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研究生： 帕卡許
Prakash, Sekar
論文名稱： 碳-氫鍵活化應用於銠金屬催化烯基化反應及鈷金屬催化氧化環化反應
Rhodium-Catalyzed Alkenylation and Cobalt-Catalyzed Oxidative Cyclization Reactions via C–H Bond Activation
指導教授： 鄭建鴻
Cheng, Chien-Hong
口試委員: 劉瑞雄
Liu, Rai-Shung
蔡易州
Tsai, Yi-Chou
莊士卿, 謝仁傑
Chuang, Shih-Ching, Hsieh, Jen-Chieh
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： 2017
畢業學年度： 105
語文別： 英文
論文頁數： 283
中文關鍵詞： 銠 、鈷 、C-H 活化 、環化 、烯基化 、beta-氫消除反應
外文關鍵詞： Rhodium, Cobalt, C-H Activation, Annulation, Alkenylation, beta hydride elimination
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    • 摘要
    在本論文中，描述了銠催化鄰烯基化反應和鈷催化氧化環化反應。為了方便和更容易理解，本論文分為三章。 第一章描述了銠催化的鄰位乙烯化反應，而第二和第三章分別描述了鈷催化芳烴與炔烴進行氧化環化反應和酚基導引銠催化醛基碳-氫鍵活化並進行烯基化反應。
     第一章描述以N-甲氧基苯甲酰胺利用銠(III)催化碳-氫鍵活化並與乙烯基錫烷進行鄰位乙烯基化反應。此反應推測經由碳-氫鍵活化，繼而進行乙烯基錫烷的轉移金屬化和還原消除，而得到高產率的鄰乙烯基酰胺

     第二章討論一系列以2-苯基芳烴、偶氮苯、2-乙烯基吡啶和亞胺類化合物與炔類化合物利用較便宜的鈷金屬進行催化氧化環化反應，並分別得到不同高產率的季銨鹽。

     第二章討論以水楊醛之酚基導引銠催化醛基碳-氫鍵活化並與亞甲基環丙烷反應合成甲酰碳-氫鍵烯基化產物。有趣地是推電子基和拉電子基取代之水楊醛在此反應中提供了不同的選擇性。

    ABSTRACT
    In this thesis, rhodium catalyzed ortho-alkenylation reactions and cobalt catalyzed oxidative annulation reactions are described. For convenience and better understanding, the thesis is divided into three chapters. The first chapter describes the rhodium catalyzed ortho vinylation reactions and the second and third chapter describes the CoCp* catalyzed oxidative annulation of arenes with alkynes and rhodium catalyzed –OH assisted formyl C–H alkenylation reactions respectively.
     Chapter 1 describes the ortho-vinylation reactions of N-methoxy benzamides with vinyl stannanes via Rh(III) catalyzed C-H activation reactions. This reaction proceeds via C–H activation followed by transmetallation of vinyl stannane and reductive elimination afford ortho-vinyl amides in high yields.

     Chapter 2 deals inexpensive cobalt catalyzed oxidative annulation of 2-phenylarenes, azobenzenes, 2-vinyl pyridines and imines with internal alkynes provides a variety of quaternary ammonium salts in high yields.

     Chapter 3 deals with rhodium catalyzed –OH assisted formyl C–H activation of salicylaldehydes with methylenecyclopropane provides formyl C–H alkenylation products. Interestingly, electron-donating and electron-withdrawing salicylaldehydes afford different selectivity in this alkenylation reactions.

    TABLE OF CONTENT Page ABSTRACT V LIST OF SCHEMES IX LIST OF TABLES X ABBREVIATIONS XI LIST OF PUBLICATIONS XIII CHAPTER 1: Rh-Catalyzed Oxidizing Group-Directed ortho C−H Vinylation of Arenes by Vinylstannanes 1 1.1 Introduction 2 1.2 Results and Discussion 9 1.3 Mechanistic Discussion 17 1.4 Applications 21 1.5 Conclusion 22 1.6 Experimental Section 22 1.7 Spectroscopic Data 30 1.8 References 44 CHAPTER 2: Cobalt-Catalyzed Oxidative Annulation of Nitrogen-Containing Arenes with Alkynes: An Atom-Economical Route to Heterocyclic Quaternary Ammonium Salts 50 2.1 Introduction 51 2.2 Results and Discussion 62 2.3 Mechanistic Experiments: 70 2.4 Applications 72 2.5 Conclusion 74 2.6 Experimental Section 74 2.7 Spectroscopic Data 81 2.8 References 101 CHAPTER 3: Rhodium(III) Catalyzed Formyl C–H Bond Activation of Salicylaldehydes with Methylenecyclopropane: An Unprecedented Selectivity between β-Hydride Elimination and Protonolysis 107 3.1 Introduction 108 3.2 Results and Discussion 118 3.3 Mechanistic Experiments: 124 3.4 Applications 127 3.5 Conclusion 128 3.6 Experimental Section 128 3.7 Spectroscopic Data 130 3.8 References 159 Crystal Structures, 1H and 13C NMR Spectra 165

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