The organometallic chemistry of N-heterocyclic carbenes:
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Elektronisch E-Book |
| Sprache: | English |
| Veröffentlicht: |
Hoboken, NJ
Wiley
2017
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| Schriftenreihe: | Inorganic chemistry
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| Schlagworte: | |
| Online-Zugang: | FRO01 UBG01 UBR01 Volltext Inhaltsverzeichnis |
| Beschreibung: | Includes bibliographical references and index |
| Beschreibung: | 1 Online-Ressource (xiv, 334 Seiten) Illustrationen, Diagramme |
| ISBN: | 9781118698808 9781118698785 |
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Datensatz im Suchindex
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| adam_text | Titel: The organometallic chemistry of N-heterocyclic carbenes
Autor: Huynh, Han-Vinh
Jahr: 2017
The Organometallic Chemistry of N-heterocyclic Carbenes Hän Vinh Huynh Department of Chemistry National University of Singapore Republic of Singapore Wiley
Contents Foreword ..................................................ix Preface ....................................................x List of Abbreviations and Definitions...................... xii 1 General Introduction.................................. 1 1.1 Definition of Carbenes.......................................1 1.2 Historical Overview of Carbenes, N-Heterocyclic Carbenes, and Their Complexes........................................3 1.2.1 The Quest for Free Stable Carbenes............................3 1.2.2 The Quest for Carbene Complexes............................11 References................................................15 2 General Properties of Classical NHCs and Their Complexes....................17 2.1 Stabilization in NHCs ( Push-Pull Effect) .............................19 2.2 Backbone Differences and Their Implications..........................20 2.3 Dimerization of Carbenes.....................................22 2.4 Nomenclature of N-Heterocyclic Carbenes............................25 2.5 Electronic Properties of NHCs and Different Electronic Parameters...............29 2.5.1 Tolman’s Electronic Parameter (TEP) and Related Carbonyl Based Systems......29 2.5.2 Lever’s Electronic Parameter (LEP)...........................36 2.5.3 Huynh’s Electronic Parameter (HEP)...........................38 2.6 Steric Properties of NHCs.....................................42 2.7 Structural Diversity of NHC Ligands and Their Complexes...................45 2.7.1 Donor-Functionalized NHCs...............................45 2.7.2 Multidentate NHCs....................................46 2.7.3 Pincer-Type NHC Ligands................................47 2.7.4 Tripodal and Macrocyclic Ligands............................48 References................................................49 3 Synthetic Aspects............................................52 3.1 General Routes to Azolium Salts as NHC
Precursors......................52 3.1.1 N-Alkylation of Neutral Azoles..............................52 3.1.2 Multicomponent Condensation Reactions........................55 3.1.3 Cyclization of Diamines...................... 58 3.1.4 Cyclization of Formamidines...............................64 3.2 General Routes to Free NHCs...................................66 3.2.1 NHCs via Deprotonation of Azolium Salts...... 68 3.2.2 NHCs via Reduction of Thiones.............................71 3.2.3 NHCs via a-Elimination of Small Molecules.......................73
vi Contents 3.3 General Synthetic Routes to NHC Complexes............ 74 3.3.1 Coordination of Free NHCs................................76 3.3.2 Cleavage of Electron-Rich Entetramines by Transition Metals..............78 3.3.3 In Situ Deprotonation of Azolium Salts in the Presence of Transition Metals......78 3.3.4 Carbene Transfer Routes.................................81 3.3.5 Oxidative Addition of an Azolium Salt to a Low-Valent Metal Complex........83 3.3.6 Metal-Template Synthesis Using Isocyanide Complexes as Precursors.........85 3.3.7 NHC Complexes by Small Molecule Elimination....................89 3.3.8 NHC Complexes by Protonation/Alkylation of Azolyl Complexes...........93 References................................................95 4 Group 10 Metal(0)-NHC Complexes.................................99 4.1 Nickel(0)-NHC Complexes....................................99 4.1.1 Reactions of Enetetramines and Free NHCs.......................99 4.1.2 Reduction of Nickel(II)-NHC Complexes.......................106 4.2 Palladium(0)-NHC Complexes.................................107 4.2.1 Reactions of Free NHCs................................107 4.2.2 Reduction of Palladium(H)-NHC Complexes......................112 4.3 Platinum(0)-NHC Complexes..................................115 4.3.1 Homoleptic Complexes.................................115 4.3.2 Heteroleptic Complexes.................................117 References...............................................120 5 Group 10 Metal(II)-NHC Complexes................................122 5.1 Nickel(II)-NHC Complexes...................................122 5.1.1 Cleavage of Enetetramines and the Free Carbene Route................122 5.1.2 In Situ Deprotonation of Azolium Salts with Basic Metal Salts............124 5.1.3 The Silver-Carbene Transfer Route...........................127 5.2 Palladium(II)-NHC Complexes................... 129 5.2.1 Cleavage of Entetramines and
the Free Carbene Route.................130 5.2.2 In Situ Deprotonation of Azolium Salts with External Base..............133 5.2.3 The “Palladium Acetate” Route.............................135 5.2.4 The Silver-Carbene Transfer Route...........................139 5.2.5 Isomers of Bis(NHC) Palladium(II) Complexes....................143 5.3 Platinum(II)-NHC Complexes.................................150 5.3.1 Cleavage of Entetramines................................151 5.3.2 Cyclization of Isocyanide Complexes..........................152 5.3.3 The Oxidative Addition Route.............................153 5.3.4 The Free Carbene Route................................157 5.3.5 In Situ Deprotonation of Azolium Salts with External Base..............159 5.3.6 In Situ Deprotonation with Basic Platinum Precursors.................162 5.3.7 Carbene Transfer Reactions...............................164 References...............................................168 6 Group 11 Metal-NHC Complexes.................................171 6.1 Copper(I)-NHC Complexes...................................171 6.1.1 The Free Carbene Route................................171 6.1.2 Alkylation of Copper-Azolate Complexes.......................172
Contents vii 6.1.3 In Situ Deprotonation with External Base.......................173 6.1.4 In Situ Deprotonation with Basic Copper Precursors.................. Ill 6.1.5 The Silver Carbene Transfer Route...........................180 6.1.6 The Copper Powder Route...............................182 6.2 Silver(I)-NHC Complexes...................................183 6.2.1 The Free Carbene Route................................183 6.2.2 In Situ Deprotonation with Basic Silver Precursors..................186 6.2.3 Silver-Carbene Transfer Reactions...........................192 6.3 Gold(I)-NHC Complexes....................................194 6.3.1 Cleavage of Enetetramines...............................194 6.3.2 Protonation/Alkylation of Azolato Complexes.....................194 6.3.3 The Free Carbene Route................................196 6.3.4 The Silver-Carbene Transfer Route...........................200 6.3.5 Ligand Redistribution and Autoionization of Gold® NHC Complexes........210 6.4 Gold(III)-NHC Complexes...................................212 References...............................................218 7 Ruthenium, Rhodium, and Iridium Metal-NHC Complexes...................220 7.1 Ruthenium(II)-NHC Complexes................................220 7.1.1 Cleavage of Enetetramines and the Free Carbene Route................220 7.1.2 In Situ a-Elimination..................................227 7.1.3 In Situ Deprotonation of Azolium Salts.........................228 7.1.4 The Silver-Carbene Transfer Route...........................230 7.2 Rhodium(I)- and Rhodium(III)-NHC Complexes.......................232 7.2.1 Cleavage of Enetetramines and the Free Carbene Route................232 7.2.2 In Situ Deprotonation of Azolium Salts.........................238 7.2.3 The Silver-Carbene Transfer Route...........................243 7.3 Iridium(I)- and Iridium(III) NHC Complexes.........................245 7.3.1 Cleavage of
Enetetramines and the Free Carbene Route................245 7.3.2 In Situ a-Elimination..................................250 7.3.3 In Situ Deprotonation of Azolium Salts.........................251 7.3.4 The Silver-Carbene Transfer Route...........................256 References...............................................261 8 Beyond Classical N-heterocyclic Carbenes I............................263 8.1 N,S-Heterocyclic Carbenes (NSHCs)..............................263 8.2 N,0-Heterocyclic Carbenes (NOHCs).............................270 8.3 Expanded Six-Membered NHCs................................277 8.4 Expanded Seven- and Eight-Membered NHCs.........................282 8.5 Expanded Diamidocarbenes (DAC)...............................287 References...............................................291 9 Beyond Classical N-heterocyclic Carbenes II...........................293 9.1 Abnormal Imidazolin-4/5-ylidenes (aNHC)..........................294 9.2 Mesoionic l,2,3-Triazolin-5-ylidenes (MIC)..........................303 9.3 Pyrazolin-3/5-ylidenes (Pyry) and Indazolin-3-ylidenes (Indy)................310 9.3.1 Pyrazolin-3/5-ylidenes.................................310 9.3.2 Indazolin-3-ylidenes..................................317
viii Contents 9.4 Cyclic (Alkyl)(Amino)Carbenes (CAACs) Or Pyrrolidin-2-ylidenes.............320 9.5 Remote N-Heterocyclic Carbenes (rNHC)............................324 9.5.1 Pyridin-3/4-ylidenes...................................324 9.5.2 Pyrazolin-4-ylidenes..................................326 References...............................................328 Index 330
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| spelling | Huynh, Han-Vinh 1972- Verfasser (DE-588)12395620X aut The organometallic chemistry of N-heterocyclic carbenes Han Vinh Huynh, Department of Chemistry, National University of Singapore Hoboken, NJ Wiley 2017 1 Online-Ressource (xiv, 334 Seiten) Illustrationen, Diagramme txt rdacontent c rdamedia cr rdacarrier Inorganic chemistry Includes bibliographical references and index Carbenes (Methylene compounds) fast Heterocyclic chemistry fast Organometallic chemistry fast SCIENCE / Chemistry / Organic bisacsh Chemie Organometallic chemistry Heterocyclic chemistry Carbenes (Methylene compounds) Heterocyclische Carbene -N (DE-588)7652572-7 gnd rswk-swf Metallorganische Verbindungen (DE-588)4038906-6 gnd rswk-swf Heterocyclische Carbene -N (DE-588)7652572-7 s Metallorganische Verbindungen (DE-588)4038906-6 s DE-604 Erscheint auch als Druck-Ausgabe 978-1-118-59377-6 https://onlinelibrary.wiley.com/doi/book/10.1002/9781118698785 Verlag URL des Erstveröffentlichers Volltext HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029448599&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Huynh, Han-Vinh 1972- The organometallic chemistry of N-heterocyclic carbenes Carbenes (Methylene compounds) fast Heterocyclic chemistry fast Organometallic chemistry fast SCIENCE / Chemistry / Organic bisacsh Chemie Organometallic chemistry Heterocyclic chemistry Carbenes (Methylene compounds) Heterocyclische Carbene -N (DE-588)7652572-7 gnd Metallorganische Verbindungen (DE-588)4038906-6 gnd |
| subject_GND | (DE-588)7652572-7 (DE-588)4038906-6 |
| title | The organometallic chemistry of N-heterocyclic carbenes |
| title_auth | The organometallic chemistry of N-heterocyclic carbenes |
| title_exact_search | The organometallic chemistry of N-heterocyclic carbenes |
| title_full | The organometallic chemistry of N-heterocyclic carbenes Han Vinh Huynh, Department of Chemistry, National University of Singapore |
| title_fullStr | The organometallic chemistry of N-heterocyclic carbenes Han Vinh Huynh, Department of Chemistry, National University of Singapore |
| title_full_unstemmed | The organometallic chemistry of N-heterocyclic carbenes Han Vinh Huynh, Department of Chemistry, National University of Singapore |
| title_short | The organometallic chemistry of N-heterocyclic carbenes |
| title_sort | the organometallic chemistry of n heterocyclic carbenes |
| topic | Carbenes (Methylene compounds) fast Heterocyclic chemistry fast Organometallic chemistry fast SCIENCE / Chemistry / Organic bisacsh Chemie Organometallic chemistry Heterocyclic chemistry Carbenes (Methylene compounds) Heterocyclische Carbene -N (DE-588)7652572-7 gnd Metallorganische Verbindungen (DE-588)4038906-6 gnd |
| topic_facet | Carbenes (Methylene compounds) Heterocyclic chemistry Organometallic chemistry SCIENCE / Chemistry / Organic Chemie Heterocyclische Carbene -N Metallorganische Verbindungen |
| url | https://onlinelibrary.wiley.com/doi/book/10.1002/9781118698785 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029448599&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT huynhhanvinh theorganometallicchemistryofnheterocycliccarbenes |