Tharmalingam Punniyamurthy, PhD is Professor of Chemistry and Dean of Faculty Affairs at the Indian Institute of Technology Guwahati, India. Anil Kumar, PhD is Professor in the Department of Chemistry at the Birla Institute of Technology and Science, Pilani, India.

• ContentsList of Contributors xiii8 Functionalization of Pyridines, Quinolines, and Isoquinolines 357Jun Zhou and Bing-Feng Shi8.1 Introduction 3578.2 C2-Selective Functionalization 3588.3 C3-Selective Functionalization 3708.4 C4-Selective Functionalization 3788.5 C8-Selective Functionalization 3828.6 Summary and Conclusions 3879 Transition Metal-Catalyzed C-H Bond Functionalization of Diazines and Their Benzo Derivatives 393Christian Bruneau and Rafael Gramage-Doria9.1 Introduction 3939.2 Carbon-carbon Bond Formation 3949.3 Carbon-nitrogen Bond Formation 4209.4 Carbon-oxygen Bond Formation 4249.5 Carbon-sulfur Bond Formation 4249.6 Carbon-boron Bond Formation 4259.7 Carbon-silicon Bond Formation 4259.8 Carbon-halogen Bond Formation 4279.9 Conclusions 428Acknowledgments 42910 Functionalization of Chromenes and Their Derivatives 435Laura Cunningham, Sundaravel Vivek Kumar, and Patrick J. Guiry10.1 Introduction 43510.2 2 H-Chromenes 43510.3 2 H-Chromene-ones (Coumarins) 43710.4 4 H-Chromene 45910.5 4 H-Chromenones (Chromones) 46211 Transition Metal-Catalyzed C–H Functionalization of Imidazo-fused Heterocycles 485Rajeev Sakhuja and Anil Kumar11.1 Introduction 48511.2 C–C Bond Formation 48611.3 C–S/Se Bond Formation 52511.4 C–N Bond Formation 53211.5 C–P Bond Formation 53311.6 C–Si Bond Formation 53511.7 Conclusions 535Acknowledgments 53612 Dehydrogenative Annulation of Heterocycles: Synthesis of Fused Heterocycles 543Neha Jha and Manmohan Kapur12.1 Dehydrogenative Coupling: An Overview 54312.2 Importance of Heterocycles and Their Fused Congeners 54512.3 Metal-Catalyzed Dehydrogenative-coupling Reactions: Formation of C–Z Bonds 54612.4 Conclusions 56213 C–H Functionalization of Saturated Heterocycles Beyond the C2 Position 567Amalia-Sofia Piticari, Natalia Larionova, and James A. Bull13.1 Introduction 56713.2 Heterocycle Functionalization with a C2 Directing Group 56713.3 Heterocycle Functionalization with C3 Directing Groups 58613.4 Heterocycle Functionalization with a C4 Directing Group 59413.5 Transannular Heterocycle Functionalization with N-linked Directing Groups 59813.6 Conclusions 60314 Asymmetric Functionalization of C–H Bonds in Heterocycles 609Olena Kuleshova and Laurean Ilies14.1 Introduction 60914.2 Enantioselective C–H Activation 60914.3 C–H Activation Followed by Enantioselective Functionalization 61514.4 Conclusions and Perspectives 62715 Transition Metal-Catalyzed C–H Functionalization of Nucleoside Bases 631Yong Liang and Stanislaw F. Wnuk15.1 Introduction 63115.2 Direct Functionalization of the C5-H Bond in Uracil Nucleosides 63215.3 Direct Functionalization of C6-H Bond in Uracil 63715.4 Inverted C–H Functionalization of Uracil Nucleosides 64015.5 Direct C2-H Functionalization of Adenosine 64115.6 Direct C6-H Functionalization of Purine Nucleoside 64215.7 Direct Activation of C8-H Bond in Purine and Purine Nucleosides 64515.8 Conclusions 65016 C–H Activation for the Synthesis of C1-(hetero)aryl Glycosides 657Morgane de Robichon, Juba Ghouilem, Angélique Ferry, and Samir Messaoudi16.1 General Introduction 65716.2 Classical Methods to Prepare C-aryl Glycosides 65716.3 Directed C-H Activation Approach 65816.3.a Directed Csp2-Csp2 Bond Formation 65916.3.a.1 Directing Group Attached to the Aryl Partner 65916.3.a.2 Directing Group Attached to the Sugar Nucleus 66116.3.b Directed Csp2-Csp3 Bond Formation 66216.3.b.1 The Directing Group (DG) Attached to the Coupling Partner 66216.3.b.2 The Directing Group Attached to the Sugar Nucleus 67516.4 Conclusions and Perspectives 67917 Late-stage C–H Functionalization: Synthesis of Natural Products and Pharmaceuticals 683Harshita Shet and Anant R. Kapdi17.1 Introduction 68317.2 Synthesis of (±)-Ibogamine 68417.3 Synthesis of YD-3 and YC-1 (C–H Arylation of Indazoles) 68517.4 Synthesis of Complanadine A 68517.5 Synthesis of Diptoindonesin G (C–H Arylation of Benzofuran) 68617.6 Synthesis of Dragmacidin D (C–H Arylation of Indoles at the C3 Position) 68717.7 Synthesis of Celecoxib (C–H Arylation of Pyrazoles) 68817.8 Synthesis of Aspidospermidine 68917.9 Synthesis of Pipercyclobutanamide A 69017.10 Synthesis of Nigellidine Hydrobromide 69117.11 Synthesis of (+)-Linoxepin 69117.12 Synthesis of (±)-Rhazinal 69217.13 Synthesis of Podophyllotoxin (C–H Arylation) 69317.14 Synthesis of (±)-Rhazinilam 69417.15 Synthesis of Aeruginosins (sp3 C–H Alkenylation and Arylation) 69417.16 Synthesis of Gamendazole 69617.17 Synthesis of Beclabuvir (BMS-791325) 69717.18 Conclusions 69818 Late-stage Functionalization of Pharmaceuticals, Agrochemicals, and Natural Products 703François Richard, Elias Selmi-Higashi, and Stellios Arseniyadis18.1 C–H Methylation and Alkylation 70418.2 C–H Arylation and Olefination 70518.3 Formation of Other C−C Bonds 71118.4 C–H Hydroxylation 71418.5 C–H Amination 71518.6 C–H Trifluoromethylation 71618.7 C–H Difluoromethylation 71618.8 C–H Fluorination 71818.9 C–H Silylation 71818.10 C–H Phosphorylation 71918.11 C–H Deuteration and Tritiation 72018.12 Conclusions 723Index 727Brief ContentsVolume 1:List of Contributors xiiiPreface xvii1 Historical Perspective and Mechanistic Aspects of C–H Bond Functionalization 1Tariq M. Bhatti, Eileen Yasmin, Akshai Kumar, and Alan S. Goldman2 Recent Advances in C–H Functionalization of Five–Membered Heterocycles with Single Heteroatoms 61B. Prabagar and Zhuangzhi Shi3 Functionalization of Five-membered Heterocycles with Two Heteroatoms 109Jung Min Joo4 Transition Metal-Catalyzed C–H Functionalization of Indole Benzenoid Ring 155Vikash Kumar, Rajaram Maayuri, Lusina Mantry, and Parthasarathy Gandeepan5 Transition Metal-Catalyzed C2 and C3 Functionalization of Indoles 193Pinki Sihag, Meledath Sudhakaran Keerthana, and Masilamani Jeganmohan6 C(sp2)–H Functionalization of Indolines at the C7-Position 251Neeraj Kumar Mishra and In Su Kim7 Transition Metal-Catalyzed C–H Functionalization of Benzofused Azoles with Two or More Heteroatoms 319Tanumay Sarkar, Subhradeep Kar, Prabhat Kumar Maharana, Tariq. A. Shah, and Tharmalingam PunniyamurthyVolume 2:List of Contributors xiii8 Functionalization of Pyridines, Quinolines, and Isoquinolines 357Jun Zhou and Bing-Feng Shi9 Transition Metal-Catalyzed C-H Bond Functionalization of Diazines and Their Benzo Derivatives 393Christian Bruneau and Rafael Gramage-Doria10 Functionalization of Chromenes and Their Derivatives 435Laura Cunningham, Sundaravel Vivek Kumar, and Patrick J. Guiry11 Transition Metal-Catalyzed C–H Functionalization of Imidazo-fused Heterocycles 485Rajeev Sakhuja and Anil Kumar12 Dehydrogenative Annulation of Heterocycles: Synthesis of Fused Heterocycles 543Neha Jha and Manmohan Kapur13 C–H Functionalization of Saturated Heterocycles Beyond the C2 Position 567Amalia-Sofia Piticari, Natalia Larionova, and James A. Bull14 Asymmetric Functionalization of C–H Bonds in Heterocycles 609Olena Kuleshova and Laurean Ilies15 Transition Metal-Catalyzed C–H Functionalization of Nucleoside Bases 631Yong Liang and Stanislaw F. Wnuk16 C–H Activation for the Synthesis of C1-(hetero)aryl Glycosides 657Morgane de Robichon, Juba Ghouilem, Angélique Ferry, and Samir Messaoudi17 Late-stage C–H Functionalization: Synthesis of Natural Products and Pharmaceuticals 683Harshita Shet and Anant R. Kapdi18 Late-stage Functionalization of Pharmaceuticals, Agrochemicals, and Natural Products 703François Richard, Elias Selmi-Higashi, and Stellios ArseniyadisIndex 727