studies on synthesis of polycyclic aromatic …polycyclic aromatic hydrocarbons (pahs) 4 pah...
TRANSCRIPT
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指導教員 市川淳士
ジフルオロカルボカチオンの発生を基盤とする
多環式芳香族炭化水素の合成研究
Studies on Synthesis of Polycyclic Aromatic
Hydrocarbons Based on Difluorocarbocation
Generation
発表者 高尾 豪
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2Table of Contents
Chapter 2 Synthesis of PAHs Based on CH3-Arenes via
Domino Cyclization of Difluoroalkenes
Chapter 1 General Introduction
Chapter 3 Synthesis of Substituted Acenes via
Domino or Stepwise Cyclizations from 2-
CF3 Alkenes
Chapter 4 Synthesis of CHF2-Naphthalenes from 1,1-
Difluoroallenes via Pd-Catalyzed Insertion
Chapter 5 Conclusions
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3Table of Contents
Chapter 2 Synthesis of PAHs Based on CH3-Arenes via
Domino Cyclization of Difluoroalkenes
Chapter 1 General Introduction
Chapter 3 Synthesis of Substituted Acenes via
Domino or Stepwise Cyclizations from 2-
CF3 Alkenes
Chapter 4 Synthesis of CHF2-Naphthalenes from 1,1-
Difluoroallenes via Pd-Catalyzed Insertion
Chapter 5 Conclusions
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4Polycyclic Aromatic Hydrocarbons (PAHs)
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5PAH Synthesis: Single Ring Construction
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6PAH Synthesis: Multiple Ring Construction
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7Plans for PAH Synthesis
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8Table of Contents
Chapter 2 Synthesis of PAHs Based on CH3-Arenes via
Domino Cyclization of Difluoroalkenes
Chapter 1 General Introduction
Chapter 3 Synthesis of Substituted Acenes via
Domino or Stepwise Cyclizations from 2-
CF3 Alkenes
Chapter 4 Synthesis of CHF2-Naphthalenes from 1,1-
Difluoroallenes via Pd-Catalyzed Insertion
Chapter 5 Conclusions
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9Previous Work: SNV-Type Domino Cyclization
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10Previous Work: 1,1-Difluoro-1-alkene Preparation
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11Chapter 2: CH3-Arene-Based PAH Synthesis
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12CH3-Arene-Based PAH Synthesis
4 Ar1 Ar2 Ar3 Ar4 Ar5
Ar1
Ar2
Ar3
Ar4
Ar5
対称PAH
非対称PAH
5種類 ⇒ 計15種類
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13Introduction of 1st Aryl Groups
1st 2nd
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14Preparation of Benzyl Bromides
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15Benzylation of CF3-Allyl Silane
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16Benzylation of CF3-Allyl Silane
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17Preparation of 2-Trifluoromethyl-1-alkenes
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18Introduction of 2nd Aryl Groups
1st 2nd
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19Preparation of 1,1-Difluoro-1-alkenes (1)
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20Preparation of 1,1-Difluoro-1-alkenes (1)
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21Generation of Benzyl Lithiums
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22Stannylation of Benzyl Bromides
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23Preparation of 1,1-Difluoro-1-alkenes (2)
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24Domino Cyclization of 1,1-Difluoro-1-alkenes (1)
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25Plausible Reaction Mechanism
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26Domino Cyclization of 1,1-Difluoro-1-alkenes (2)
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27PAH Synthesis by Dehydrogenation
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28Summary: Chapter 2
Bull. Chem. Soc. Jpn. 2019, 92, 2019.
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29Table of Contents
Chapter 2 Synthesis of PAHs Based on CH3-Arenes via
Domino Cyclization of Difluoroalkenes
Chapter 1 General Introduction
Chapter 3 Synthesis of Substituted Acenes via
Domino or Stepwise Cyclizations from 2-
CF3 Alkenes
Chapter 4 Synthesis of CHF2-Naphthalenes from 1,1-
Difluoroallenes via Pd-Catalyzed Insertion
Chapter 5 Conclusions
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30Structures and Properties of Substituted Acenes
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31Chapter 3: Synthesis of Substituted Acenes
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32Domino Cyclization: SN1’ + SNV-type Reaction
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33Domino Cyclization: SN1’ + SNV-type Reaction
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34Domino Cyclization and Dehydrogenation
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35Stepwise Cyclization
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36Stepwise Cyclization
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37Stepwise Cyclization
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38Stepwise Cyclization
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39First Cyclization: SN1’ Reaction
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40Second Cyclization: SNV-Type Reaction
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41Second Cyclization: SNV-Type Reaction
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42Installation of Substituents and Dehydrogenation
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43Installation of Substituents and Dehydrogenation
Method A
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44Installation of Substituents and Dehydrogenation
Method B
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45Oxidative Cation Generation from Difluoroalkenes
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46Oxidative Cation Generation from Difluoroalkenes
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47Installation of Substituents
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48Summary: Chapter 3
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49Oxidative Cation Generation from CHF2-Arenes
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50Table of Contents
Chapter 2 Synthesis of PAHs Based on CH3-Arenes via
Domino Cyclization of Difluoroalkenes
Chapter 1 General Introduction
Chapter 3 Synthesis of Substituted Acenes via
Domino or Stepwise Cyclizations from 2-
CF3 Alkenes
Chapter 4 Synthesis of CHF2-Naphthalenes from 1,1-
Difluoroallenes via Pd-Catalyzed Insertion
Chapter 5 Conclusions
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51Utility of CHF2-Arenes
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52Conventional Syntheses of CHF2-Arenes
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53Plan for CHF2-Naphthalenes
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54Plan for CHF2-Naphthalenes
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55Optimization of Conditions: Ligands
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56Optimization of Conditions: Ligands
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57Optimization of Conditions: Ligands
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58Optimization of Conditions: Ligands
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59Synthesis of CHF2-Naphthalenes
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60Plausible Reaction Mechanism
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61Tsuji-Trost Reaction of Difluorinated p-Allyl-Pd
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62Summary: Chapter 4
Org. Biomol. Chem. 2019, 17, 5047.
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63Conclusion
Bull. Chem. Soc. Jpn. 2019, 92, 2019.
Org. Biomol. Chem. 2019, 17, 5047.
In Preparation
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64
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65
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66Electronic Effects of Fluorine Substituents
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67Utility of Fluorine Substituents: Materials
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68Utility of Fluorine Substituents: Materials
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69Preparation of CH3-Arenes
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70Skeletal Rearrangement
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71Structure and Properties of Acenes (Linear PAH)
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72Pinpoint-Fluorinated Acenes
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73Synthesis of Substituted Acenes
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74Dehydrogenation
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75Screening of Lewis Acids
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76Screening of Lewis Acids
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77Proposed Mechanism
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78Generation of Carbonyl Groups