銠金屬催化碳－氫鍵活化氧化反應於合成含氮雜環化合物與相關具生物活性分子的應用

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研究生：	尼堤 Upadhyay, Nitinkumar Satyadev
論文名稱：	銠金屬催化碳－氫鍵活化氧化反應於合成含氮雜環化合物與相關具生物活性分子的應用 Rhodium (III)–Catalyzed Aerobic Oxidative C‒H Activation towards N-Heterocycles and relevant Bioactive Molecules
指導教授：	鄭建鴻 Cheng, Chien-Hong
口試委員:	劉瑞雄 Liu, Rai-Shung 韓建中 Han, Chien-Chung 莊士卿 Chuang, Shih-Ching 謝仁傑 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：	247
中文關鍵詞：	銠金屬催化反應、需氧氧化反應、水相反應、碳-氫鍵活化、環化反應、烯化反應
外文關鍵詞：	Rhodium-catalyzed reaction, Aerobic Oxidation, Aqueous medium, C-H activation, Annulation reaction, Olefination
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近年來，過渡金屬催化碳－氫鍵活化反應逐漸受到重視，因此類型反應具有高位向選擇性、不須使用官能基化之反應物、高原子經濟性且可應用於合成具生物活性之有機分子，使碳－氫鍵活化反應成為熱門的研究領域之一。於此論文中主要探討銠金屬催化於有氧環境中的分子間與分子內碳－氫鍵官能基化反應，以下分成三個章節以詳細敘述之：

第一章探討銠金屬催化2-芳基吡啶與烯化合物於氧氣下，使用純水作為溶劑，合成異吲哚啉鹽化合物。此反應中銠金屬會進行鄰位碳－氫鍵活化烯化反應，並經由氮雜－麥可加成反應、烯上β－碳去氫化與二次麥可加成，生成產物異吲哚啉鹽衍生物。

第二章敘述銠金屬催化苯甲醛與炔胺化合物進行碳－氫鍵活化與環化反應，合成異吲哚啉鹽、喹嗪鹽與吡啶并氮雜卓鹽衍生物。此合成方法成功應用於合成天然物Ficuseptine。

最後一章則講述銠金屬催化N-烷基苯甲醯胺與炔化合物於水相中與氧氣下合成高選擇性之異喹啉酮化合物。此反應可應用於較環保的合成具生物活性之含異喹啉酮骨架衍生物

In recent year transition-metal-catalyzed C‒H activation reaction got considerable attention because of catalytic reaction does not require pre-functionalization also desired product is highly regioselective and utility of reaction can be applicable to synthesis biologically important compounds in one pot operation with high atom-efficacy. In this thesis, aerobic rhodium–catalyzed inter and intra molecular C‒H Bond functionalization reactions are described. For better understanding, I divided this thesis into three chapters. The first chapter describe about rhodium-catalyzed ortho olefination via intramolecular aza-michael addition in water and oxygen as a sole oxidant. In chapter second rhodium catalyzed intramolecular C‒H activation/annulation of aldehydes with alkyne-amines demonstrated in presence of oxygen as an oxidant. The third chapter describe about synthesis of isoquinolones from N-alkyl benzamides and alkynes using Rh(III) catalyst and inexpensive oxygen as the sole oxidant in aqueous medium.

Chapter 1 describes a new method for the synthesis of Isoindolium Salts from from 2-arylpyridines and alkenes in aqueous medium under oxygen via Rh(III) catalysis. A reaction mechanism involving an ortho CH olefination of 2-arylpyridine by alkene, intramolecular aza-michael addition, deprotonation at the -carbon of the alkene fragment followed by another michael addition to give the final product is proposed.

Chapter 2 deals with the synthesis of indolizidinium, quinolizinium and pyrido[1,2-a]azepinium salts synthesized from benzaldehydes (or ,-unsaturated aldehydes) and alkyne-amines catalyzed by rhodium complex via C–H activation is demonstrated. The present method is successfully applied to the synthesis of natural product, ficuseptine.

Chapter 3 illustrates a new approach for highly regioselective synthesis of isoquinolones from N-alkyl benzamides and alkynes using Rh(III) catalyst and inexpensive oxygen as the sole oxidant in aqueous medium, in addition the methodology can be applied to the preparation of biologically active compounds having the isoquinolone core.

TABLE OF CONTENTS
Page
ABSTRACT                V
LIST OF SCHEMES      IX
LIST OF TABLES             XIII
LIST OF FIGURES     XIV
ABBREVIATIONS            XV
LIST OF PUBLICATIONS    XVIII

CHAPTER 1: Rh-Catalyzed Regioselective Synthesis of Isoindolium Salts from 2-Arylpyridines and Alkenes in Aqueous Medium under Oxygen           1

1 Introduction            3
2 Results and Discussion    9
2.1 Optimization Studies     9
2.2 Scope of the Reaction    11
3 Mechanistic Studies            16
4 Proposed Catalytic cycle    20
5 Conclusion                    21
6 Experimental Section    22
7 Spectroscopic Data            28
8 References                    46

CHAPTER 2: Facile One-Pot Synthesis of 2,3-Dihydro-1H-indolizinium Derivatives by Rhodium(III)-Catalyzed Intramolecular Oxidative Annulation via C–H Activation: Application to Ficuseptine Synthesis          50

1 Introduction                                              52
2 Results and Discussion                                      62
2.1 Optimization Studies                                       62
2.2 Scope of the Reaction                                      64
3 Mechanistic Discussion                                      69
4 Inter- and intra-molecular Rh-catalyzed annulation reaction.  70
5 Application to the Synthesis of Ficuseptine                      72
6 Conclusion                                                      73
7 Experimental Section                                      74
8 Spectroscopic Data                                              77
9 References                                                      93

CHAPTER 3: Synthesis of Isoquinolones via Rh-Catalyzed CH/NH Activation of Substituted Benzamides Using Air as the Sole Oxidant in Water.                                                            97

1 Introduction                                              99
2 Results and Discussion                                      107
2.1 Optimization Studies                                       107
2.2 Scope of the Reaction                                      109
3 Intermolecular Competition Experiment                      113
4 Mechanistic Studies                                              118
5 Proposed Catalytic Cycle                                      120
6 Application Towards Treatment of Cardiac Atrial Fibrillation  121
7 Gram-Scale Reaction                                              122
8 Evaluation of Green metrics of the process                      122
9 Conclusion                                                      125
10 Experimental Section                                      125
11 Spectroscopic Data                                              132
12 References                                                      148
Crystal Structures, 1H and 13C NMR Spectra                      152


                                

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