Palladium and Norbornene Cooperative Catalysis

Fundamentals and Applications

Inbunden, Engelska, 2025

Av Guangbin Dong, Guangbin Dong, USA) Dong, Guangbin (University of Chicago

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A comprehensive exploration of Pd/Norbornene (NBE) catalysis In Palladium and Norbornene Cooperative Catalysis: Fundamentals and Applications, renowned researcher Professor Guangbin Dong delivers a systematic and comprehensive discussion of Pd/NBE catalysis, including its mechanisms, scopes, applications, and current limitations. The book provides readers with the fundamental knowledge they will need to use this type of catalysis in their own research, as well as how to choose the best reaction conditions and catalyst combinations. Each of the eight chapters are written by leading experts in the Pd/NBE catalysis field. They cover topics ranging from the mechanistic foundation of Pd/NBE catalysis to the scope of the ipso and ortho functionalization, asymmetric development, a review of the Pd/NBE-catalyzed heteroarene functionalization, and more. Readers will also find: A thorough introduction to intramolecular and intermolecular cyclizationsComprehensive explorations of the annulation chemistryPractical discussions of Pd(II)-initiated reactionsA complete summary of a variety of applications in the synthesis of complex molecules and organic materials using Pd/NBE catalysisPerfect for chemistry students with an interest in transition-metal catalysis and organic synthesis. This book will also benefit academic researchers and practicing chemists.

Produktinformation

Utgivningsdatum2025-04-02
Mått170 x 244 x 15 mm
Vikt680 g
FormatInbunden
SpråkEngelska
Antal sidor320
FörlagWiley-VCH Verlag GmbH
ISBN9783527352388

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Guangbin Dong, PhD, is Professor of Chemistry at University of Chicago, USA. His current research interests include transition-metal-catalyzed C−H and C−C bonds activation, total synthesis of bioactive natural products, boron chemistry, and development of new materials. Professor Dong has received numerous scientific awards, including Elias J. Corey Award for Outstanding Original Contribution in Organic Synthesis by a Young Investigator, Tetrahedron Young Investigator award and ACS Arthur C. Cope Scholar award.

Preface xiii1 The Palladium/Norbornene-Catalyzed Annulation Chemistry: Rapid Access to Diverse Ring Structures 1Mark Lautens and Xavier Abel-Snape1.1 Introduction 11.2 Intramolecular Cyclizations 31.2.1 Electrophile Tethered to Terminating Reagent 31.2.1.1 Ortho Alkylation 31.2.1.2 Ortho Arylation 81.2.1.3 Ortho Acylation 111.2.1.4 Ortho Amination and Ipso Heck Termination 141.2.1.5 Ortho Alkenylation and Ipso Amination via Reversal of Regioselectivity 151.2.1.6 Pd(II)-Initiated Annulations 161.2.2 Aryl Halide Tethered to Terminating Reagent 171.2.2.1 Ortho Alkylation, Ortho Arylation and Ortho Amination 171.2.3 Aryl Halide Tethered to Electrophile 171.2.3.1 Ortho Alkylation 171.2.4 Aryl Halide Tethered to Electrophile and Terminating Reagent 191.2.4.1 Ortho Alkylation 191.3 Intermolecular Cyclizations Following Intermolecular Ortho Functionalization 211.3.1 Ortho Arylation 211.3.1.1 Ipso Alkyne Insertion and Ipso Formal Benzyne Insertion 211.3.2 Ortho Amination 221.3.2.1 Ipso Alkyne Insertion 221.4 Cyclizations with Three-Membered Heterocycles as Both the Electrophile and Terminating Reagent 221.4.1 2H-Azirines 231.4.2 Aziridines 241.4.3 Epoxides 251.5 Norbornene/Norbornadiene-Integrated Cyclizations 251.5.1 Norbornene 251.5.2 Norbornadiene 271.6 One-Pot Postcatalytic Intramolecular Cyclizations 291.6.1 Postcatalytic Intramolecular Michael Additions 291.6.1.1 Ortho Alkylation 291.6.1.2 Ortho Arylation 301.6.2 Postcatalytic Intramolecular Addition to Norbornyl Moiety 311.7 Summary 32References 332 Diverse Ipso Arene Functionalization by the Palladium/Norbornene Cooperative Catalysis 45Bo-Sheng Zhang and Yong-Min Liang2.1 Introduction 452.2 Ipso Functionalization Reaction in the Pd/NBE Catalytic Cycle 462.2.1 The Role of Ipso Functionalization Reaction in the Catalytic Cycle 462.2.2 Competitive or Side Reactions of Ipso Functionalization 462.2.2.1 Competitive Pathways Between Ipso Functionalization and NBE Insertion 462.2.2.2 Compatibility Between Electrophile Reagents and Ipso Functionalization Reagents 482.2.2.3 Process of NBE Extrusion and Ipso Functionalization 492.2.2.4 Dehalogenation Reaction and Ipso Functionalization Reaction 512.3 Type of Ipso Functionalization Reactions 522.3.1 Alkenylation Reaction 522.3.1.1 Heck Coupling 522.3.1.2 Carbene Coupling 582.3.1.3 Allenylation Reaction 592.3.2 Alkynylation Reactions (Sonogashira Coupling) 612.3.3 Arylation Reactions 612.3.3.1 Suzuki Coupling 612.3.3.2 Ipso C–H Arylation 642.3.3.3 Decarboxylation Coupling Reaction 672.3.4 Alkylation Reaction 672.3.4.1 Coupling Reaction of Boron Reagents 672.3.4.2 Coupling Reaction of Germanium Reagents 672.3.4.3 Ipso Ketone α-Arylation 692.3.4.4 C–H Activation of Inert Alkyl Groups 712.3.4.5 The C—C Bond Cleavage Reaction 712.3.4.6 The 1,4-Pd Shift 722.3.5 Hydrogenation Reaction 742.3.6 Cyanation Reaction 742.3.7 Borylation Reaction 762.3.8 The Construction of C—N Bond 762.3.9 The Construction of C—O Bond 762.3.10 The Construction of C—S or C—Se Bonds 782.3.11 Ipso Iodination 792.4 Prospects and Challenges of Ipso Functionalization 80References 813 Diverse Ortho C—H Functionalization by the Palladium/Norbornene Cooperative Catalysis 89Xin Liu and Guangbin Dong3.1 Introduction 893.2 Carbon-Electrophile 913.2.1 Ortho Alkylation 913.2.1.1 Alkylation Using Alkyl Halides 913.2.1.2 Alkylation Using Methyl Sulfonates, Trimethylphosphate, and Phenyltrimethylammonium Salt 923.2.1.3 Annulation Using 2H-Azirines 963.2.1.4 Alkylation Using Epoxides 973.2.1.5 Alkylation Using Aziridines 973.2.1.6 Alkylation Using Ethers and TMSI 983.2.2 Ortho Arylation 993.2.2.1 “Ortho Effect” in the Pd/NBE Catalysis 993.2.2.2 Arylation Using Aryl Halides 1013.2.2.3 Homo Ortho Arylation 1033.2.2.4 Cross Ortho Arylation and the Chelating Effect 1033.2.2.5 Arylation Using Aryl Diazonium Salts 1053.2.3 Ortho Acylation 1073.2.3.1 Acylation Using Acid (Mixed) Anhydrides, Acid Chlorides, and Carboxylic Acids 1073.2.3.2 Carboxylation Using Thioesters and Selenides 1093.2.3.3 Alkoxycarbonylation and Aminocarbonylation 1103.3 Nitrogen-Electrophile 1123.3.1 Ortho Amination 1123.3.1.1 Amination Using N-Benzoyloxyamines 1133.3.1.2 Amination Using Dialkylamino Carbonates 1143.4 Sulfur-Electrophile 1163.4.1 Ortho Thiolation 1163.4.1.1 Thiolation Using Aryl or Alkyl Thiosulfonates 1163.4.1.2 Thiolation Using Aryl or Alkyl Sulfenamides 1163.5 Oxygen-Electrophile 1173.5.1 Ortho Alkoxylation 1173.6 Conclusion and Outlook 119References 1214 Asymmetric Palladium/Norbornene Cooperative Catalysis 129Shuming Zhan and Zhenhua Gu4.1 Introduction 1294.2 Stereochemistry Controlled by the Substrate 1314.2.1 Intramolecular Chirality Transfer 1314.2.2 Intermolecular Chirality Transfer 1324.3 Catalytic Asymmetric Transformations Controlled by Chiral Ligands 1384.3.1 Catalytic Asymmetric Transformations Controlled by Chiral Phosphine Ligands 1384.3.2 Catalytic Asymmetric Transformation Controlled by Chiral Amino Acids 1394.4 Catalytic Asymmetric Transformation Controlled by Chiral Norbornenes 1424.4.1 Desymmetrization 1424.4.2 Kinetic Resolution 1444.4.3 Enantioselective Transformations 1474.5 Summary and Outlook 152References 1545 Pd(II)-Initiated Palladium/Norbornene Cooperative Catalysis 157Hong-Gang Cheng, Kevin Wu, Qianghui Zhou, and Jin-Quan Yu5.1 Introduction 1575.2 Pd/NBE-catalyzed C–H Functionalization of NH-containing Heteroarenes 1595.2.1 C2 Alkylation of NH-Indoles and NH-Pyrroles 1595.2.1.1 C2 Alkylation of NH-Indoles 1595.2.1.2 C2 Alkylation of NH-Pyrroles and C1 Alkylation of NH-Carbazoles 1645.2.2 C2 Arylation of NH-Indoles 1665.3 Directing Group-Enabled meta-C–H Functionalization of Arenes 1675.3.1 Directing Group-Enabled meta-C–H Alkylation of Arenes 1685.3.2 Directing Group-Enabled meta-C–H Arylation of Arenes 1705.3.2.1 Amide as Directing Group 1705.3.2.2 Tertiary Amine as Directing Group 1725.3.2.3 Sulfonamide as Directing Group 1725.3.2.4 Pyridine Derivative as Directing Group 1735.3.2.5 Acetal-based Quinoline as Directing Group 1755.3.2.6 Free Carboxylic Acid as Directing Group 1755.3.3 Directing Group-Enabled meta-C–H Chlorination of Arenes 1765.3.4 Directing Group-Enabled meta-C–H Amination of Arenes 1765.3.5 Directing Group-Enabled meta-C–H Alkynylation of Arenes 1785.3.6 Directing Group-Enabled Distal C–H Functionalization of Z-Alkenes 1785.4 Directing Group-Free Mono- and Difunctionalization of (Hetero)Arenes 1795.4.1 Directing Group-Free meta-C–H Arylation of (Hetero)Arenes 1795.4.2 Directing Group-Free Difunctionalization of Heterarenes 1815.5 Template-Enabled Remote C–H Functionalization 1835.6 Enantioselective Remote C–H Functionalization 1845.7 Borono-Catellani Reactions 1885.8 Conclusion and Outlook 190References 1946 Functionalization of Heteroarenes by the Palladium/Norbornene Cooperative Catalysis 199Jung Min Joo6.1 Introduction 1996.2 Pd/NBE Reactions of Five-Membered Haloheteroarenes 2006.2.1 Reactions of Haloheteroarenes without Incorporation of NBE 2006.2.2 Reactions of Haloheteroarenes with Incorporation of NBE 2026.3 Pd/NBE Reactions of Six-Membered Haloheteroarenes 2066.3.1 Reactions of Six-Membered Haloheteroarenes without Incorporation of Nbe 2066.3.2 Reactions of Six-Membered Haloheteroarenes with Incorporation of Nbe 2116.4 Pd/NBE Reactions of Parent Heteroarenes 2146.5 Conclusion 219List of Abbreviations 219Acknowledgments 219References 2197 Addressing the Substrate Limitation in the Palladium/Norbornene Cooperative Catalysis 225Zhao Wu7.1 Introduction 2257.2 Ortho Constraint 2277.2.1 “Ortho Effect” and “Ortho Constraint” 2277.2.2 Addressing the Ortho Constraint with Bridgehead-Substituted NBEs 2307.2.3 Annulation with the C7-Modified NBE 2347.2.4 Hybrid Cycloolefin Ligand Strategy 2357.3 Meta Constraint 2377.3.1 Addressing the Meta Constraint with the C2-Amide-Substituted NBE 2417.4 Aryl Iodide Constraint 2437.4.1 Aryl Sulfonates 2447.4.2 Aryl Bromides 2467.5 Beyond Aromatic Substrates 2517.5.1 Partially Aromatic Substrates 2527.5.2 α-Alkylation and Arylation of Alkenyl Triflates and Bromides 2537.5.3 α-Amination of Alkenyl Triflates: Formal Carbonyl 1,2-Transposition 2557.5.4 α-Carbamoylation of Alkenyl Triflates 2577.5.5 Distal Alkenyl C—H Bond Functionalization 2587.6 Conclusions and Outlook 260Acknowledgments 260References 2618 Application of the Palladium/Norbornene Cooperative Catalysis to Synthesis of Natural Products and Materials 265Jianchun Wang8.1 Applications in Synthesis of Natural Products and Drugs 2658.1.1 Synthesis Using Ortho Functionalization of Aryl Halides 2658.1.1.1 Synthesis Using Ortho Alkylation Reactions 2678.1.1.2 Synthesis Using Ortho Arylation Reactions 2738.1.1.3 Synthesis Using Ortho Amination Reactions 2758.1.1.4 Synthesis Using Ortho Acylation Reactions 2778.1.2 Synthesis Using 2-Alkylation of Indoles 2798.1.3 Synthesis Using Ortho Functionalization of Vinyl Substrates 2838.2 Applications in Synthesis of Organic Aromatic Materials 2848.3 Summary 290References 291Index 295