銠金屬催化之碳－氫鍵活化反應以合成含氮雜環衍生物及相關天然物之研究

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研究生：	賈亞庫馬 Jayakumar
論文名稱：	銠金屬催化之碳－氫鍵活化反應以合成含氮雜環衍生物及相關天然物之研究 Rhodium(III)-Catalyzed C–H Activation as a Key Step for the Synthesis of N-Heterocycles and Related Natural Products
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 鄭建鴻 Cheng, Chien-Hong 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：	2014
畢業學年度：	102
語文別：	英文
論文頁數：	248
中文關鍵詞：	銠金屬、碳氫鍵活化、異喹啉、醛、炔、胺、苯亞胺
相關次數：	點閱：2 下載：0
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Transition-metal-catalyzed C‒C bond formation reaction by uniting readily available π-components is an attractive strategy to synthesis biologically important compounds in a single operation with high atom-efficacy. Particularly, C H bond activation reactions are experienced method to synthesis of natural products and biologically important compounds in a highly regioselective manner. The C H functionalization of aryl aldehydes with amines and alkynes to afford highly substituted isoquinolines. On the other hand multiple C H activations of N-hyroxybenzamidines with alkynes afforded highly substituted hetroaromatic compounds in one-pot manner. For better understanding, I divided this thesis into four chapters. The first three chapters describe about rhodium-catalyzed inter and intramolecular C-H activation/annulation of aldehydes with amines and alkynes or (amino-alkynes). The final chapter describe about the multiple C H activations of N-hyroxybenzamidines or (aryl nitrile and amines) with alkynes using rhodium(III) as the catalyst.
 Chapter 1 describes a new method for the synthesis of isoquinolinium salts from the oxidative coupling/annulation of alkynes with aldehydes and amines via Rh(III) catalysis. The proposed mechanism is strongly supported by the isolation of a five-membered rhodacycle and an intermediate organic compound. This protocol successfully applied to the total synthesis of Oxychelerythrine with 66% overall yield.

 Chapter 2 deals with the synthesis of quaternary protoberberine alkaloids (QPA) from aldehydes and aminoalkynes with Rh(III)-salt complex. The reaction can be applied to a straight forward synthesis of 13-substituted protoberberine natural products.

 Chapter 3 illustrates a rhodium-catalyzed synthesis of N-heterocycles from aldehydes, amines and alkynes by C-H activation method. This is the first example of an imine-directed synthesis of highly substituted isoquinolones in one-pot.

 Chapter 4 is about the synthesis of polyhetreoaromatics from N-benzamidines and alkynes by multiple rhodium-catalyzed C H activation and annulation steps. A possible mechanism is proposed involving multi-step chelation-assisted ortho-C–H activation, alkyne insertion and reductive elimination

TABLE OF CONTENTS
    Page
ABSTRACT       IV
LIST OF SCHEMES      VI
LIST OF TABLES     IX
LIST OF FIGURES     X
ABBREVIATIONS    XI
LIST OF PUBLICATIONS    XIV
CHAPTER 1: One-Pot Synthesis of Isoquinolinium Salts by Rhodium Catalyzed C-H Bond Activation: Application to the Total Synthesis of Oxychelerythrine    1
1.1 Introduction    3
1.1.1 General Introduction of Transition Metal-Mediated C–H Bond Functionalization    3
1.1.2 Introduction to Isoquinoline    5
1.1.3 Transistion Metal Catalysed Synthesis of Isoquinoline    6
1.2 Objective    11
1.3 Results and Discussion    11
1.3.1 Optimization Study for Suitable Solvent and Silver Salt    11
1.3.2 Optimization Study for Suitable Oxidant    13
1.3.3 Scope of the Reaction    14
1.4 Mechanistic Discuission     19
1.4.1 Mechanistic as well as Intermediate Isolation    20
1.4.2 Reaction of Rhodacycle I with Phenyl-1-Propyne (2d) and Phenylacetylene 2f    21
1.5 Application to the Total Synthesis of Oxychelerythrine    22
1.6 Conclusion    24
1.6 Experimental Section    24
1.7 Spectroscopic Data    26
1.8 References    39
    
CHAPTER 2: Synthesis of Quaternary Protoberberine Salts involving Rh(III)-Catalyzed C-H Bond Activation as a Key Step and Annulation    42
2.1 Introduction    44
2.1.1 Introduction to Quaternary Protoberberines    44
2.1.2 Classical Methods for the Total Synthesis of 13-Methylpalmatine Natural Product    46
2.1.3 Intramolecular Alkenes Redox-neutral Cyclization Reactions        47

2.1.4 Intramolecular Alkynes through C–H Activation/Annulation Reactions    50
2.2 Objective    52
2.3 Results and Discussion    53
2.3.1 Optimization Studies    53
2.3.2 Scope of the Reaction    54
2.3.3 Results of the Aminoalkynes and α,β-Unsaturated Aldehydes    60
2.4 Mechanistic Discussion    62
2.4.1 Regioselectivity Confirmation of Product 3p    63
2.5 Gram-scale Reaction    64
2.6 Application to the Synthesis of unknown Protoberberine Alkaloids    64
2.7 Conclusion    66
2.8 Experimental Section    67
2.9 Spectroscopic Data    69
2.10 References    94
CHAPTER 3: Efficient Synthesis of Isoquinolones by Rhodium Catalyzed C-H Bond Activation    99
3.1 Introduction    100
3.1.1 Introduction to Isoquinolone or Isoquinolin-1(2H)-one (Isocarbostyril)    100
3.1.2 Synthesis of Isoquinolone by Transition Metal Catalyzed Cyclisation/Annulation    101
3.1.3 Transition Metal Catalyzed Synthesis of Isoquinolone by C-H Activation/Annulation    103

3.2 Objective    108
3.3 Results and Discussion    108
3.3.1 Optimization Study for Suitable Oxidant    108
3.3.2 Scope of the Reaction    110
3.4 Mechanistic Discussion    115
3.4.1 Mechanistic Evidence for the Synthesis of Key Intermediate     116
3.5 Conclusion    117
3.6 Experimental Section    118
3.7 Spectroscopic Data    118
3.8 References    127
CHAPTER 4: One-Pot Synthesis of Highly Substituted Polyheteroaromatics by Rh(III)-Catalyzed Multiple C–H Activation and Annulation    131
4.1 Introduction    132
4.1.1 Introduction to benzonapthyridine     132
4.1.2 Synthesis of Benzo[1,8]naphthyridine Tradional Methods    133
4.1.3 General Introduction of Transition Metal Catalyzed Multiple C-H Activation/Annulation       135
4.2 Objective    140
4.3 Results and Discussion    140
4.3.1 Optimization Studies    140
4.3.2 Scope of the Reaction    142
4.3.3 Scope of the Reaction with Aliphatic Alkynes    147
4.3.4 Scope of the Reaction with Nitriles, Amines and Alkynes    148
4.4 Mechanistic Discuission     152
4.4.1 Isolation of the Intermediates    153
4.4.2 Competition Experiments         155
4.5 UV-PL Studies for the Compounds of 3    157
4.6 Conclusion    159
4.7 Experimental Section    159
4.8 Spectroscopic Data    160
4.7 References    177
Crystal Structures, 1H and 13C NMR Spectra    183

    LIST OF SCHEMES    
    
CHAPTER 1    
    
Scheme 1.1: Retrosynthetic Disconnections of the Isoquinoline Core.    5
Scheme 1.2: Synthesis of Isoquinolines from Cyclopalldated Benzaldimines and Internal Alkynes.    7
Scheme 1.3: Jun Heterocycle Synthesis.    8
Scheme 1.4: Rhodium(III)-Mediated Isoquinoline Salt Formation by Jones.    8
Scheme 1.5: Synthesis of Isoquinoline with Rh(III)-Catalysed by Fagnou.    8
Scheme 1.6: Isoquinolines from Aryl ketone O-Acyloxime Derivatives and Internal Alkynes.    9
Scheme 1.7: Synthesis of Isoquinolines from Benzaldimines and Internal alkynes Annulation.    10
Scheme 1.8: Isoquinolines from o-Halobenzaldimines or Iminoalkynes annulation.    10
Scheme 1.9: Isoquinolines from Aryl ketone O-Acyloxime Derivatives and Internal alkynes.    10
Scheme 1.10: Retro Synthetic Route for Metal Catalysed Synthesis of Isoquinolinium Salts.    11
Scheme 1.11: Ortep Diagram of Compound 4a.    19
Scheme 1.12: Proposed Mechanistic Pathway for the formation of  Isoquinolinium salt 4q    20
Scheme 1.13: Ortep Diagram of Rhodacycle I.    21
Scheme 1.14: Reaction of Rhodacycle (I) with Alkynes.    22
Scheme 1.15: Total Synthesis of Oxychelerythrine (7).    23
Scheme 1.16: The C-H Activation of a-β-Unsaturated Aldehydes, Amines and Alkynes.    24
    
CHAPTER 2    
    
Scheme 2.1: Synthetic Methods of Protoberberine Derivatives    47
Scheme 2.2: Rh(III)-Catalyzed Enantioselective Intramolecular Hydroarylation of Alkenes via C–H Bond Activation.    48
Scheme 2.3: Rh(III)-Catalyzed Intramolecular Hydroarylation, Amidoarylation, and Heck-type Reaction.    48
Scheme 2.4: Chiral Rh(III)-Catalyzed Asymmetric Hydroarylations of 1,1- Disubstituted Alkenes.    49
Scheme 2.5: Rh(III)-Catalyzed Intramolecular Redox-neutral Cyclization of Alkenes via C–H Activation.    50
Scheme 2.6: Rhodium Catalyzed Redox-neutral Annulation of Aromatic amides with Alkynes.    50
Scheme 2.7: Rhodium(III)-Catalyzed Intramolecular Annulations involving Amide-directed C–H Activations.    50
Scheme 2.8: Synthesis of the Homoprotoberberine Framework by Glorious.    51
Scheme 2.9: Synthesis of Various Nitrogen Containing Salts by Cheng Groups.    52
Scheme 2.10: Retro Synthetic route for the Synthesis of Protobereberine Salt    53
Scheme 2.11: Proposed Mechanistic Pathway for the formation of Protoberberine Salt.    63
Scheme 2.12: Ortep Diagram of 3p.    64
Scheme 2.13: Scale-up Reaction.    64
Scheme 2.14: Ortep Diagram of 8    65
Scheme 2.15: Synthesis of Quaternary Protoberberine Alkaloids (6-10)..    66
    
CHAPTER 3    
    
Scheme 3.1: Main Strategies for the Synthesis of Isoquinolone core by Metal Catalyzed Cascade Processes    102
Scheme 3.2: Strategies for Heterocycle formation through Cross-Coupling/ Cyclization    103
Scheme 3.3: Rh(III)-Catalyzed Redox-Neutral Annulation of Aromatic-amides with Alkynes    104
Scheme 3.4: Rhodium-Catalyzed Oxidative Cycloaddition of Aromatic-amides with alkynes    104
Scheme 3.5: Ru-Catalyzed Oxidative Cycloaddition of Aromatic-amides with alkynes    105
Scheme 3.6: Pd-Catalyzed Oxidative Cycloaddition of Aromatic-amides with Alkynes    105
Scheme 3.7: Ni-Catalyzed Oxidative Cycloaddition of Aromatic-amides with Alkynes    106
Scheme 3.8: Rh-Catalyzed Double Directing group Strategy for the Synthesis of Isoquinolone    106
Scheme 3.9: Rh-Catalyzed Oxidative Cycloaddition of Aromatic-amides with Alkyne MIDA (N-methyliminodiacetic acid) boronates    107
Scheme 3.10: Organo-Catalyzed Oxidative Cycloaddition of Aromatic-amides with Alkynes    107
Scheme 3.11: Retro Synthetic Route for the Synthesis of Isoquinolone with Rh(III)-Catalyzed one-pot Reaction    108
Scheme 3.12: Proposed Mechanistic Pathway for the formation of Isoquinolone (4a)    116
Scheme 3.13: Isolation and Evidence for the Formation of Isoquinolone (4a)    117
    
CHAPTER 4    
    
Scheme 4.1: Cascade Cyclization of Nitriles to Fused, Aromatic Molecules.    134
Scheme 4.2: Classical Methods for the Synthesis of Benzo[1,8]naphthyridine Derivatives.    135
Scheme 4.3: Rh(III)-Catalyzed Multiple C-H/N-H Activation by Miura et al.    136
Scheme 4.4: Rh(III) Catalyzed Dual C-H/N-H Activation by Xingwei Li et al    137
Scheme 4.5: Rh(III) Catalyzed Multiple C-H/O-H Activation by Wang et al.    138
Scheme 4.6: Rh(III) Catalyzed Dual C-H/N-H Activation by Cheng et al    139
Scheme 4.7: Rh(III) Catalyzed Dual C-H/N-H activation by Cheng et al.    139
Scheme 4.8: Pd(II) Catalyzed Dual C-H/N-H Activation by Wang et al    140
Scheme 4.9: Retro-synthetic Route for the Synthesis of Polyhetroaromatics with Rh(III)-Catalysed one-pot Reaction.    140
Scheme 4.10: Ortep Diagram of Compound 5e.    151
Scheme 4.11: Proposed Mechanism for the formation of Benzoisoquinolinonaphthyridines Derivatives.    153
Scheme 4.12: Isolation of Intermediate 4 and its Reaction with Alkynes.    154
Scheme 4.13: Isolation of Intermediate 4b and Competitive Experiments between Nitrile and Aldehyde with Amine and Alkyne.    155
Scheme 4.14: Ortep Diagram of Compounds 4b and 8.    156
Scheme 4.15: Absorption and Fluorescence Spectra of 3.    157
Scheme 4.16: The UV-Vis Absorption and Emission Spectra of Compounds 3t and 5d in toluene.    158
    
    
LIST OF TABLES    
    
CHAPTER 1    
    
Table 1.1: Silver Salt and Solvent Optimization Studies for the Rh(III)-Catalyzed Isoquinolinium Salts from Benzaldehyde, Methyl Amine with Diphenylacetylene    12
Table 1.2: Oxidant Optimization Studies for the Rh(III)-Catalyzed Isoquinolinium Salts from Aryl Aldehyde, Methyl Amine with Alkynes    13
Table 1.3: Results of Rhodium-Catalyzed C-H Activation and Annulation of Benzaldehydes, Methyl amine and Alkynes    15

CHAPTER 2    
    
Table 2.1: Optimiztion Studies for the Rh(III)-Catalyzed formation of Protoberbernium salt 3a from 1a and Aminoalkyne 2a.    44
Table 2.2. Results of Rh-Catalyzed C–H Activation and Annulation of Benzaldehydes, with Aminoalkynes    57
Table 2.3: Results of Rhodium-Catalyzed C-H Activation and Annulation of α,β-Unsaturated Aldehydes and Amino-alkynes    63
    
CHAPTER 3    
    
Table 3.1: Oxidant Optimization Studies for the Rh(III)-Catalyzed C-H Activation    109
Table 3.2: Results of Rhodium-Catalyzed C-H Activation and Annulation of Benzaldehydes, Methyl amine and Alkynes    111
    
CHAPTER 4    
    
Table 4.1: Optimization Studies for the Rh- Catalyzed C-H Activation of N-Hydroxybenzamidines with Alkynes    141
Table 4.2: Results of the Reaction of N-Hydroxybenzamidines 1a-m with Alkynes 2a-f    143
Table 4.3: Results of the Reaction of Oximes 1b with Alkynes 2g-i    148
Table 4.4: Results of Rhodium-Catalyzed C-H Activation and Annulation of Benzonitriles, Methylamine and Alkynes    149
Table 4.5 Absorption and Fluorescence Spectra of 3i, 3j, 3l and 3r    158



LIST OF FIGURES    
    
CHAPTER 1    
    
Figure 1.1: Proposed Mechanism for C(sp2)–H bond Functionalization    4
Figure 1.2: Natural Products Containing Isoquinoline Motif    6

CHAPTER 2    
    
Figure 2.1: Protoberberine Core Alkaloids .    44
Figure 2.2. Natural products Containing Quaternary Protoberberines    46
    
CHAPTER 3    
    
Figure 3.1: Natural Products Containing Isoquinoline-1(2H)-one Core Structures    78
    
CHAPTER 4    
    
Table 4.1: Natural Products Containing Benzonapthridine Core Structures    133




                                

Chapter-1
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Chapter-2
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