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Supramolecular Catalysis

New Directions and Developments
1. Aufl.

von: Piet W.N.M. van Leeuwen, Matthieu Raynal
192,99 €
Verlag:	Wiley-VCH
Format:	PDF
Veröffentl.:	22.12.2021
ISBN/EAN:	9783527832026
Sprache:	englisch
Anzahl Seiten:	704

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Supramolecular Catalysis Provides a timely and detailed overview of the expanding field of supramolecular catalysis The subdiscpline of supramolecular catalysis has expanded in recent years, benefiting from the development of homogeneous catalysis and supramolecular chemistry. Supramolecular catalysis allows chemists to design custom-tailored metal and organic catalysts by devising non-covalent interactions between the various components of the reaction. Edited by two world-renowned researchers, Supramolecular Catalysis: New Directions and Developments summarizes the most significant developments in the dynamic, interdisciplinary field. Contributions from an international panel of more than forty experts address a broad range of topics covering both organic and metal catalysts, including emergent catalysis by self-replicating molecules, switchable catalysis using allosteric effects, supramolecular helical catalysts, and transition metal catalysis in confined spaces. This authoritative and up-to-date volume: <ul><li>Covers ligand-ligand interactions, assembled multi-component catalysts, ligand-substrate interactions, and supramolecular organocatalysis and non-classical interactions</li> <li>Presents recent work on supramolecular catalysis in water, supramolecular allosteric catalysis, and catalysis promoted by discrete cages, capsules, and other confined environments</li> <li>Highlights current research trends and discusses the future of supramolecular catalysis</li> <li>Includes full references and numerous figures, tables, and color illustrations</li></ul> Supramolecular Catalysis: New Directions and Developments is essential reading for catalytic chemists, complex chemists, biochemists, polymer chemists, spectroscopists, and chemists working with organometallics.

Inhaltsverzeichnis

Preface xix Supramolecular Catalysis: An Introduction xxi Part I Ligand–Ligand Interactions 1 1 Supramolecular Construction of Bidentate Ligands Through Self-assembly by Hydrogen Bonding 3 Felix Bauer and Bernhard Breit 1.1 Introduction 3 1.2 Formation of Bidentate Ligands Through Self-assembly via Hydrogen Bonding and Application in Hydroformylation 5 1.3 Asymmetric Hydrogenation 13 1.4 Other Catalytic Applications 17 1.5 Concluding Remarks 21 References 22 2 Self-Assembled Bidentate Ligands in Transition Metal Catalysis; From Fundamental Invention to Commercial Application 27 Alexander M. Kluwer, Xavier Caumes, and Joost N. H. Reek 2.1 Introduction 27 2.2 Metal–Ligand Interactions, the SUPRAphos Library 28 2.3 Supramolecular Bidentate Ligands Based on Hydrogen Bonds, a Toolbox for Evolutionary Catalyst Design 30 2.4 Formation of Supramolecular Pincer-Type Complexes 34 2.5 From a Supramolecular Bidentate Ligand to a Catalyst with Substrate Pre-organization 36 2.6 Outlook 37 References 38 Part II Self-assembled Nanostructures and Multi-component Assemblies 41 3 Assembled Ionic Molecular Catalysts and Ligands 43 Kohsuke Ohmatsu, Daisuke Uraguchi, and Takashi Ooi 3.1 Introduction 43 3.2 Concept of Ion-Paired Chiral Ligand 44 3.4 Conclusion 51 References 51 4 Self-amplification of Enantioselectivity in Asymmetric Catalysis by Supramolecular Recognition and Stereodynamics 55 Oliver Trapp 4.1 Introduction 55 4.2 Design of an Enantioselective Self-amplifying Catalyst Based on Noncovalent Product–Catalyst Interactions 57 4.3 The Stereodynamics of the Ligand Core 57 4.4 Design of Product–Catalyst Adducts and Catalyst Synthesis 59 4.5 Noncovalent Interaction Studies via NMR Spectroscopy 61 4.6 Self-amplifying Hydrogenation of 3,5-DNB-ΔAla-OEt 63 4.7 Concluding Remarks 64 Acknowledgments 64 References 64 5 Interlocked Molecules in Enantioselective Catalysis 69 Carel Kwamen and Jochen Niemeyer 5.1 Introduction 69 5.2 Rotaxanes in Enantioselective Catalysis 70 5.3 Catenanes in Enantioselective Catalysis 75 5.4 Molecular Knots in Enantioselective Catalysis 77 5.5 Conclusion 78 References 78 6 Catalytic Supramolecular Gels 81 Beatriu Escuder 6.1 Introduction 81 6.2 Catalytic LMWGs 82 6.3 LMWGs in Organocatalysis 82 6.4 LMWGs in Metallocatalysis 86 6.5 Multicomponent Supramolecular Materials Involving Catalytic LMWGs 87 6.6 Concluding Remarks 89 Acknowledgments 90 References 90 7 Supramolecular Helical Catalysts 93 Laurent Bouteiller and Matthieu Raynal 7.1 Introduction 93 7.2 Concept: Induction of Chirality to Metal Centers Connected to Supramolecular Helices 94 7.3 Amplification of Chirality in Two-Component Supramolecular Helical Catalysts 97 7.4 Amplification of Chirality in Three-Component Helical Catalysts 98 7.5 Switchable Asymmetric Catalysis by Reversible Assembly of Helical Catalysts 100 7.6 Dual Stereocontrol of an Asymmetric Reaction by Switchable Helical Catalysts 101 7.7 Concluding Remarks 103 Acknowledgments 104 References 104 8 Self-Assembled Multi-Component Supramolecular Catalysts for Asymmetric Reactions 107 Guanghui Ouyang, Jian Jiang, and Minghua Liu References 114 Part III Ligand–Substrate Interactions 117 9 Harnessing Ligand–Substrate Non-covalent Interactions for Control of Site-Selectivity in Transition Metal-Catalyzed C–H Activation and Cross-Coupling 119 Robert J. Phipps 9.1 Introduction 119 9.2 C–H Borylation 120 9.3 Cross-Coupling 126 9.4 Concluding Remarks 128 Acknowledgments 129 References 129 10 Supramolecular Interactions in Distal C–H Activation of (Hetero)arenes 133 Jyoti P. Biswas and Debabrata Maiti 10.1 Introduction 133 10.2 Distal C–H Activation of Arenes 133 10.3 Distal C–H Activation of Heterocycles 137 10.4 Conclusion 141 Acknowledgments 141 References 141 11 Transition-Metal-Catalyzed, Site- and Enantioselective Oxygen and Nitrogen Transfer Enabled by Lactam Hydrogen Bonds 145 Finn Burg and Thorsten Bach 11.1 Chiral Lactams as Hydrogen Bonding Sites for Enantioselective Catalysis 145 11.2 Enantioselective Addition to Olefins 147 11.3 Enantioselective C(sp 3)–H Functionalization 150 11.4 Enantioselective Oxidation of Sulfur Centers 156 11.5 Concluding Remarks 157 Acknowledgments 158 References 158 12 Supramolecular Substrate Orientation as Strategy to Control Selectivity in Transition Metal Catalysis 161 Joost N.H. Reek and Bas de Bruin 12.1 Introduction 161 12.2 Asymmetric Hydrogenation 161 12.3 Substrate Orientation in Hydroformylation Catalysis 164 12.4 Substrate Orientation in C—H Borylation 168 12.5 Second Coordination Sphere Control in Enantioselective Cobalt-catalyzed Carbene and Nitrene Transfer Reactions 170 References 174 13 Phosphine Ligands with Acylguanidinium Groups as Substrate-directing Unit 179 Felix Bauer and Bernhard Breit 13.1 Introduction 179 13.2 Hydroformylation of Alkenoic and Alkynoic Acids 179 13.3 Aldehyde Reduction and Tandem Hydroformylation–Hydrogenation 188 13.4 Concluding Remarks 197 References 198 14 Chemical Reactions Controlled By Remote Zn···N Interactions Between Substrates and Catalysts 201 Jonathan Trouvé and Rafael Gramage-Doria 14.1 Introduction 201 14.2 Organic Reactions 202 14.3 Transition Metal Catalysis 204 14.4 Conclusion 207 Acknowledgments 207 References 207 Part IV Catalysis Promoted by Discrete Cages, Capsules, and other Confined Environments 211 15 Artificial Enzymes Created Through Molecular Imprinting of Cross-Linked Micelles 213 Yan Zhao 15.1 Introduction 213 15.2 Surface-Cross-Linked Micelles (SCMs) 213 15.3 Molecularly Imprinted Nanoparticles (MINPs) via Double Cross-Linking of Micelles 215 15.4 MINP-Based Artificial Esterase 217 15.5 MINP-Based Artificial Glycosidase 219 15.6 MINP-Based Artificial Enzymes for Asymmetric Catalysis and Tandem Catalysis 223 15.7 Concluding Remarks 225 Acknowledgments 226 References 226 16 Bioinspired Catalysis Using Innately Polarized Pd 2 L 4 Coordination Cages 229 Paul J. Lusby 16.1 Introduction 229 16.2 A Coordination-Cage Host–Guest Method Based on Polar Interactions 229 16.3 From Guest Binding to Catalysis; an Artificial “Diels–Alderase” 231 16.4 Base-Free Michael Addition Catalysis 235 16.5 Turning Cage-Catalysis Inside Out 238 16.6 Concluding Remarks 239 Acknowledgments 239 References 239 17 Supramolecular Catalysis with a Cubic Coordination Cage: Contributions from Cavity and External-Surface Binding 241 ChristopherG.P.TaylorandMichaelD.Ward 17.1 Introduction: The Host Cage and Its Structure 241 17.2 Binding of Organic Guests in the Central Cavity in Water 242 17.3 Surface Binding of Anions 244 17.4 The Paradigm: Catalysis of the Kemp Elimination 245 17.5 Effects of Anion Accumulation Around the Surface: Autocatalysis 247 17.6 Catalysis with Noncavity-Bound Guests: Phosphate Ester Hydrolysis and an Aldol Condensation 249 17.7 Conclusion 251 Acknowledgments 252 References 252 18 Transition Metal Catalysis in Confined Spaces 255 Joost N.H. Reek and Sonja Pullen 18.1 Introduction 255 18.2 Template Ligand Strategies for Encapsulation of Transition Metal Catalysts 255 18.3 Catalyst Encapsulation Strategies for Solar Fuel-Related Reactions 258 18.4 Concluding Remarks and Outlook 268 References 268 19 Catalysis by Metal–Organic Cages: A Computational Perspective 271 Giuseppe Sciortino, Gantulga Norjmaa, Jean Didier Maréchal, and Gregori Ujaque 19.1 Introduction 271 19.2 Looking for a Robust Computational Framework to Study MOCs 272 19.3 Applications of Modeling to Confined Catalysis 274 19.4 Future Directions 281 References 281 20 N-heterocyclic Carbene (NHC)-Capped Cyclodextrins for Cavity-Controlled Catalysis 287 Sylvain Roland and Matthieu Sollogoub 20.1 Introduction: NHC-Capped Cyclodextrin Metal Complexes 287 20.2 Orientation of Cyclization Reactions – Five vs. Six-Membered Cycle 289 20.3 Control of Regioselectivity 291 20.4 Control of Enantioselectivity by the CD Chiral Cavity 293 20.5 Substrate Selectivity 296 20.6 Protection of Metal Centers and Promotion of Reactive Species 297 20.7 Concluding Remarks 299 Acknowledgments 299 References 299 21 Supramolecular Catalysis by Metallohosts Based on Glycoluril 303 Jeroen P.J. Bruekers, Johannes A.A.W. Elemans, and Roeland J.M. Nolte 21.1 Introduction 303 21.2 Rhodium-Based Catalytic Baskets 304 21.3 Copper-Based Catalytic Baskets 306 21.4 Porphyrin Cage Catalysts 307 21.4.1 Epoxidation of Low-Molecular-Weight Alkenes 307 21.4.2 Epoxidation of Polymeric Alkenes 311 21.4.3 Carbenoid Transfer Reactions with α-Diazoesters 315 21.5 Outlook 316 Acknowledgments 317 References 317 22 Catalysis Inside the Hexameric Resorcinarene Capsule: Toward Addressing Current Challenges in Synthetic Organic Chemistry 321 Leonidas-Dimitrios Syntrivanis and Konrad Tiefenbacher 22.1 Introduction 321 22.2 Background 321 22.3 Application to Terpene Cyclization 323 22.4 Elucidating the Prerequisites for Catalytic Activity Inside the Resorcinarene Capsule 328 22.5 Further Applications of Capsule I as Catalyst 329 22.6 Concluding Remarks 330 Acknowledgments 331 References 331 23 Supramolecular Organocatalysis Within the Nanospace of Resorcinarene Capsule 335 Carmine Gaeta, Carmen Talotta, Margherita De Rosa, Annunziata Soriente, Antonio Rescifina, and Placido Neri 23.1 Introduction 335 23.2 The Hexameric Resorcinarene Capsule 337 23.3 The Hexameric Capsule as H-bonding Organocatalyst 338 23.4 The Hexameric Capsule as Brønsted Acid Organocatalyst 339 23.5 Iminium Catalysis with a Coencapsulated Cocatalyst 341 23.6 Halogen-bond (XB) Catalysis with a Coencapsulated Cocatalyst 343 23.7 Concluding Remarks 343 Acknowledgment 344 References 344 24 Resorcin[4]arene Hexamer: From Nanocontainer to Nanocatalyst 347 Giorgio Strukul, Fabrizio Fabris, and Alessandro Scarso 24.1 Introduction 347 24.2 Resorcinarene Capsule as Nanoreactor 348 24.3 Resorcin[4]arene Capsule as Nanocatalyst 352 24.4 Concluding Remarks 357 Acknowledgments 358 References 358 Part V Supramolecular Organocatalysis and Non-classical Interactions 361 25 The Aryl-Pyrrolidine-tert-Leucine Motif as a New Privileged Chiral Scaffold: The Role of Noncovalent Stabilizing Interactions 363 Daniel A. Strassfeld and Eric N. Jacobsen 25.1 Introduction 363 25.2 Foundational Studies 364 25.3 Development of the Aryl-Pyrrolidino-tert-Leucine Catalyst Motif 366 25.4 Scope of Enantioselective Reactions and Mechanisms Promoted Effectively by Aryl-Pyrrolidine-tert-Leucine HBD Catalysts 368 25.5 Mechanisms of Enantioinduction by Aryl-Pyrrolidinetert-Leucino-H-Bond-Donor Catalysts: Case Studies 374 25.6 Concluding Remarks 380 Acknowledgments 381 References 382 26 Chiral Triazole Foldamers in Enantioselective Anion-Binding Catalysis 387 Alica C. Keuper and Olga García Mancheño 26.1 Introduction 387 26.2 Triazoles as Anion Receptors 387 26.3 Design of Foldamer Triazoles as Hydrogen Bond Donors for Anion-Binding Catalysis 388 26.4 Anion-Binding-Catalyzed Enantioselective Reissert-Type Reaction with Silylketene Acetals 389 26.5 Reaction with Different Nucleophiles 391 26.6 Nucleophilic Dearomatization of Pyrylium Derivatives 392 26.7 Folding and Cooperative Multi-Recognition Mechanism 393 26.8 Design of Catalytic Transformations Based on Anion-Template Strategies 394 26.9 Concluding Remarks 395 Acknowledgments 396 References 396 27 Supramolecular Catalysis via Organic Solids: Templates to Mechanochemistry to Cascades 401 Shweta P. Yelgaonkar and Leonard R. MacGillivray 27.1 Template Approach for [2+2] Photocycloadditions 401 27.2 State of Mechanochemistry 402 27.3 Organic Catalysis and Mechanochemistry 403 27.4 Cascade Reactions and Mechanochemistry 407 27.5 Concluding Remarks 409 Acknowledgments 409 References 409 28 Exploration of Halogen Bonding for the Catalysis of Organic Reactions 413 Revannath L. Sutar and Stefan M. Huber 28.1 Introduction 413 28.2 Halide Abstraction Reactions 415 28.3 Activation of Organic Functional Groups 418 28.4 Activation of a Metal–Halogen Bond 421 28.5 Conclusion 421 References 422 29 Chalcogen-Bonding Catalysis 427 Wei Wang and Yao Wang 29.1 Introduction 427 29.2 Challenges in Chalcogen-Bonding Catalysis 428 29.3 Discovery of Efficient Chalcogen-Bonding Catalysts 428 29.4 Chalcogen–Chalcogen Bonding Catalysis 431 29.5 Dual Chalcogen–Chalcogen Bonding Catalysis 433 29.6 Conclusion Remarks 436 Acknowledgments 437 References 437 30 Asymmetric Supramolecular Organocatalysis: The Fourth Pillar of Catalysis 441 Kengadarane Anebouselvy, Kodambahalli S. Shruthi, and Dhevalapally B. Ramachary 30.1 Introduction 441 30.2 Asymmetric Michael Additions 442 30.3 Concluding Remarks 448 Acknowledgments 448 References 448 Part VI Supramolecular Catalysis in Water 451 31 Metal Catalysis in Micellar Media 453 Giorgio Strukul, Fabrizio Fabris, and Alessandro Scarso 31.1 Introduction 453 31.2 Oxidation Reactions 454 31.3 C—C and C—X Bond Forming Reactions 457 31.4 Metal Nanoparticles in Micellar Media 461 31.5 Catalyst Surfactant Interactions 463 Acknowledgments 465 References 465 32 Surfactant Assemblies as Nanoreactors for Organic Transformations 467 Margery Cortes-Clerget, Joseph R.A. Kincaid, Nnamdi Akporji, and Bruce H. Lipshutz 32.1 Introduction 467 32.2 Micellar Catalysis: Concepts 468 32.3 Ligand Design 471 32.4 The “Nano-to-Nano” Effect 475 32.5 Reservoir Effect 476 32.6 Access to Opportunities for Telescoping Sequences 478 32.7 Industrial Applications 481 32.8 Conclusions 483 References 484 33 Compartmentalized Polymers for Catalysis in Aqueous Media 489 Fabian Eisenreich and Anja R.A. Palmans 33.1 Introduction 489 33.2 Folding a Polymer Chain in Water into a Compact Structure 491 33.3 Polymer-Supported Ru(II) Catalysis in Water 495 33.4 Polymer-Supported Cu(I) and Pd(II) Catalysis in Water 496 33.5 Polymer-Supported Organocatalysis in Water 498 33.6 Polymer-Supported Photocatalysis in Water 500 33.7 Outlook and Conclusions 501 Acknowledgments 502 References 502 34 Phosphines Modified by Cyclodextrins for Supramolecular Catalysis in Water 507 Sébastien Tilloy and Eric Monflier 34.1 Introduction 507 34.2 Synthesis and Properties of CD-Phosphine 1 (CD-P-1) 508 34.3 Synthesis and Properties of CD-Phosphine 2 (CD-P-2) 510 34.4 Synthesis and Properties of CD-Phosphine 3 (CD-P-3) 512 34.5 Synthesis and Properties of CD-Phosphine 4 (CD-P-4) 513 34.6 Concluding Remarks 514 References 515 35 Water-Soluble Yoctoliter Reaction Flasks 519 Yahya A. Ismaiel and Bruce C. Gibb 35.1 Introduction 519 35.2 Deep-Cavity Cavitands 520 35.3 The Thermodynamic and Kinetic Features of the Capsular Complexes 520 35.4 Assembly State of OA 1 and TEMOA 2 and Guest Packing Motifs Within 521 35.5 Photochemistry 523 35.6 Thermal Reactions 528 35.7 Summary and Conclusions 533 Acknowledgments 533 References 533 36 Chemical Catalyst-Promoted Regioselective Histone Acylation 537 Yuki Yamanashi and Motomu Kanai 36.1 Introduction 537 36.2 Chemical Catalyst-Mediated Synthetic Epigenetics 537 36.3 Supramolecular Catalyst Strategy for Protein Modification 538 36.4 Supramolecular Catalyst Strategy for Histone Acetylation In Vitro 538 36.5 Catalyst-Promoted Selective Acylation Targeting Proteins in Living Cells 540 36.6 Chemical Catalyst-Promoted Regioselective Histone Acylation in Living Cells 543 36.7 Concluding Remarks 544 References 544 37 Protein–Substrate Supramolecular Interactions for the Shape-Selective Hydroformylation of Long-Chain α-Olefins 547 Peter J. Deuss and Amanda G. Jarvis 37.1 Introduction 547 37.2 Design of Protein Templates for Shape-Selective ArMs 551 37.3 Introduction of a Metal–Ligand Environment into SCP-2L 552 37.4 SCP-2L as a Catalytic Scaffold 553 37.5 Phosphine Modification of Proteins 554 37.6 Application in Biphasic Hydroformylation 555 37.7 Structural Studies on the Rhodium Hydroformylases 557 37.8 Concluding Remarks 558 Acknowledgments 558 References 559 38 Supramolecular Assembly of DNA- and Protein-Based Artificial Metalloenzymes 561 Gerard Roelfes 38.1 Introduction 561 38.2 DNA-Based Artificial Metalloenzymes 562 38.3 Protein-Based Artificial Metalloenzymes 564 38.4 Synergistic Catalysis with Artificial Metalloenzymes 567 38.5 In Vivo Assembly and Application of LmrR-Based Artificial Metalloenzymes 568 38.6 Conclusions 569 References 569 Part VII Supramolecular Allosteric Catalysts and Replicators 573 39 Switchable Catalysis Using Allosteric Effects 575 Michael Schmittel 39.1 Introduction 575 39.2 Allosteric Regulation at Zinc Porphyrin Stations by Catalyst Release 576 39.3 Allosteric Regulation of Catalysis at Copper(I) Sites 580 39.4 Dynamic Allosteric Regulation of Catalysis 583 39.5 The Future: From Allosteric Regulation of Catalysis in a Network to Smart and Autonomous Mixtures 585 39.6 Concluding Remarks 586 Acknowledgments 586 References 587 40 Supramolecularly Regulated Enantioselective Catalysts 591 Anton Vidal-Ferran 40.1 Introduction 591 40.2 Seminal Work 592 40.3 Supramolecular Regulation of a Preformed Enantioselective Catalyst 593 40.4 Supramolecular Regulation of a Prochiral Ligand or Catalyst 597 40.5 Concluding Remarks 600 Acknowledgments 601 References 601 41 Emergent Catalysis by Self-Replicating Molecules 605 Kai Liu, Jim Ottelé, and Sijbren Otto 41.1 Introduction 605 41.2 Implementation of Organocatalysis in Self-Replicating Systems 607 41.3 The Implementation of Photocatalysis in Self-Replicating Systems 610 41.4 Conclusions and Outlook 612 References 612 Index 615

Autorenportrait

Piet W.N.M. van Leeuwen worked at the Koninklijke Shell Laboratorium Amsterdam (1968–1994) heading the homogeneous catalysis group, he is emeritus professor of homogeneous catalysis of the University of Amsterdam (1989–2007) and the Eindhoven University of Technology (2001–2006), the Netherlands, he was Group leader in ICIQ, Tarragona, Spain (2004–2015), and had an IDEX Chair at LPCNO in INSA-Toulouse, France (2015–2020). Matthieu Raynal is a researcher at Sorbonne Université, Paris, France. His current research focuses on the development of supramolecular helical catalysts, the design of functional chiral assemblies, and the structure-property relationship of supramolecular polymers.

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Provides a timely and detailed overview of the expanding field of supramolecular catalysis The subdiscpline of supramolecular catalysis has expanded in recent years, benefiting from the development of homogeneous catalysis and supramolecular chemistry. Supramolecular catalysis allows chemists to design custom-tailored metal and organic catalysts by devising non-covalent interactions between the various components of the reaction. Edited by two world-renowned researchers, Supramolecular Catalysis: New Directions and Developments summarizes the most significant developments in the dynamic, interdisciplinary field. Contributions from an international panel of more than forty experts address a broad range of topics covering both organic and metal catalysts, including emergent catalysis by self-replicating molecules, switchable catalysis using allosteric effects, supramolecular helical catalysts, and transition metal catalysis in confined spaces. This authoritative and up-to-date volume: <ul><li>Covers ligand-ligand interactions, assembled multi-component catalysts, ligand-substrate interactions, and supramolecular organocatalysis and non-classical interactions</li> <li>Presents recent work on supramolecular catalysis in water, supramolecular allosteric catalysis, and catalysis promoted by discrete cages, capsules, and other confined environments</li> <li>Highlights current research trends and discusses the future of supramolecular catalysis</li> <li>Includes full references and numerous figures, tables, and color illustrations</li></ul> Supramolecular Catalysis: New Directions and Developments is essential reading for catalytic chemists, complex chemists, biochemists, polymer chemists, spectroscopists, and chemists working with organometallics.