Sustainable and Functional Redox Chemistry

Cover
Half Title
Green Chemistry Series
Sustainable and Functional Redox Chemistry
Copyright
Preface
Contents
Part 1. Sustainable Redox Reaction
	1. Redox-mediated Electrochemical Cyclization Reactions
		1.1 Introduction
		1.2 Radical Cyclization Reactions
			1.2.1 Cyclization Reactions of Heteroatom-centered Radicals
			1.2.2 Cyclization Reactions of Carbon-centered Radicals
		1.3 Halide-mediated Ionic Cyclization Reactions
		1.4 Conclusion
		Acknowledgements
		References
	2. Recent Advances in the Kolbe and Non-Kolbe Electrolysis of Carboxylic Acids
		2.1 Intriduction
		2.2 Background of the Kolbe Electrolysis
		2.3 Background of Non-Kolbe Electrolysis
		2.4 Recent Advances in the Electrolysis of Carboxylic Acids
			2.4.1 Kolbe Intramolecular Cyclisation
				2.4.1.1 Limitations of the Method
			2.4.2 Hofer–Moest Synthesis of Isocyanates
			2.4.3 Hofer–Moest Synthesis of Orthoesters
			2.4.4 Electrochemical Methoxylation
			2.4.5 Electrochemical Decarboxylation of Malonic Acid Derivatives
		2.5 Recent Advances in the Electrolysis of Carboxylic Acid Derivatives
			2.5.1 Electrochemical Deprotection of Aromatic Esters
			2.5.2 Electrochemical Deoxygenation of Diphenylphosphinates
		2.6 Future Perspectives
		2.7 Conclusion
		Abbreviations
		Acknowledgements
		References
	3. Novel Electrolytic Processes
		3.1 Introduction
		3.2 Parallel Batch Systems Used for Electroorganic Synthesis
			3.2.1 Parallel Batch Systems Using the Cation Pool Method
			3.2.2 Parallel Batch Processes for Electrosynthesis
		3.3 Combinatorial Flow System for Electroorganic Chemistry
			3.3.1 Flow Electrochemistry
			3.3.2 PEM Reactor
		3.4 Bipolar Electrochemical System
		3.5 Conclusion
		References
	4. A Sugar Machiney
		4.1 Introduction
		4.2 Electrochemical Generation of Glycosylation Intermediates
			4.2.1 Generation of Glycosyl Triflate Intermediates
			4.2.2 Generation of Glycosyl Sulfonium Ion Intermediates
		4.3 Development of a Method for Automated Electrochemical Solution-phase Synthesis of Oligosaccharides
			4.3.1 Proof of Principle of One-pot Iterative Glycosylation
			4.3.2 Demonstration of Automated Electrochemical Assembly of Oligosaccharides
		4.4 Synthesis of Biologically Active Oligosaccharides
			4.4.1 Synthesis of TMG-chitotriomycin
			4.4.2 Synthesis of Myc-LCOs
		4.5 Synthesis of 1,2-trans Glycosidic Linkages of Hexoses via Automated Electrochemical Assembly
		4.6 Synthesis of Cyclic Oligosaccharides via Automated Electrochemical Assembly
		4.7 Conclusion
		Acknowledgements
		References
		Part 2 Sustainable Redox Catalysis
Part 2. Sustainable Redox Catalysis
	5. Vanadium(V)-induced Oxidative Cross-coupling of Enolate Species
		5.1 Introduction
		5.2 Oxovanadium(V)-induced Intermolecular Selective Oxidative Cross-coupling between Boron and Silyl Enolates
		5.3 Oxidative Cross-coupling between Various Boron and Silyl Enolates
		5.4 Oxovanadium(V)-catalyzed Oxidative Cross-coupling between Boron and Silyl Enolates under O2 as a Terminal Oxidant
		5.5 Conclusion
		Abbreviations
		Acknowledgements
		References
	6. Mediated Electron Transfer in Electrosynthesis: Concepts, Applications, and Recent Influences from Photoredox Catalysis
		6.1 Introduction
		6.2 Concepts and Applications
			6.2.1 Direct and Indirect Electrosynthesis
			6.2.2 The Catalytic Current
			6.2.3 Redox Catalysis and Chemical Catalysis
			6.2.4 In-cell- and Ex-cell-mediated
		6.3 Approaches Toward Facilitating Mediator Recycling
			6.3.1 Ionically Tagged Mediators
			6.3.2 Polymediators
			6.3.3 Mediator-modified Electrodes
		6.4 Mediators in Photoelectrochemical Synthesis
			6.4.1 Transformations at Photoelectrodes
			6.4.2 Sequential Activation of Substrates by Electro- and Photochemistry
			6.4.3 Enhancing Mediator Reactivity with Light
		6.5 Conclusions
		Acknowledgements
		References
	7. Synergy of Electrochemistry and Asymmetric Catalysis
		7.1 Introduction
		7.2 Substrates as the Redox Entities in Electrochemical Asymmetric Catalysis
		7.3 Catalysts as Redox Entities in Electrochemical Asymmetric Catalysis
		7.4 Both Substrates and Catalysts as the Redox Entities in Electrochemical Asymmetric Catalysis
		7.5 Conclusion
		Acknowledgements
		References
	8. Alternative Approaches for Scalable Artificial Photosynthesis via Sustainable Redox Processes
		8.1 Introduction
		8.2 Nonfood Biomass Oxidation
			8.2.1 Photocatalytic Nonfood Biomass Oxidation
			8.2.2 Electrocatalytic and Photoelectrocatalytic Nonfood Biomass Oxidation
		8.3 Synthetic Polymer Oxidation
			8.3.1 Heterogeneous Photocatalytic Oxidation of Synthetic Polymers
			8.3.2 Homogeneous Photocatalytic Oxidation of Synthetic Polymers
		8.4 Photosynthetic and Photocatalytic Reduction by Metal Halide Perovskites
		8.5 Conclusions and Outlook
		Acknowledgements
		References
	9. Bioinspired Catalyst Learned from B12-dependent Enzymes
		9.1 Introduction
			9.1.1 B12 (Cobalamin)-dependent Enzymes
			9.1.2 Catalyst Design for B12-dependent Enzyme-inspired Reactions
		9.2 Photo-driven Molecular Transformation
			9.2.1 Heterogeneous Catalyst System
			9.2.2 Esters and Amides Formation Coupled with Dehalogenation
			9.2.3 Visible Light-driven Catalytic System
			9.2.4 B12-inspired Hydrogen Production and Alkene Reduction
			9.2.5 Homogeneous Catalyst System
			9.2.6 Cross-coupling Reactions
			9.2.7 B12–BODIPY Dyad System
			9.2.8 Catalysis of B12 Without Photocatalyst
		9.3 Summary and Outlook
		Acknowledgements
		References
Part 3. Functional Redox System
	10. Redox-active Molecules and Their Energy Device Application
		10.1 Introduction
		10.2 Organic Active Materials for Li-ion Batteries
			10.2.1 Basic Concepts
			10.2.2 Capacity Increase
			10.2.3 Cyclability Increase
			10.2.4 Voltage Increase
		10.3 Organic Active Materials for Redox Flow Batteries
			10.3.1 Aqueous Electrolyte
			10.3.2 Nonaqueous Electrolyte
		References
	11. Redox-active Polymeric Materials
		11.1 Introduction
		11.2 Conjugated Polymers
			11.2.1 Doping of Conjugated Polymers
			11.2.2 Oxidative and Reductive Electropolymerization
			11.2.3 Electrochemical Polymer Reaction
			11.2.4 Two- and Three-dimensional Conjugated Polymers
		11.3 Nonconjugated Polymers with Redox-active Units
			11.3.1 Polymers with Redox-active Units in the Side Chain
			11.3.2 Block Copolymers with Redox-active Units
			11.3.3 Polymeric Materials Mimicking Metalloproteins
			11.3.4 Redox Units at the Periphery of Dendrimers
			11.3.5 Redox-active Inorganic Polymers
		11.4 Conjugated Polymers with Redox-active Moieties
		11.5 Conclusion
		References
	12. Chiral Metal Electrodes for Enantioselective Analysis, Synthesis, and Separation
		12.1 Background
		12.2 Elaboration of Chiral Metal Electrodes
			12.2.1 Adsorption of Chiral/Achiral Molecules on Metal Surfaces
			12.2.2 Binding of Chiral Ligands to Metal Surfaces
			12.2.3 Controlled Cutting of Bulk Metals
			12.2.4 Chiral Molecular Imprinting
		12.3 Applications of Chiral Metal Electrodes
			12.3.1 Enantioselective Analysis
			12.3.2 Asymmetric Synthesis
			12.3.3 Electrochemical Separation
		12.4 Conclusion and Perspectives
		Acknowledgements
		References
	13. Fluorescent Sensors for Water
		13.1 Introduction
		13.2 PET-based Fluorescent Sensors
		13.3 PET/FRET-based Fluorescent Sensors
		13.4 PET/AIEE-based Fluorescent Sensors
		13.5 SFC/AIEE-based Fluorescent Sensors
		13.6 ICT-based Fluorescent Sensors
		13.7 Fluorescent Sensor-doped Polymer Films
		13.8 Conclusion
		Acknowledgements
		References
	14. Photoredox Chemistries of Cyclometalated Ir(III) Complexes
		14.1 Photoinduced Electron Transfer of Cyclometalated Ir(III) Complex
		14.2 Electronic Structures of Cyclometalated Complexes of Ir(III)
		14.3 Sensory Applications of Intramolecular Photoinduced Electron Transfer of Ir(III) Complexes
		14.4 Photoredox Catalysis Based on Intermolecular Photoinduced Electron Transfer of Ir(III) Complexes
		14.5 Outlook
		Acknowledgements
		References
	15. Electrogenerated Chemiluminescence in Functional Redox Chemistry
		15.1 Introduction
		15.2 Fundamentals of ECL: Mechanisms of Light Generation
			15.2.1 Annihilation ECL
			15.2.2 Coreactant ECL
		15.3 Applications of ECL in Molecular Electrochemistry
			15.3.1 Novel ECL Reaction Systems
			15.3.2 ECL for Imaging Applications
			15.3.3 ECL of Organic Systems
			15.3.4 Aggregation and Crystallization-induced Emission in ECL
		15.4 Conclusions and Future Directions
		Acknowledgements
		References
Subject Index