創新性高效率串連合成具有3號位和2及4號位取代之碲、硒雜芳香環化合物

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研究生：	瓦奇 Karapala, Vamsi Krishna
論文名稱：	創新性高效率串連合成具有3號位和2及4號位取代之碲、硒雜芳香環化合物 Unprecedented, Cascade and Effective Syntheses of 3-Substituted and 2,4-Disubstituted Tellurophenes and Selenophenes
指導教授：	韓建中 Han, Chien-Chung
口試委員:	陳貴通 Tan, Kui-Thong 蔡易州 Tsai, Yi-Chou 許銘華 Hsu, Ming-Hua 李志聰 Lee, Jyh-Tsung
學位類別：	博士 Doctor
系所名稱：	理學院 - 化學系 Department of Chemistry
論文出版年：	2019
畢業學年度：	107
語文別：	英文
論文頁數：	342
中文關鍵詞：	碲雜芳香環化合物、硒雜芳香環化合物
外文關鍵詞：	Tellurophenes, Selenophenes
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迄今，由於製備重硫族吩 (硒吩及碲吩)之已知方法不易及困難，如何能有效的合成出重硫族吩仍是一尚未被廣泛探索的領域。論文首先詳述以2-乙炔基-2-烷基環氧乙烷為骨架合成含3號位取代的碲吩；接著，以另一骨架1,1-二溴-1-烯-3-炔含3號位及2和4號位取代的碲吩及硒吩，最後則以系統性回顧近十年以碲吩為主題的文獻作結。
論文第一章節簡介重硫族吩的歷史脈絡及提供和本論文研究相關的背景介紹。第二章節敘述系統性製備含3號位及2和4號位取代的碲吩及硒吩。透過一系列串聯反應，從還原脫溴、碲氫化、親核環化到芳香化，含各式取代的1,1-二溴-1-烯-3-炔以對應的硫族鹽類被溫和且高產率地轉化為單取代及雙取代的碲吩及硒吩。實驗結果顯示在反應中生成之碲鹽的反應性強烈地被溶劑系統極性及烯炔反應物上的取代基的電子性質影響。本方法為第一個報導在室溫下能保有高產率並得到3-芳基碲吩的研究，且為一個可得到多取代碲吩及硒吩的甚佳路徑。

With very limited and difficult synthetic routes for making heavier chalcogenophenes (selenophenes and tellurophenes), effective synthesis of heavier chalcogenophenes is a largely unexplored area of interest. This thesis details firstly systematic approach to synthesize 3-substituted tellurophenes from 2-ethynyl-2-alkyloxiranes. Secondly, synthetic approaches to 3-substituted and 2,4-di-substituted tellurophenes and selenophenes from various 1,1-dibromo-1-en-3-ynes. Finally, well organized literature survey of tellurophenes in this decade.
The first chapter provides an introduction to the history of the field of heavier chalcogenophenes as well as context for the work presented in this thesis. The second chapter describes a systematic approach to synthesize 3-substituted and 2,4-substitued tellurophenes and selenophenes. Substituted 1,1-dibromo-1-en-3-ynes are smoothly converted to mono- and di-substituted tellurophenes and selenophenes with the corresponding chalcogenide salts in high yields via a series of cascade reactions through reductive debromination, hydrotelluration, nucleophilic cyclization, and aromatization. Close inspection of the results clearly showed that the reactivity of in situ prepared telluride salts is significantly influenced by the polarity of the solvents and the electronic nature of the substituent on the enyne substrate. This method reports the first direct synthesis of 3-aryltellurophenes in high yields at room temperature. This novel reaction strategy is also found to be a promising synthetic method for multisubstituted tellurophenes and selenophenes.

Table of Contents

Abstract    i
Abstract (Chinese)    ii
Acknowledgements    iii
Table of Contents    iv
List of Tables    vii
List of Schemes    viii
List of Figures    ix
List of Appendices    x
List of Abbreviations    xi
Chapter 1:  Overview of Heavier Chalcogenophenes (Selenophenes and Tellurophenes)    1
1 Introduction    1
2 Structure and Bonding in Chalcogenophenes    1
3 Spectroscopy of Chalcogenophenes    4
3.1 Vibrational Spectroscopy    4
3.2 1H NMR Spectroscopy    5
3.3 13C NMR Spectroscopy    6
3.4 77Se and 125Te NMR Spectroscopy    7
4 Effect of Heavier Chalcogenophenes    7
4.1 Optoelectronic Properties    7
4.2 Biological Properties    13
5 Thesis Scope    14
6 References    15
Chapter 2: Synthesis of Functionalized Heavier Chalcogenophenes    17
1 Introduction    17
1.1 Existing Synthetic Routes to Tellurophenes    17
2 Results and Discussion    22
2.1 Synthesis of 3-Substituted Tellurophenes    22
2.2 Mechanistic Rationalization for 3-Substituted Tellurophenes    29
2.3 Substrate Scope Study for 3-Substituted Tellurophenes    30
2.4 Synthesis of 2,4-Substituted Tellurophenes    33
2.5 Substrate Scope Study for 2,4-Substituted Tellurophenes    35
2.6 Mechanistic Implications for Substituted Tellurophenes    40
2.7 DFT Calculations    41
2.8 Synthesis of Substituted Selenophenes    43
3 Conclusions    45
4 Experimental Section    45
4.1 General Information    45
4.2 Synthesis and Analytical Data of 2-Ethynyl-2-alkyloxiranes    46
4.3 Synthesis and Analytical Data of 1,1-Dibromo-1-en-3-ynes    50
4.4 Synthesis and Analytical Data of 3-Substituted Tellurophenes    60
4.5 Synthesis and Analytical Data of 2,4-Disubstituted Tellurophenes    66
4.6 Synthesis and Analytical Data of Substituted Selenophenes    75
5 References    79
Chapter 3: Preface    81
Chapter 3: Review of Tellurophenes    82
1 Introduction    82
2 Theoretical Methods    82
3 Experimental Structural Methods    87
3.1 Molecular Structure    87
3.2 Molecular Spectroscopy    91
4 Thermodynamic Aspects    100
5 Reactivity    104
5.1 Thermal and Photochemical Reactions    104
5.2 Substitutions at Tellurium    106
5.3 Electrophilic Substitutions    108
5.4 Reactions with C-Anion Equivalents    109
5.5 Organometallic Reactions    112
5.6 Reactivity of Substituents Attached to Ring Carbon Atoms    117
5.7 Microwave Reactions    118
5.8 Polymerization Reactions    118
5.9 Extrusion of Tellurium    123
6 Ring Synthesis    124
6.1 Ring Synthesis from Acyclic Compounds    124
6.2 Ring Synthesis from Cyclic Compounds    130
7 Important Compounds and Applications    131
7.1 Compounds with Applications in Biological Science    131
7.2 Compounds with Applications in Material Science    132
8 References    135
Appendix A: NMR Spectra    140
Appendix B: Mass Spectra 273
Appendix C: Crystal Structure Data 327


                                

Chapter 1

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Chapter 3
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