Photochemical and Electrochemical Activation Strategies of C(sp3)-Based Building Blocks for Organic Synthesis

Cover
Springer Theses Series
Photochemical and Electrochemical Activation Strategies of C(sp3)-Based Building Blocks for Organic Synthesis
Copyright
Supervisor’s Foreword
Preface
Contributions
Acknowledgments
Contents
List of Figures
List of Schemes
List of Tables
Part I. C(sp2)–C(sp3) Bond Formation Reactions Enabled by Photoredox/Nickel Dual Catalysis
	1. The Key Concepts and Strategy in Photoredox/Nickel Dual Catalysis and Application to C–C Bond Formation Reactions
		1.1 Introduction
		1.2 Key Concepts in Visible Light Photoredox Catalysis
		1.3 Principles of Photoredox/Nickel Dual Catalysis
		1.4 Photocatalytic C–H Activation and the Role of Chlorine Radicals
		1.5 Conclusion
		References
	2. Highly Regioselective and E/Z‑Selective Hydroalkylation of Alkyne via Photoredox-Mediated Ni/Ir Dual Catalysis
		2.1 Introduction
		2.2 Results and Discussion
			2.2.1 Optimization of Reaction Conditions
			2.2.2 Substrate Scope
			2.2.3 Post-Functionalization and Mechanistic Studies
		2.3 Conclusion
		2.4 Experimental Section
			2.4.1 General Information
			2.4.2 Substrate Preparation
			2.4.3 Reaction Optimization
			2.4.4 Identification of α/β- and E/Z Configuration of Products
			2.4.5 General Procedure for the Hydroalkylation of Activated Alkynes
			2.4.6 A Representative 1 mmol Scale Reaction
			2.4.7 Post-Functionalization of Enone Products
			2.4.8 Radical Quenching Study Using TEMPO
			2.4.9 Investigation of Regioselectivity Dependence on the Size of Coupling Partner
			2.4.10 Investigation of a Base Effect
			2.4.11 Alkenylation Test of THF Radicals by DTBP
			2.4.12 Deuterium Labeling Study
		References
Part II. Development of C(sp3)–Heteroatom Bond-Forming Reactions via Electrochemical Activation of C(sp3)–B Bonds and Follow-Up Projects
	3. Recent Achievements of C(sp3)‒Heteroatom Bond Formation in Electroorganic Synthesis and History of C(sp3)‒B Bond Activation
		3.1 Introduction
		3.2 Advances in the Merger of Electrochemistry and Organic Synthesis
			3.2.1 Introduction of Electrosynthesis
			3.2.2 Representative Electrocatalytic Reactions
		3.3 History of C(sp3)−B Bond Activation
		3.4 Conclusion
		References
	4. Introduction of Heteroatoms to Alkyl Carbocations Generated from Alkylboron Reagents via Electrochemical Activation
		4.1 Introduction
		4.2 Results and Discussion
		4.3 Conclusion
		4.4 Experimental Section
			4.4.1 General Information
			4.4.2 Substrate Preparation
			4.4.3 Electrochemical Analyses for Reaction Design
			4.4.4 Reaction Optimization
			4.4.5 General Procedure for Electrochemical C(sp3)–Heteroatom Bond Formation
			4.4.6 Representative Larger Scale Reactions
			4.4.7 Experimental Procedure for Electrochemical Bond Formation via In Situ Generation of Reactive Precursor
			4.4.8 Divided Cell Experiments
			4.4.9 Constant Potential Electrolysis
			4.4.10 Mechanistic Probes and Kinetic Study
			4.4.11 Experimental Procedures and Characterization Data
			4.4.12 Unsuitable Trifluoroborate Substrates and Heteroatom Nucleophiles
			4.4.13 X-Ray of Compound of (11S)-87
		References