Strategies for Palladium-Catalyzed Non-directed and Directed C bond H Bond Functionalization (Latest Trends in Palladium Chemistry)

__Strategies for Palladium-Catalyzed Non-directed and Directed C-H Bond Functionalization__ portrays the complete scope of these two aspects of C-H bond functionalization in a single volume for the first time. Featured topics include the influence of palladacyclic systems in C-H bond functionalization (need for newer catalytic systems for better efficiency), mechanistic aspect of the functionalization strategies leading to better systems, and applications of these methodologies to natural product synthesis and material synthesis. Reactions Under Phosphine-Free Conditions or Without Additional Phosphine Ligands -- 3.3 Reactions With Pseudohalides -- 3.3.1 Palladium-Catalyzed C-H/C-O Cross-Coupling Reactions With Aryl Sulfonates -- 3.3.1.1 Polyfluoroarenes -- 3.3.1.2 Heteroarenes -- 3.4 Conclusion -- References -- 4 Palladium-Catalyzed Directed Arylation of Unactivated C(sp3)-H Bonds -- 4.1 Introduction -- 4.2 Palladium-Catalyzed C(sp3)-H Arylation Directed by Monodentate DGs -- 4.3 Palladium-Catalyzed C(sp3)-H Arylation Directed by Bidentate DGs -- 4.4 Palladium-Catalyzed C(sp3)-H Arylation Using Transient DGs -- 4.5 Palladium-Catalyzed Asymmetric C(sp3)-H Arylation -- 4.5.1 Palladium-Catalyzed Enantioselective C(sp3)-H Arylation With Chiral Ligands -- 4.5.2 Palladium-Catalyzed Asymmetric C(sp3)-H Arylation With Chiral Auxiliaries -- 4.6 Conclusions and Outlook -- References -- 5 C-H Bond Functionalization at the Benzene Core of Indoles and Indolines (Excluding C-2 and C-3) -- 5.1 Palladium-Catalyzed C-H Bond Functionalization of Indole -- 5.1.1 C-H Bond Alkenylation of Indole at the C-4 Position -- 5.1.2 C-H Bond Arylation and Alkenylation of Indole at the C-7 Position -- 5.2 Palladium-Catalyzed C-H Bond Functionalization of Indolines -- 5.2.1 C-H Bond Functionalization at the C-7 Position of Indoline -- 5.2.1.1 C-H Bond Arylation of Indoline at the C-7 Position -- 5.2.1.2 C-H Bond Alkenylation of Indoline at the C-7 Position -- 5.2.1.3 C-H Bond Acylation of Indoline at the C-7 Position -- 5.2.1.4 C-H Bond Carbonylation of Indoline at the C-7 Position -- 5.2.1.5 C-H Bond Alkylation of Indoline at the C-7 Position -- 5.2.2 C-C Bond Formation at the C-6 Position of Indoline -- 5.3 Conclusions -- List of Abbreviations -- References -- 6 Palladium-Catalyzed Carbonylative and Carboxylative C-H Functionalization Reactions: Importance and Role of Regioselectivity -- 6.1 Introduction 6.1.1 Introduction to Carbonylation Chemistry -- 6.1.2 Classification of Types of Carbonylation Reactions -- 6.1.3 Difference Between Carbonylative C-H Functionalization and Its Noncarbonylative Counterpart -- 6.2 Carbonylative C-H Functionalization of Arenes in the Presence of Directing Group -- 6.2.1 Introduction to Directing Groups -- 6.2.2 Regioselective Functionalization of Arenes in the Presence of Directing Groups -- 6.2.2.1 Amidine and Oxime as Directing Groups -- 6.2.2.2 Amide and Sulfonamide as Directing Groups -- 6.2.2.3 Amine as a Directing Group -- 6.2.2.4 Carboxylic Acid as a Directing Group -- 6.2.2.5 Nitrogen Containing Heterocycle as a Directing Group -- 6.2.2.6 Hydroxyl Functionality as a Directing Group -- 6.2.2.7 Ketone as a Directing Group -- 6.3 Carbonylative C(sp2)-H Functionalization of Heteroarenes -- 6.3.1 Introduction -- 6.3.2 Carbonylative C-H Functionalization of Heteroarenes Containing a Single Heteroatom -- 6.3.3 Carbonylative C-H Functionalization of Heteroarenes Containing Multiple Heteroatoms -- 6.4 Carboxylative C-H Bond Functionalization -- 6.4.1 Introduction -- 6.4.2 Palladium-catalyzed Carboxylative C-H Functionalization -- 6.5 Conclusion and Future Outlook -- References -- 7 Flow Chemistry Perspective for C-H Bond Functionalization -- 7.1 Introduction -- 7.2 Advantages of Using Continuous-Flow Microreactor Technology for C-H Activation -- 7.3 Cross-Dehydrogenative Coupling in Continuous Flow -- 7.4 Rh-Catalyzed C-H Activation Reactions in Continuous Flow -- 7.5 Palladium-Catalyzed C(sp3)-H Activation Reactions in Continuous Flow -- 7.6 Ru-Catalyzed C-H Activation Reactions in Continuous Flow -- 7.7 Intramolecular C-H Activation Reactions in Continuous Flow -- 7.8 Ortho-Directed Hydrogen/Deuterium Isotope Exchange via Iridium-Catalyzed C-H Activation -- 7.9 Conclusion -- References 8 Directed Meta-Selective C-H Bond Functionalizations -- 8.1 Introduction -- 8.2 Directing Group Assisted Meta-C-H Functionalization -- 8.2.1 Nitrile-based Directing Group Assisted Meta-C-H Functionalization -- 8.2.1.1 Olefination -- 8.2.1.2 Arylation -- 8.2.1.3 Oxygenation -- 8.2.2 Nonnitrile-based Directing Group Assisted Meta-C-H Functionalization -- 8.3 Ortho-Directing Group-Assisted and Norbornene-Mediated Meta-C-H Functionalization -- 8.4 Formal Meta-C-H Functionalization Using a Traceless Directing Group -- 8.5 Conclusion -- Abbreviations -- References -- 9 Recent Advances in Distal Aliphatic sp3 C-H Functionalization -- 9.1 Introduction -- 9.2 Scope of Functionalization -- 9.2.1 Arylation -- 9.2.2 Alkylation -- 9.2.3 Olefination -- 9.2.4 Cyclization/amination -- 9.2.5 Borylation -- 9.2.6 Acetoxylation -- 9.2.7 Cyanomethylation -- 9.2.8 Carbonylation -- 9.4 Conclusion -- References -- 10 Palladacycles for Directed and Nondirected C-H Bond Functionalization of (Hetero)arenes -- 10.1 Introduction -- 10.2 Palladacycle PreCatalyst in C-H Functionalization -- 10.3 Palladacycle Intermediate in C-H Functionalization -- 10.3.1 Pyridinyl-Based Palladacycle -- 10.3.2 Quinolinyl-Based Palladacycle -- 10.3.3 Amine-Based Palladacycle -- 10.3.4 Azole and Oxime Ether-Based Palladacycle -- 10.3.5 Amide-Based Palladacycle -- 10.3.6 Ketone and Ester-Based Palladacycles -- 10.3.7 Anilide-Based Palladacycle -- 10.3.8 Carboxylic Acid-Based Palladacycle -- 10.3.9 Sulfur-Based Palladacycle -- 10.3.10 Bis-Chelated Palladacycle -- 10.3.11 Other Palladacycles in C-H Functionalizations -- 10.4 Conclusion -- Abbreviations -- References -- 11 Mechanistic/Organometallic Aspects of Palladium-Catalyzed C-H Bond Functionalization -- 11.1 Introduction -- 11.2 Early Findings -- 11.3 Palladium-Catalyzed C-H Activation Pathways Front Cover -- Strategies for Palladium-Catalyzed Non-Directed and Directed C-H Bond Functionalization -- Copyright Page -- Contents -- List of Contributors -- Foreword -- 1 Introduction -- 2 Directed C-H Bond Functionalization Strategies for Synthesis -- 2.1 Introduction -- 2.2 Ortho-Palladated C-H Bond Functionalization via Directing Group Effect -- 2.2.1 Effect of Coordination Capacity on Functionalization -- 2.2.1.1 Heterocycles as Directing Groups for Palladium-Catalyzed C-H Bond Functionalization -- 2.2.1.2 Anilides and Ureas as Directing Group for Palladium-Catalyzed C-H Bond Functionalization -- 2.2.1.3 Amides as a Directing Group for Palladium-Catalyzed C-H Bond Functionalization -- 2.2.1.4 Carboxylic acids as a Directing Group for Palladium-Catalyzed C-H Bond Functionalization -- 2.2.1.5 Carbonyls (Aldehydes and Ketones) as Directing Groups for Palladium-Catalyzed C-H Bond Functionalization -- 2.2.1.6 Other Directing Groups for Palladium-Catalyzed C-H Bond Functionalization -- 2.3 Conclusion -- References -- 3 Nondirected C-H Bond Functionalizations of (Hetero)arenes -- 3.1 Introduction -- 3.2 Reactions With Halides -- 3.2.1 Pd-catalyzed C-H/C-X Cross-Coupling Reactions Between an Arene and an Aryl Halide -- 3.2.1.1 Simple Arenes -- 3.2.1.2 Polyfluoroarenes -- 3.2.2 Pd-catalyzed C-H/C-X Cross-Coupling Reactions Between a Heteroarene and an Aryl Halide -- 3.2.2.1 Pyrroles and Indoles -- 3.2.2.2 Imidazoles -- 3.2.2.3 Pyrazoles and Indazoles -- 3.2.2.4 Thiophenes and Benzothiophenes -- 3.2.2.5 Furans and Benzofurans -- 3.2.2.6 Thiazoles and Benzothiazoles -- 3.2.2.7 Oxazoles and Benzoxazoles -- 3.2.2.8 Fused Heteroarenes -- 3.2.2.9 N-Oxides -- 3.2.2.10 Azoles and Other Heteroarenes -- Reactions Using Palladium Complexes -- Reactions Involving Addition of Phosphine Ligands Content: Front-matter,Copyright,List of Contributors,ForewordEntitled to full textChapter 1 - Introduction, Pages 1-8, Aniruddha Dey, Anant R. Kapdi, Debabrata Maiti Chapter 2 - Directed CH Bond Functionalization Strategies for Synthesis, Pages 9-48, Ian J.S. Fairlamb, Anant R. Kapdi Chapter 3 - Nondirected CH Bond Functionalizations of (Hetero)arenes, Pages 49-166, Shun-Man Wong, Fuk-Yee Kwong Chapter 4 - Palladium-Catalyzed Directed Arylation of Unactivated C(sp3)H Bonds, Pages 167-203, Bin Liu, Ye-Qiang Han, Fang Hu, Bing-Feng Shi Chapter 5 - CH Bond Functionalization at the Benzene Core of Indoles and Indolines (Excluding C-2 and C-3), Pages 205-232, Lin-Yu Jiao, Martin Oestreich Chapter 6 - Palladium-Catalyzed Carbonylative and Carboxylative CH Functionalization Reactions: Importance and Role of Regioselectivity, Pages 233-274, Prashant Gautam, Bhalchandra M. Bhanage Chapter 7 - Flow Chemistry Perspective for CH Bond Functionalization, Pages 275-288, Gabriele Laudadio, Timothy Noël Chapter 8 - Directed Meta-Selective CH Bond Functionalizations, Pages 289-325, Gang Li Chapter 9 - Recent Advances in Distal Aliphatic sp3 CH Functionalization, Pages 327-355, Aniruddha Dey, Uttam Dhawa, Debabrata Maiti Chapter 10 - Palladacycles for Directed and Nondirected CH Bond Functionalization of (Hetero)arenes, Pages 357-415, Vineeta Soni, Benudhar Punji Chapter 11 - Mechanistic/Organometallic Aspects of Palladium-Catalyzed CH Bond Functionalization, Pages 417-452, Vijay Gayakhe, Aniket Gholap, Anant R. Kapdi Chapter 12 - Recent Developments in Palladium-Catalyzed Natural Product Synthesis via CH Activation, Pages 453-470, Neetipalli Thrimurtulu, Aniruddha Dey, Debabrata Maiti, Chandra M.R. Volla Index, Pages 471-486

Strategies for Palladium-Catalyzed Non-directed and Directed C-H Bond Functionalization portrays the complete scope of these two aspects of C-H bond functionalization in a single volume for the first time. Featured topics include the influence of palladacyclic systems in C-H bond functionalization (need for newer catalytic systems for better efficiency), mechanistic aspect of the functionalization strategies leading to better systems, and applications of these methodologies to natural product synthesis and material synthesis.

• Addresses the involvement of catalytic systems (palladacycles) for better functionalization of (hetero)arenes to emphasize the need for developing better, more selective systems
• Covers the use of powerful mechanistic tools for understanding and assisting the development of better functionalization strategies
• Discusses the finer aspects of C-H bond functionalization, such as control of regioselectivity with or without directing groups
• Includes a chapter detailing the synthesis of naturally occurring molecules or functional molecules via both pathways for assessing the applicability of the functionalization strategies

11.3.1 Electrophilic Aromatic Substitution (SEAr Mechanism) -- 11.3.2 Oxidative Addition Mechanism -- 11.3.3 Concerted Metalation Deprotonation Mechanism -- 11.3.4 Heck-Type Carbometalation Mechanism -- 11.4 Conclusion -- Acknowledgments -- List of Abbreviations -- References -- 12 Recent Developments in Palladium-Catalyzed Natural Product Synthesis via C-H Activation -- 12.1 Introduction -- 12.2 Total Synthesis of Aspidospermidine -- 12.2.1 Total Synthesis of Goniomitine -- 12.3 Total Synthesis of (+) -Lithospermic Acid -- 12.4 Total Synthesis of Pipercyclobutanamide A -- 12.5 Total Synthesis of Piperarborenine B and D -- 12.6 Total Synthesis of Podophyllatoxin -- 12.7 Total Synthesis of Clavicipitic Acid -- 12.8 Total Synthesis of Hibispeptin A -- 12.9 Divergent Synthesis of Aeruginosins (sp3 C-H Alkenylation and Arylation) -- 12.10 Total Synthesis of (+) Linoxepin -- 12.11 Rapid Total Synthesis of Rhazinal -- 12.12 Total Synthesis of Gamendazole -- 12.13 Total Synthesis of (+/- ) Rhazinilam -- 12.14 Conclusion -- References -- Index -- Back Cover