Catalytic hydroarylation of carbon-carbon multiple bonds. (2017)

• Record Type: Book
• Further Information: Note: Edited by Lutz Ackermann, T. Brent Gunnoe, Laurel Goj Habgood.
• Editors: Ackermann, Lutz; Habgood, Laurel Goj; Gunnoe, T. Brent
• Contents: List of Contributors xi Introduction and Preface 1 Laurel G. Habgood, Lutz Ackermann, and T. Brent Gunnoe References 3 1 Functionalization of Heteroaromatic Substrates using Groups 9 and 10 Catalysts 5; Pedro Villuendas, Sara Ruiz, and Esteban P. Urriolabeitia 1.1 Introduction 5 1.2 Thiophenes, furans, and Related Heterocycles 8 1.3 Pyrroles, Indoles, Pyridines, and Imidazopyridines 21 1.4 Azoles and Other Miscellaneous Heterocycles 31 1.5 Summary 39 References 40 2 Ruthenium Catalysts for the Alkylation of Functionalized Arenes and Heteroaromatic Substrates via Hydroarylation 49; David J. Burns, Sergei I. Kozhushkov, and Lutz Ackermann 2.1 Introduction 49 2.2 Alkylation by Ruthenium(0) Catalysts via Oxidative-Addition C–H Activation 50 2.2.1 Alkylation by Ruthenium(II) Catalysts via Carboxylate-Assisted C–H Activation 63 2.3 Summary and Conclusions 70 Abbreviations 71 References 71 3 Alkylation of ArenesWithout Chelation Assistance: Transition Metal Catalysts with d6 Electron Configurations 83; Bradley A. McKeown, Laurel Goj Habgood, Thomas R. Cundari, and T. Brent Gunnoe 3.1 Transition Metal-Mediated Arene Alkylation: Overview 83 3.2 Octahedral d6 Transition Metal Catalysts for Olefin Hydroarylation: Scorpionate Supported Ru(II) Catalysts 85 3.2.1 Structure–Activity Relationships with TpRu(L)(NCMe)Ph: Examination of Elementary Steps and Catalytic Hydrophenylation of Ethylene as a Function of Ligand L 90 3.2.2 Ethylene Hydrophenylation Catalyzed by Cationic Ru(II) Complexes Ligated by Poly(pyrazolyl)alkanes 93 3.3 Olefin Hydroarylation Catalyzed by Octahedral d6 Ir(III) Supported by the Acetylacetonate Ligand 95 3.3.1 Mechanism of Catalytic Olefin Hydrophenylation using Ir(III) Supported by the Acetylacetonate Ligand 96 3.3.2 Other d6 Ir(III) Catalysts 98 3.4 Summary: Comparison of Ru(II) and Ir(III) Catalysts for Olefin Hydroarylation 99 3.5 Future Outlook: Extension of Olefin Hydroarylation using Hydrocarbons to Earth Abundant Metals 100 References 102 4 Hydroarylation of Olefins with Complexes Bearing d8 Metal Centers 107; Benjamin A. Suslick and T. Don Tilley 4.1 Introduction 107 4.2 PtII Catalyzed Hydroarylation 109 4.2.1 PtII Hydroarylation Catalysts Bearing Anionic Bidentate (NN) Ligands 109 4.2.2 PtII Hydroarylation Catalysts Bearing Neutral Bidentate (NN) Ligands 114 4.2.3 PtII Hydroarylation Catalysts Supported by Nonnitrogen-based Ligands 119 4.2.4 Summary of PtII Catalyzed Hydroarylations 123 4.3 RhI-Catalyzed Hydroarylation 124 4.3.1 Reactions of Unfunctionalized Arenes with RhI Complexes Proceeding via Hydroarylation-LikeMechanisms 124 4.3.2 Directed ortho-Hydroarylation Catalyzed by RhI Complexes 126 4.3.3 RhI-Catalyzed Hydroarylation with Fluorinated Arenes 142 4.3.4 Summary of RhI-Catalyzed Hydroarylation 142 4.4 Directed ortho-Hydroarylation Catalyzed by IrI Complexes 144 4.5 Hydroarylation with Ni0 Complexes via NiII Intermediates 152 4.6 Formal Hydroarylation Reactions with PdII Catalysts via Heck-Like Mechanisms 155 4.6.1 Formate-Assisted PdII Catalyzed Hydroarylation 155 4.6.2 Oxidatively Coupled PdII-Catalyzed Hydroarylation with Aryltin and Arylboronic Ester Substrates 160 4.6.3 Summary of PdII-Catalyzed Formal Hydroarylation Reactions 163 4.7 Conclusions 166 References 166 5 Hydroarylation of C–C Multiple Bonds Using Nickel Catalysts 175; Yoshiaki Nakao 5.1 Introduction 175 5.2 Hydroarylation of Alkynes 175 5.3 Hydroheteroarylation of Alkynes 179 5.3.1 Hydroheteroarylation of Alkynes with five-Membered Heteroarenes 179 5.3.2 Hydroheteroarylation of Alkynes with Azine-N-oxides 182 5.3.3 Hydroheteroarylation of Alkynes with Azines 182 5.4 Hydroarylation of Alkenes 184 5.5 Hydroheteroarylation of Alkenes 185 5.5.1 Hydroheteroarylation of Alkenes with five-Membered Heteroarenes 185 5.5.2 Hydroheteroarylation of Alkenes with Azines 188 5.6 Summary and Outlook 189 References 190 6 Hydroarylation of Alkynes and Alkenes using Group 7–9 First-Row Transition Metal Catalysts 193; Naohiko Yoshikai 6.1 Introduction 193 6.2 Hydroarylation of Alkynes and Alkenes using Cobalt Catalysts 194 6.2.1 Hydroarylation of Alkynes using Low-Valent Cobalt Catalysts 194 6.2.2 Hydroarylation of Alkenes using Low-Valent Cobalt Catalysts 199 6.2.3 Hydroarylation of Alkynes and Alkenes using Cp*CoIII Catalysts 206 6.3 Hydroarylation of Alkynes and Alkenes using Iron Catalysts 208 6.3.1 Hydroarylation of Alkynes and Alkenes using Low-Valent Iron Catalysts 208 6.3.2 Hydroarylation of Alkenes using Lewis Acidic Iron Catalysts 208 6.4 Hydroarylation of Alkynes using Low-Valent Manganese Catalyst 209 6.5 Conclusions 211 6.6 Abbreviations 211 References 212 7 Hydroarylation of Alkynes using Cu, Ag, and Au Catalysts 217; Mariia S. Kirillova, Fedor M.Miloserdov, and AntonioM. Echavarren 7.1 Introduction 217 7.2 Intramolecular Hydroarylation of Alkynes 218 7.2.1 Alkyne Hydroarylation with Electron-Rich Arenes 218 7.2.1.1 Alkyne Hydroarylation with Aniline Derivatives 218 7.2.1.2 Alkyne Hydroarylation with Phenols and Phenol Ether Derivatives 225 7.2.2 Alkyne Hydroarylation with Other Arenes 231 7.2.3 Alkyne Hydroarylation with Indoles 237 7.2.3.1 Alkenylation of Indoles at the 2-Position 239 7.2.3.2 Alkenylation of Indoles at the 3-position 242 7.2.3.3 Spirocyclizations 244 7.2.3.4 More Complex Transformations Featuring a Hydroarylation of Alkynes 246 7.2.4 Alkyne Hydroarylation with Pyrroles 258 7.2.5 Alkyne Hydroarylation with Furans and Benzofurans 263 7.2.5.1 Alkenylation at the 2-Position of Furan 264 7.2.5.2 Alkenylation at the 3-Position of Furan 265 7.2.5.3 More Complex Transformations Featuring Hydroarylation of Alkynes 265 7.2.5.4 The Furan–Yne Cycloisomerization to Phenols 270 7.2.6 Alkyne Hydroarylation withThiophenes and Benzothiophenes 276 7.3 Intermolecular Hydroarylation of Alkynes 277 7.3.1 Intermolecular Hydroarylation of Alkynes with Arenes 277 7.3.2 Intermolecular Hydroarylation of Alkynes with Heteroarenes 278 7.3.2.1 N-Heterocycles 279 7.3.2.2 O-Heterocycles 282 7.4 Metal-Supported Catalysts and Their Applications in Hydroarylation of Alkynes 284 7.5 Hydroarylation of Alkynes in Total Synthesis 288 References 291 8 Catalytic Alkyne Hydroarylation Using Arylboron Reagents, Aryl Halides, and Congeners 305; Yoshihiko Yamamoto 8.1 Introduction 305 8.2 Catalyzed Alkyne Hydroarylations Using Arylboron and Arylsilicon Reagents 307 8.2.1 Rhodium-Catalyzed Reactions 308 8.2.2 Palladium-Catalyzed Reactions 315 8.2.3 Reactions Catalyzed by First Row Transition Metals 321 8.3 Catalyzed Alkyne Hydroarylations Using Aryl Halides and Arenediazonium Compounds 326 8.3.1 Intermolecular Reductive Heck Reactions 327 8.3.2 Intramolecular Reductive Heck Reactions 333 8.4 Synthetic Applications of Alkyne Hyaroarylations Using Arylboron Reagents and Aryl Halides 336 8.4.1 Sequential Processes Involving Alkyne Hydroarylations Using Arylboron Reagents and Aryl Halides 336 8.4.1.1 Synthesis of Oxygen Heterocycles 336 8.4.1.2 Synthesis of Nitrogen and Phosphorous Heterocycles 341 8.4.1.3 Synthesis of Carbocycles 346 8.4.2 Synthesis of Bioactive Compounds and Natural Products via Alkyne Hydroarylations Using Arylboron Reagents and Aryl Halides 348 8.5 Summary 352 References 354 9 Transition Metal-Catalyzed Hydroarylation of Allenes 361; Ross A.Widenhoefer <
• Edition: 1st
• Publisher Details: Weinheim : Wiley-VCH
• Publication Date: 2017
• Extent: 1 online resource
• Subjects: 547.215; Catalysis; Carbon compounds; Hydrocarbons
• Languages: English
• ISBNs: 9783527697656; 9783527697663
• Related ISBNs: 9783527340132; 9783527697632
• Notes: Note: Description based on CIP data; resource not viewed.
• Access Rights: Legal Deposit; Only available on premises controlled by the deposit library and to one user at any one time; The Legal Deposit Libraries (Non-Print Works) Regulations (UK).
• Access Usage: Restricted: Printing from this resource is governed by The Legal Deposit Libraries (Non-Print Works) Regulations (UK) and UK copyright law currently in force.