Note: Cover -- Title Page -- Copyright -- Contents -- Chapter 1 Oxidative Coupling-Bonding between Two Nucleophiles -- 1.1 Introduction/General -- 1.1.1 What is Oxidative Cross-Coupling? -- 1.1.2 Why Oxidative Cross-Coupling? -- 1.1.3 How Does Oxidative Cross-Coupling Work? -- 1.1.4 Development and Outlook -- References -- Chapter 2 Organometals as Nucleophiles -- 2.1 Classification and Applications of Organometallic Reagents -- 2.2 Csp-M and Csp-M as Nucleophiles -- 2.2.1 Alkyne-Alkyne Oxidative Coupling -- 2.2.1.1 Alkynyl-Si -- 2.2.1.2 Alkynyl-Sn -- 2.2.1.3 Alkynyl-B -- 2.2.1.4 Alkynyl-Mg -- 2.2.1.5 Alkynyl-Te -- 2.2.2 Alkyne-Cyano Oxidative Coupling -- 2.3 Csp-M and Csp2-M as Nucleophiles -- 2.4 Csp-M and Csp3-M as Nucleophiles -- 2.5 Csp2-M and Csp2-M as Nucleophiles -- 2.5.1 Homocoupling of Csp2-M -- 2.5.2 Cross-Coupling between Different Species of Csp2-M -- 2.6 Csp2-M and Csp3-M as Nucleophiles -- 2.7 Csp3-M and Csp3-M as Nucleophiles -- 2.8 Conclusions -- References -- Chapter 3 Oxidative Couplings Involving the Cleavage of C-H Bonds -- 3.1 Theoretical Understandings and Methods in C-H Bond Functionalization -- 3.1.1 Introduction -- 3.1.2 Mechanisms of C-H Cleavage by Transition Metals -- 3.1.2.1 Oxidative Addition -- 3.1.2.2 Electrophilic Substitution -- 3.1.2.3 -Bond Metathesis -- 3.1.2.4 Concerted Metalation Deprotonation (CMD) -- 3.1.2.5 1,2-Addition -- 3.1.2.6 Biomimetic C-H Oxidation -- 3.1.2.7 Carbenoid/Nitrenoid C-H Insertion -- 3.1.3 Methods for Selective C-H Bond Functionalization -- 3.1.3.1 Directed C-H Functionalization -- 3.1.3.2 Sterically Controlled C-H Functionalization -- 3.1.3.3 C-H Functionalization via Ionic Intermediates -- 3.1.3.4 C-H Functionalization via Radical Intermediates -- 3.2 Oxidative Couplings between Organometals and Hydrocarbons -- 3.2.1 C(sp)-H and Organometals as Nucleophiles. , 3.2.2 Csp2-H and Organometals as Nucleophiles -- 3.2.3 Csp3-H and Organometals as Nucleophiles -- 3.3 Oxidative Couplings between Two Hydrocarbons -- 3.3.1 C(sp)-H and C(sp)-H as Nucleophiles -- 3.3.2 C(sp)-H and C(sp2)-H as Nucleophiles -- 3.3.3 C(sp)-H and C(sp3)-H as Nucleophiles -- 3.3.4 Csp2-H and Csp2-H as Nucleophiles -- 3.3.4.1 Oxidative Coupling between Directing-Group-Containing Arenes and Unactivated Arenes -- 3.3.4.2 Oxidative Coupling of Arenes without Directing Groups -- 3.3.4.3 Intramolecular Oxidative Coupling of Unactivated Arenes -- 3.3.4.4 Oxidative Heck-Type Cross-Coupling -- 3.3.5 Csp2-H and Csp3-H as Nucleophiles -- 3.3.5.1 Intramolecular Oxidative Coupling between Aromatic Csp2-H and Csp3-H -- 3.3.5.2 Intramolecular Oxidative Coupling between Alkene Csp2-H and Csp3-H -- 3.3.5.3 Intermolecular Oxidative Coupling between Csp2-H and Csp3-H -- 3.3.6 C(sp3)-H and C(sp3)-H as Nucleophiles -- 3.4 Conclusions -- References -- Chapter 4 Bonding Including Heteroatoms via Oxidative Coupling -- 4.1 Introduction -- 4.2 Oxidative C-O Bond Formation -- 4.2.1 C-H and O-M as Nucleophiles -- 4.2.2 C-H and O-H as Nucleophiles -- 4.2.2.1 C(sp2, Aryl)-O Bond Formation -- 4.2.2.2 C(sp2, Heteroaryl, Alkenyl)-O Bond Formation -- 4.2.2.3 C(sp3, Benzyl)-O Bond Formation -- 4.2.2.4 C(sp3, Alkanes with Directing Group)-O Bond Formation -- 4.2.2.5 C(sp3, Ethers, Amines, Amides, Alkanes)-O Bond Formation -- 4.2.2.6 C(sp3, allyl)-O Bond Formation -- 4.3 Oxidative C-N Bond Formation -- 4.3.1 C(sp)-N Bond Formation -- 4.3.2 C(sp2, Arenes with Directing Group)-N Bond Formation -- 4.3.3 C(sp2, Simple Arenes)-N Bond Formation -- 4.3.4 C(sp2, Heteroaryl)-N Bond Formation -- 4.3.5 C(sp2, Alkenyl)-N Bond Formation -- 4.3.6 C(sp3, Alkyl)-N Bond Formation -- 4.3.7 C(sp3, Allyl)-N Bond Formation -- 4.4 Oxidative C-Halo Bond Formation. , 4.4.1 C-H and Halo-H as Nucleophiles -- 4.4.2 C-H and Halo-M as Nucleophiles -- 4.5 Oxidative C-S Bond Formation -- 4.5.1 C(sp2)-S Bond Formation -- 4.5.2 C(sp)-S Bond Formation -- 4.6 Oxidative C-P Bond Formation -- 4.6.1 C(sp2, Aryl)-P Bond Formation -- 4.6.2 C(sp2, Heteroaryl)-P Bond Formation -- 4.6.3 C(sp2, Alkenyl)-P Bond Formation -- 4.6.4 C(sp)-P Bond Formation -- 4.6.5 C(sp3)-P Bond Formation -- 4.7 Oxidative C-B Bond Formation -- References -- Chapter 5 Oxidative Radical Couplings -- 5.1 Introduction -- 5.2 Oxidative Radical C-C Couplings -- 5.2.1 Coupling of Csp3-H with Csp-H Bonds -- 5.2.2 Coupling of Csp3-H with Csp2-H Bonds -- 5.2.3 Coupling of Csp3-H with Csp3-H Bonds -- 5.2.4 Coupling of Csp2-H with Csp2-H Bonds -- 5.3 Oxidative Radical C-C Couplings through Cascade Process -- 5.4 Oxidative Radical C-C Couplings via C-C(N) Bond Cleavage -- References -- Index -- EULA.