鈀催化的異構化和內酯化

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李諾珠(Le Thi Ngoc Chuc) 查詢紙本館藏

畢業系所

化學學系

論文名稱

鈀催化的異構化和內酯化
(Palladium Catalyzed Isomerization and Lactonization)

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至系統瀏覽論文 (2025-4-1以後開放)

摘要(中)

本文的工作分為兩章。在第一章中，使用鈀（0）納米粒子實現了 2-alkenylbenzoic acid 衍生物的異構化以生成（E）-烯烴。該反應的範圍包括羧酸，酯和醯胺，並能耐受苯環上的各種取代基。異構化反應由可回收的 Pd(0) 納米顆粒催化，該顆粒由 PdCl2 原位制備，並通過 X 射線粉末衍射和掃描電子顯微鏡分析進行表征。 1H NMR 研究和動力學建模支持逐步過程。該新方法被用于高效合成天然二氫異香豆素。

在第二章中，討論了合成的鄰苯二甲酸酯化合物。用 1,2-bis(phenylsulfinyl)ethane palladium(II) acetate (White catalyst) 氧氣在 DMSO 中實現 2-allylbenzoic acids (1) 的烯丙基氧化生成 3-ethylidenephthalides (3) 或 3-vinylphthalides (4) 在堿性條件或酸性條件下。將反應條件應用於各種取代的 2-allylbenzoic acids。還討論了該反應的機理。

摘要(英)

The work presented in this thesis has been divided into two chapters. In chapter one, isomerization of 2-alkenylbenzoic acid derivatives to give (E)-alkenes was achieved with palladium(0) nanoparticles. The scope of this reaction includes carboxylic acid, ester, and amides and tolerates various substituents on the benzene ring. This isomerization reaction was catalyzed by recyclable Pd(0) nanoparticles, prepared in situ from PdCl2 and characterized by X-ray powder diffraction and scanning electron microscopy analyses. 1H NMR studies and kinetic modeling supported a stepwise process. This new process was applied to synthesize a natural dihydroisocoumarin with good efficiency.

In chapter two deals with the phthalide compounds synthesised. Allylic oxidation of 2-allylbenzoic acids (1) to give 3-ethylidenephthalides (3) or 3-vinylphthalides (4) was achieved with 1,2-bis(phenylsulfinyl)ethane palladium(II) acetate (White catalyst), oxygen in DMSO under the basic condition or the acidic conditon. The reaction conditions were applied to various substituted 2-allylbenzoic acids. The mechanism of this reaction is also discussed.

關鍵字(中)

★ 鈀催化劑
★ 異構化
★ 漆膜化

關鍵字(英)

★ palladium catalyst
★ Isomerization
★ Lactonization

論文目次

Table of Contents

Abstract i
Acknowledgements ii
Table of Contents iii
List of Tables v
List of Figures vi
List of Schemes vii
List of Appendix for chapter one viii
List of Appendix for chapter two xiii
List of Symbols and Abbreviations xvii
Chapter One: 1
Palladium catalyzed Isomerization of 2-Alkenylbenzoic Acids 1
1.1 Introduction 1
1.2 Isomerization of benzene containing olefins 2
1.2.1 Allylbenzene isomerization reaction 2
1.2.2 Base-assisted “Carbon-Claisen” rearrangement of 4-phenyl-1-butene 2
1.2.3 Palladium catalyzed isomerization of alkenes: a pronounced influence of an o-phenol hydroxyl group 3
1.3 The reaction was carried out with 2- (3-butene)benzoic Acid 1a 6
1.4. Optimization of reaction conditions 8
1.5 Results and discussions 10
1.5.1 Isomerization of Substituted 2-(3-Butenyl)benzoic Acids 10
1.5.2 Isomerization of 2-Alkenylbenzoic Acids 12
1.5.3 Monitor the reaction 14
1.5.4 Recycling studies for the isomerization reaction of 1a 17
1.5.5 Isomerization reactions catalyzed by various Pd sources 18
1.5.6 New synthesis of dihydroisocoumarin 33 19
1.6 Summary 20
1.7 References 20
Chapter Two: 23
Palladium catalyzed Allylic Oxidation and Lactonization of 2-Allylbenzoic Acids 23
2.1 Introduction 23
2.2 Literature reviews 23
2.3 Results and discussions 26
2.3.1 Optimization of reaction conditions 26
2.3.2 Allylic oxidation of substituted 2-allylbenzoic Acids 30
2.3.3 Synthesis of 3-ethyl-6-hydroxyphthalide (6) 32
2.3.4 Mechanistic experiments 33
2.4 Summary 37
2.5 References 37
3. Experimental section for chapter one 41
3.1 General procedure for the Pd-catalyzed isomerization of o-Alkenylbenzoic acids. 41
3.2 Synthesis of Dihydroisocoumarin 33 57
3.3 References 60
4. Experimental section for chapter two 62
4.1 Synthesis of 2-Alkenylbenzoic Acids 62
4.2 General procedure for the White catalyst lactonization of 2-allylbenzoic Acids. 63
4.3 Synthesis of 3-Ethyl-6-hydroxyphthalide (6) 74
4.4 Synthesis of compound 1-D2 75
4.5 Kinetic Isotope Effect (KIE) 79
4.5.1 Procedure for kinetic isotope effect 79
4.5.2 Starting material 1 + 1 N NaOH 79
4.5.3 Starting material 1-D2 + 1 N NaOH 82
4.5.4 Kinetic isotope effect in the basis condition 84
4.5.5. Starting material 1 + 1 N HCl 84
4.6 References 88
Appendix for chapter one 82
Appendix for chapter two 191

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指導教授

侯敦仁

審核日期

2020-3-31

推文