Anion-binding catalysis

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Weitere Verfasser: García Mancheño, Olga (HerausgeberIn)
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Veröffentlicht: Weinheim Wiley-VCH [2022]
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Datensatz im Suchindex

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adam_text CONTENTS PREFACE XI LIST OF ABBREVIATIONS XIII 1 FROM ANION RECOGNITION TO ORGANOCATALYTIC CHEMICAL REACTIONS 1 FRIEDEMANN DRESSIER AND PETER R. SCHREINER 1.1 INTRODUCTION AND BACKGROUND 1 1.1.1 EVOLUTION OF THIOUREA-BASED CATALYSTS 10 1.1.2 EVOLUTION OF TRIAZOLE-BASED CATALYSTS 22 1.1.3 PROGRESS ON HALOGEN-BINDING-BASED CATALYSTS 25 1.1.4 MISCELLANEOUS ANION-BINDING CATALYSTS 26 1.2 CONCEPTS IN ANION-BINDING CATALYSIS 31 1.2.1 INTRODUCTION 31 1.2.2 ANION-BINDING CATALYSIS IN ADDITION REACTIONS 36 1.2.3 ANION-BINDING CATALYSIS IN SUBSTITUTION REACTIONS 44 1.2.4 ANION BINDING IN COOPERATIVE CATALYSIS 54 1.2.5 ANION-BINDING IN LEWIS ACID ENHANCEMENT CATALYSIS 57 1.2.6 ANION-BINDING IN PHASE TRANSFER CATALYSIS 59 1.3 SUMMARY AND OUTLOOK 62 ACKNOWLEDGMENT 63 REFERENCES 64 2 ANION RECOGNITION AND BINDING CONSTANT DETERMINATION 79 EDWARD G. SHEETZ, DAVID VAN CRAEN, AND AMAR H. FLOOD 2.1 INTRODUCTION TO SUPRAMOLECULAR CHEMISTRY AND BINDING CONSTANT DETERMINATION 79 2.1.1 CHAPTER OVERVIEW 79 2.1.2 SUPRAMOLECULAR CHEMISTRY AND ITS CONNECTION TO ANION-ASSISTED CATALYSIS 80 2.1.3 BRIEF HISTORY OF ADVANCES IN SUPRAMOLECULAR ANION BINDING 84 2.1.4 PREDICTING THE MODEL OF ASSOCIATION AND SIMULATING THE EXPECTED SPECIES DISTRIBUTION PROFILES AND BINDING CURVES 86 VI CONTENTS 2.2 EQUILIBRIUM CONSTANTS, BINDING CURVES, TITRATION CONDITIONS, AND ERRORS 87 2.2.1 PHYSICAL ORIGINS OF EQUILIBRIUM BINDING CONSTANTS 87 2.2.2 EXPLANATION OF THE BASIS FOR TITRATION TECHNIQUES AND BINDING CURVES 88 2.2.3 HIROSE S RULE AND PICKING THE RIGHT CONCENTRATION, SOLVENT, AND TECHNIQUE 89 2.2.4 ERROR DETERMINATION 92 2.3 EXPERIMENTAL TECHNIQUES: NMR SPECTROSCOPY 92 2.3.1 WHEN TO USE 92 2.3.2 SLOW EXCHANGE VS. FAST EXCHANGE 93 2.3.3 DETERMINATION OF THE UNDERLYING EQUILIBRIA 94 2.3.4 SOFTWARE FOR NON-LINEAR REGRESSION FITTING 95 2.3.5 COMMON ISSUES 97 2.4 EXPERIMENTAL TECHNIQUES: UV-VIS SPECTROSCOPY 97 2.4.1 WHEN TO USE 97 2.4.2 PHYSICAL ORIGINS OF OPTICAL PHENOMENA 97 2.4.3 SOFTWARE FOR NON-LINEAR REGRESSION ANALYSIS OF UV-VIS TITRATIONS 98 2.4.4 COMMON ISSUES 99 2.5 UNDERAPPRECIATED CONCERNS IN BINDING CONSTANT DETERMINATION: MULTIPLE BINDING EQUILIBRIA 99 2.5.1 WHEN TO EXPECT ADDITIONAL EQUILIBRIA 99 2.5.2 HOW TO DIAGNOSE ADDITIONAL EQUILIBRIA 100 2.5.3 HOW TO ACCOUNT FOR ADDITIONAL EQUILIBRIA 101 2.6 UNDERAPPRECIATED CONCERNS IN BINDING CONSTANT DETERMINATION: ION PAIRING 102 2.6.1 WHEN TO EXPECT ION PAIRING 102 2.6.2 ROLE OF SOLVENT AND CONCENTRATION IN ION PAIRING 103 2.6.3 HOW TO DIAGNOSE ION PAIRING 103 2.7 UNDERAPPRECIATED CONCERNS IN BINDING CONSTANT DETERMINATION: KINETIC PROCESSES 104 2.8 CONNECTING EQUILIBRIUM CONSTANTS TO STRUCTURES AND CATALYSIS 104 2.9 CONCLUSION 105 ACKNOWLEDGMENT 105 REFERENCES 105 3 (THIO)UREA AND SQUARAMIDE-CATALYZED ANION-BINDING CATALYSIS WITH HALOGEN ANIONS 111 MATTHEW A. HORWITZ AND VERONIQUE GOUVERNEUR 3.1 INTRODUCTION 111 3.2 HISTORY AND BACKGROUND 111 3.3 ASYMMETRIC CATALYSIS BY CATALYST ASSOCIATION WITH THE ELECTROPHILE 113 3.3.1 EXAMPLES UTILIZING THE N-ACYLIMINIUM CHLORIDE ION PAIR 113 3.3.1.1 PICTET-SPENGLER REACTION AND VARIANTS 113 CONTENTS VII 3.3.1.2 INTRAMOLECULAR CYCLIZATIONS WITH OTHER (HETERO)AROMATIC NUCLEOPHILES 115 3.3.1.3 INTRAMOLECULAR AND INTERMOLECULAR AZA-SAKURAI REACTION 116 3.3.1.4 MANNICH REACTION AND VARIANTS 120 3.3.1.5 PETASIS-TYPE REACTIONS 121 3.3.2 EXAMPLES UTILIZING ELECTROPHILES OTHER THAN N-ACYLIMINIUM ION PRECURSORS 123 3.3.2.1 UTILIZATION OF OXOCARBENIUM AND PYRONE INTERMEDIATES 123 3.3.2.2 GLYCOSYLATION REACTIONS UTILIZING HBD-HALIDE BINDING 126 3.3.2.3 UTILIZATION OF NON-HETEROATOM-STABILIZED CARBOCATIONS AS ELECTROPHILES 127 3.4 ASYMMETRIC CATALYSIS BY CATALYST ASSOCIATION WITH THE NUCLEOPHILE 129 3.4.1 CATALYST-NUCLEOPHILE ASSOCIATION IN PHASE-TRANSFER CATALYSIS 130 3.4.1.1 INVESTIGATION OF HYDROGEN-BONDED FLUORIDE: STRUCTURE AND REACTIVITY 130 3.4.1.2 DEVELOPMENT OF HYDROGEN-BONDING PHASE-TRANSFER CATALYSIS (HBPTC) 130 3.4.1.3 DEVELOPMENT OF ACYL-TRANSFER CATALYSIS WITH HYDROGEN-BONDED FLUORIDE 134 3.4.2 CATALYST-NUCLEOPHILE ASSOCIATION IN HOMOGENEOUS CATALYSIS 135 3.5 CONCLUSIONS AND OUTLOOK 136 ACKNOWLEDGMENTS 137 REFERENCES 137 4 CHIRAL UREAS, THIOUREAS, AND SQUARAMIDES IN ANION-BINDING CATALYSIS WITH CO-CATALYTIC BRONSTED/LEWIS ACIDS 141 ADAM TROTTA AND ERIC N. LACOBSEN 4.1 INTRODUCTION 141 4.2 CARBOXYLIC ACID CO-CATALYSTS 141 4.3 SULFONIC ACID CO-CATALYSTS 148 4.4 MINERAL ACID CO-CATALYSTS 152 4.5 LEWIS ACID CO-CATALYSTS 155 4.6 CONCLUSIONS AND OUTLOOK 157 REFERENCES 157 5 ANION-BINDING CATALYSIS WITH OTHER ANIONS 161 SANKASH MITRA AND SANTANU MUKHERJEE 5.1 INTRODUCTION 161 5.2 CYANIDE ANION 162 5.2.1 STRECKER REACTION 163 5.2.2 ACYLCYANATION OF IMINES 168 5.3 OXYGEN-BASED ANIONS 169 5.3.1 ALKOXIDES AND ENOLATES 169 5.3.2 ENOLATES OF LACTONES, CYCLIC ANHYDRIDES, AND IMIDES 174 5.3.3 CARBOXYLATES 182 VIII I CONTENTS 5.4 CONCLUSIONS AND OUTLOOK 192 REFERENCES 193 6 SILANEDIOLS, PHOSPHORAMIDES, AND OTHER OH AND NH-BASED H-DONOR CATALYSTS 207 ALEXANDRIA LEVEILLE AND ANITA MATTSON 6.1 INTRODUCTION 201 6.2 SILANEDIOLS 201 6.2.1 INTRODUCTION 207 6.2.2 OVERVIEW OF SILANOLS IN ANION BINDING AND CATALYSIS 202 6.2.3 SILANEDIOL ANION-BINDING CATALYSIS 203 6.2.4 ALKOXYSILANEDIOL ANION BINDING CATALYSIS 207 6.3 SILOXANES 208 6.4 THIOPHOSPHORAMIDES 270 6.5 CYCLODIPHOSPHAZANES 213 6.6 OTHER EXAMPLES 275 6.6.1 XANTHENE-DIAMINE SCAFFOLD 275 6.6.2 CROCONAMIDES 276 6.6.3 PYRROLE-BASED ANION-BINDING CATALYST 277 6.6.4 BISAMIDINE CATALYSTS 277 6.7 CONCLUSIONS 218 REFERENCES 218 1 1,2,3-TRIAZOLES AND 1,2,3-TRIAZOLIUM IONS AS CATALYSTS 227 KOHSUKE OHMATSU AND TAKASHI OOI 7.1 INTRODUCTION 221 7.2 TRIAZOLE-BASED ANION-BINDING MOLECULAR CATALYSTS 224 7.3 TRIAZOLIUM IONS AS ORGANIC MOLECULAR CATALYSTS WITH ANION-BINDING ABILITY 231 7 A TRIAZOLIUM IONS IN DUAL FUNCTIONAL CATALYSTS 240 7.5 CONCLUSION 241 REFERENCES 242 8 QUATERNARY AMMONIUM, PHOSPHONIUM, AND TERTIARY SULFONIUM SALTS AS HYDROGEN-BONDING CATALYSTS 249 SEIJI SHIRAKAWA 8.1 INTRODUCTION 249 8.2 HYDROGEN-BONDING ABILITY OF QUATERNARY AMMONIUM SALTS 249 8.3 HYDROGEN-BONDING CATALYSIS OF QUATERNARY AMMONIUM SALTS 257 8.4 HYDROGEN-BONDING CATALYSIS OF QUATERNARY PHOSPHONIUM SALTS 257 8.5 HYDROGEN-BONDING CATALYSIS OF TERTIARY SULFONIUM SALTS 260 8.6 CONCLUSION 264 REFERENCES 264 CONTENTS IX 9 ASSISTED AND DUAL ANION BINDING IN AMINO AND NUCLEOPHILIC CATALYSIS 271 EFRAIM REYES, QUI-NHI DUONG, LIHER PRIETO, OLGA GARCIA MANCHENO, AND JOSE L. VICARIO 9.1 DUAL AMINO/H-BOND DONOR CATALYSIS 271 9.1.1 ENAMINE ACTIVATION 272 9.1.2 DIENAMINE ACTIVATION 276 9.1.3 IMINIUM ION ACTIVATION 278 9.1.4 VINYLOGOUS IMINIUM ION ACTIVATION 283 9.2 THIOUREA - PYRIDINE-BASED NUCLEOPHILIC DUAL CATALYSIS 284 9.2.1 KINETIC RESOLUTION AND DESYMMETRIZATION OF AMINES 284 9.2.2 ASYMMETRIC STEGLICH REARRANGEMENT 290 9.2.3 OTHER ACYLATION REACTIONS 296 9.2.4 ANION-BINDING-ASSISTED POLYMERIZATION REACTIONS 296 9.3 CONCLUSIONS 298 REFERENCES 299 10 ANION-BINDING CATALYSIS BY HALOGEN, CHALCOGEN, PNICTOGEN, AND TETREL BONDING 307 RAFFAELLA PAPAGNA, LUKAS VOGEL, AND STEFAN M. HUBER 10.1 HISTORY OF HALOGEN BONDING 307 10.2 HISTORY OF CHALCOGEN BONDING 310 10.3 HISTORY OF PNICTOGEN AND TETREL BONDING 314 10.4 DIFFERENCES BETWEEN HYDROGEN BONDING AND OTHER SECONDARY INTERACTIONS 315 10.5 SECONDARY BONDING IN ANION RECOGNITION 316 10.6 HALOGEN BONDING IN ANION-BINDING CATALYSIS 322 10.7 CHALCOGEN BONDING IN ANION-BINDING CATALYSIS 328 10.8 PNICTOGEN AND TETREL BONDING IN ANION-BINDING CATALYSIS 331 10.9 CONCLUSION 333 REFERENCES 334 11 NEW TRENDS AND SUPRAMOLECULAR APPROACHES IN ANION-BINDING CATALYSIS 345 MARIA C. PEREZ-AGUILAR, MELANIA GOMEZ-MARTINEZ, JAN KUHLMANN, AND OLGA GARCIA MANCHENO 11.1 GENERAL INTRODUCTION 345 11.2 DUAL PHOTOREDOX AND ANION-BINDING CATALYSIS 345 11.3 COMBINATION OF METAL AND ANION-BINDING CATALYSIS 351 11.3.1 ANION-BINDING ASSISTED HYDROGENATION REACTIONS 351 11.3.2 HYDROFORMYLATION REACTIONS 355 11.3.3 ANION-BINDING - METAL-CATALYZED C-C FORMING REACTIONS 358 11.4 SUPRAMOLECULAR APPROACHES INVOLVING ANION-BINDING CATALYSIS 359 X CONTENTS 11.4.1 MECHANICALLY INTERLOCKED MOLECULES IN ANION-BINDING CATALYSIS 359 11.4.1.1 MOLECULAR KNOTS AS ANION-BINDING CATALYSTS 360 11.4.1.2 ROTAXANES AS ANION-BINDING CATALYSTS 363 11.4.2 MOLECULAR MOTORS IN ANION-BINDING CATALYSIS 364 11.4.3 MACROCYCLES IN ANION-BINDING CATALYSIS 365 11.5 ANION-JT CATALYSIS 368 11.5.1 ANION-%-CATALYZED KEMP ELIMINATION REACTION 369 11.5.2 ANION-IT INTERACTIONS IN ENOLATE CHEMISTRY 370 11.5.3 EPOXIDE-OPENING - ETHER CYCLIZATION REACTIONS 372 11.5.4 ENANTIOSELECTIVE ANION-:: CATALYSIS 373 11.5.5 MISCELLANEOUS 376 11.6 CONCLUSION AND OUTLOOK 376 REFERENCES 377 INDEX 387
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author2 García Mancheño, Olga
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author_facet García Mancheño, Olga
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genre (DE-588)4143413-4 Aufsatzsammlung gnd-content
genre_facet Aufsatzsammlung
id DE-604.BV047567674
illustrated Illustrated
indexdate 2025-02-03T15:58:23Z
institution BVB
institution_GND (DE-588)16179388-5
isbn 9783527348572
3527348573
language English
oai_aleph_id oai:aleph.bib-bvb.de:BVB01-032953357
oclc_num 1298749555
open_access_boolean
owner DE-11
DE-19
DE-BY-UBM
DE-703
owner_facet DE-11
DE-19
DE-BY-UBM
DE-703
physical xvi, 397 Seiten Illustrationen, Diagramme
publishDate 2022
publishDateSearch 2022
publishDateSort 2022
publisher Wiley-VCH
record_format marc
spellingShingle Anion-binding catalysis
Katalyse (DE-588)4029921-1 gnd
Aktivierung Chemie (DE-588)4141761-6 gnd
Anion (DE-588)4130938-8 gnd
Organokatalyse (DE-588)7636906-7 gnd
subject_GND (DE-588)4029921-1
(DE-588)4141761-6
(DE-588)4130938-8
(DE-588)7636906-7
(DE-588)4143413-4
title Anion-binding catalysis
title_auth Anion-binding catalysis
title_exact_search Anion-binding catalysis
title_full Anion-binding catalysis edited by Olga García Mancheño
title_fullStr Anion-binding catalysis edited by Olga García Mancheño
title_full_unstemmed Anion-binding catalysis edited by Olga García Mancheño
title_short Anion-binding catalysis
title_sort anion binding catalysis
topic Katalyse (DE-588)4029921-1 gnd
Aktivierung Chemie (DE-588)4141761-6 gnd
Anion (DE-588)4130938-8 gnd
Organokatalyse (DE-588)7636906-7 gnd
topic_facet Katalyse
Aktivierung Chemie
Anion
Organokatalyse
Aufsatzsammlung
url http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-34857-2/
http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=032953357&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA
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