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Title Page

Contents

Abstract 9

List of Abbreviations 11

Chapter 1. Introduction 14

1.1. Sustainable Photoreaction in Organic Chemistry 14

1.2. Synthesis of Cyclobutane Scaffold via Visible Light 17

1.3. The Importance of Sulfonyl Fluorides as 'Click' Chemistry 20

1.4. Synthesis of β-Aryl Ethenesulfonyl Fluorides 21

1.5. Unique Reactivity of 'on-Water' System 24

1.6. Notable Compounds, Benzofuran and Benzothiophene 26

Chapter 2. Synthesis of Visible Light-mediated Aquacatalytic Intermolecular [2 + 2] Cycloadducts 28

2.1. Introduction 28

2.2. Screening of Reaction Medium 30

2.3. Equivalent Comparison 32

2.4. Optimization of Photocatalyst 33

2.5. Screening of Light Source 36

2.6. Substrate Scope 37

2.7. Applications of [2 + 2] Cycloadducts 45

2.8. Mechanism study 47

Chapter 3. Conclusion 58

Chapter 4. Experimental Section[원문불량;p.106-107] 59

Reference. 154

논문요약 168

List of Tables

Table 2-1. Screening of the reaction medium 31

Table 2-2. Equivalent Comparison 32

Table 2-3. Comparison of catalytic amounts of 4Cz-IPN 33

Table 2-4. Screening of photocatalyst 34

Table 2-5. Screening of the light sources 36

List of Figures

Figure 1-1. Representative visible-light mediated organic reactions 16

Figure 1-2. Selected cyclobutane compounds having bioactivities 17

Figure 1-3. Reaction mechanism of [2 + 2] photocycloaddition. 19

Figure 1-4. The concept of click chemistry 20

Figure 1-5. Synthesis of β-aryl ESF 23

Figure 1-6. Example of 'on-water' reaction and reaction mechanism. 25

Figure 1-7. Various bioactive compounds beaing benzofuran and benzothiophene scaffolds 27

Figure 2-1. Chemical structure of photocatalysts and their T₁ energies 35

Figure 2-2. Substrate scope of β-aryl ESF with benzofuran 39

Figure 2-3. Substrate scope of β-aryl ESF with benzothiophene 40

Figure 2-4. Substrate scope of various alkenes 41

Figure 2-5. Substrate scope of β-aryl nitroolefin 42

Figure 2-6. Limitations of reaction 44

Figure 2-7. Application of the [2 + 2] cycloadducts 46

Figure 2-8. Control experiments 48

Figure 2-9. UV-vis spectra 51

Figure 2-10. PL spectra of the reaction components 52

Figure 2-11. Normalized PL spectra 53

Figure 2-12. Stern-Volmer plot 54

Figure 2-13. Investigation of 'on-water' effect 56

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