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
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
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