9.4 REDUCTIVE ALDOL TYPE REACTION 235
9.5 DEHYDROGENATIVE BORYLATION 237
9.5.1 DEHYDROGENATIVE BORYLATION OF ALKENES AND 1,3-DIENES 237
9.5.2 MECHANISTIC CONSIDERATIONS 239
9.6 SYNTHESIS AND REACTION OF R|
2
-(SI*H)PD(O) COMPLEX AS AN EQUIVALENT
TO PSIP-PALLADIUM HYDRIDE COMPLEXES 241
9.6.1 SYNTHESIS AND STRUCTURE OF R|
2
-(SI*H)PD(O) 241
9.6.2 REACTION OF R|
2
-(SI*H)PD(O) COMPLEX WITH AN ALLENE 242
9.6.3 REACTION OF R|
2
-(SI*H)PD(O) COMPLEX WITH DIBORON 244
9.7 CONCLUSIONS 245
REFERENCES 246
10 EXPERIMENTAL AND THEORETICAL ASPECTS OF PALLADIUM PINCER-CATALYZED
C-C CROSS-COUPLING REACTIONS 249
CHRISTIAN M. FREEH
10.1 C-C CROSS-COUPLING REACTIONS - AN INDISPENSABLE TOOL FOR THE
SYNTHESIS OF COMPLEX ORGANIC MOLECULES 249
CONTENTS | IX
10.2 PALLADIUM PINCER COMPLEXES AS C-C CROSS-COUPLING CATALYSTS 250
10.3 THE ROLE OF PALLADIUM PINCER COMPLEXES IN HECK REACTIONS 253
10.3.1 PD"/PD
LV
CYCLES AND PALLADIUM NANOPARTICLE FORMATION 256
10.4 COMPUTATIONAL INVESTIGATIONS ON THE THERMAL FEASIBILITY OF PD"/PD
IV
CYCLES OF PALLADIUM PINCER-CATALYZED HECK REACTIONS 262
10.4.1 POSSIBLE INITIAL REACTION STEPS OF PD"/PD
LV
MECHANISMS 263
10.4.2 INVESTIGATIONS ON MECHANISMS INITIATED BY OXIDATIVE ADDITION OF
PHENYL BROMIDE ON THE PALLADIUM(LL) CENTER OF
[{C
6
H
3
-2,6-(NHP(PIPERIDINYL)
2
)
2
}PD(CL)] (10) 263
10.4.3 INVESTIGATIONS ON MECHANISMS INITIATED BY STYRENE COORDINATION
AND/OR CHLORIDE DISSOCIATION 265
10.4.4 PD
N
/PD
LV
CYCLE PROPOSED FOR PALLADIUM PINCER-CATALYZED HECK
REACTIONS 270
10.4.5 HECK REACTIONS CATALYZED BY PALLADIUM PINCER COMPLEXES: PD
L!
/PD
LV
CYCLES AND/OR PALLADIUM NANOPARTICLE FORMATION 274
10.5 THEORETICAL INVESTIGATIONS ON A PINCER-CATALYZED NEGISHI
CROSS-COUPLING REACTION 275
10.6 CONCLUDING REMARKS 277
REFERENCES 278
11 REACTIONS OF SQUARE-PLANAR D
8
PINCER COMPLEXES WITH OXYGEN AND
HYDROGEN 281
WILSON D. BAILEY, MARIE V. PARKES, RICHARD A. KEMP, AND KAREN I.
GOLDBERG
11.1 INTRODUCTION 281
11.2 INSERTION OF MOLECULAR OXYGEN INTO LATE-TRANSITION METAL HYDRIDE
BONDS 284
11.3 HYDROGENOLYSIS OF LATE-TRANSITION METAL HYDROXIDE AND ALKOXIDE
COMPLEXES 289
11.4 SUMMARY 294
ACKNOWLEDGMENT 294
REFERENCES 295
INDEX 299 |
| any_adam_object | 1 |
| author2 | Szabó, Kálmán J. |
| author2_role | edt |
| author2_variant | k j s kj kjs |
| author_GND | (DE-588)1054603812 |
| author_facet | Szabó, Kálmán J. |
| building | Verbundindex |
| bvnumber | BV041992138 |
| classification_rvk | VH 9600 VH 9700 VK 5560 VK 5800 |
| ctrlnum | (OCoLC)870543628 (DE-599)DNB1047121204 |
| 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 |
| format | Book |
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| genre | (DE-588)4143413-4 Aufsatzsammlung gnd-content |
| genre_facet | Aufsatzsammlung |
| id | DE-604.BV041992138 |
| illustrated | Illustrated |
| indexdate | 2024-11-15T11:02:03Z |
| institution | BVB |
| isbn | 9783527334421 9783527681303 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-027434348 |
| oclc_num | 870543628 |
| open_access_boolean | |
| owner | DE-188 DE-29T DE-11 DE-19 DE-BY-UBM |
| owner_facet | DE-188 DE-29T DE-11 DE-19 DE-BY-UBM |
| physical | XV, 302 S. Ill., graph. Darst. |
| publishDate | 2014 |
| publishDateSearch | 2014 |
| publishDateSort | 2014 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Pincer and pincer-type complexes applications in organic synthesis and catalysis ed. by Kálmán J. Szabó ... Weinheim Wiley-VCH 2014 XV, 302 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Organische Synthese (DE-588)4075695-6 gnd rswk-swf Pincer-Ligand (DE-588)1054667616 gnd rswk-swf Metallkomplexe (DE-588)4038898-0 gnd rswk-swf Katalysator (DE-588)4029919-3 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Metallkomplexe (DE-588)4038898-0 s Pincer-Ligand (DE-588)1054667616 s Katalysator (DE-588)4029919-3 s Organische Synthese (DE-588)4075695-6 s DE-604 Szabó, Kálmán J. (DE-588)1054603812 edt Erscheint auch als Online-Ausgabe, EPUB 978-3-527-68133-4 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-68131-0 Erscheint auch als Online-Ausgabe, PDF 978-3-527-68132-7 X:MVB text/html http://deposit.dnb.de/cgi-bin/dokserv?id=4583956&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=027434348&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Pincer and pincer-type complexes applications in organic synthesis and catalysis Organische Synthese (DE-588)4075695-6 gnd Pincer-Ligand (DE-588)1054667616 gnd Metallkomplexe (DE-588)4038898-0 gnd Katalysator (DE-588)4029919-3 gnd |
| subject_GND | (DE-588)4075695-6 (DE-588)1054667616 (DE-588)4038898-0 (DE-588)4029919-3 (DE-588)4143413-4 |
| title | Pincer and pincer-type complexes applications in organic synthesis and catalysis |
| title_auth | Pincer and pincer-type complexes applications in organic synthesis and catalysis |
| title_exact_search | Pincer and pincer-type complexes applications in organic synthesis and catalysis |
| title_full | Pincer and pincer-type complexes applications in organic synthesis and catalysis ed. by Kálmán J. Szabó ... |
| title_fullStr | Pincer and pincer-type complexes applications in organic synthesis and catalysis ed. by Kálmán J. Szabó ... |
| title_full_unstemmed | Pincer and pincer-type complexes applications in organic synthesis and catalysis ed. by Kálmán J. Szabó ... |
| title_short | Pincer and pincer-type complexes |
| title_sort | pincer and pincer type complexes applications in organic synthesis and catalysis |
| title_sub | applications in organic synthesis and catalysis |
| topic | Organische Synthese (DE-588)4075695-6 gnd Pincer-Ligand (DE-588)1054667616 gnd Metallkomplexe (DE-588)4038898-0 gnd Katalysator (DE-588)4029919-3 gnd |
| topic_facet | Organische Synthese Pincer-Ligand Metallkomplexe Katalysator Aufsatzsammlung |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=4583956&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=027434348&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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