Iron-Catalyzed C-H/C-H Coupling for Synthesis of Functional Small Molecules and Polymers [electronic resource] / Takahiro Doba.

Intro
Supervisor's Foreword
Abstract
Acknowledgements
List of Publications
Contents
1 General Introduction
1.1 Transition-Metal-Catalyzed C-H/C-H Coupling
1.2 Requirement of Strong Oxidant in Transition-Metal-Catalyzed C-H/C-H Coupling
1.3 Iron-Catalyzed Directed C-H Activation
1.4 Iron-Catalyzed Regioselective Thienyl C-H Activation
1.5 Objective and Outline of This Thesis
References
2 Iron-Catalyzed Regioselective Thienyl C-H/C-H Homocoupling
2.1 Introduction
2.2 Initial Discovery
2.3 Catalyst Poisoning by Alkene

2.4 Diketone as a Mild Oxidant
2.5 Effect of Reaction Parameters
2.6 Substrate Scope
2.7 Unsuccessful Substrates
2.8 Addition of Radical Scavenger
2.9 The Role of AlMe3 as a Base
2.10 Stoichiometric Experiments
2.11 Kinetic Isotope Effect Experiments
2.12 Conclusion
2.13 Experimental
References
3 Development of a Synthetic Method for Tridentate Phosphine Ligands
3.1 Introduction
3.2 Selective Formation of Phenoxydiarylphosphine
3.3 Synthesis of Tridentate Phosphine Ligands
3.4 Modulation of All of the Aryl Groups
3.5 Conclusion
3.6 Experimental

5 Iron-Catalyzed Oxidative C-H Alkenylation of Thiophenes with Enamines
5.1 Introduction
5.2 Reaction Design and Initial Results
5.3 Reaction Kinetics
5.4 Investigation of Reaction Parameters
5.5 Effect of Ligand
5.6 Substrate Scope
5.7 Copolymerization
5.8 EZ Isomerization
5.9 Deuterium Labeling Experiments
5.10 Kinetic Isotope Effect Experiments
5.11 Conclusion
5.12 Experimental
References
6 Conclusions and Perspectives