| ABSTRACT | 第4页 |
| 1 INTRODUCTION | 第7-28页 |
| Research background | 第7-8页 |
| 1.1 Research significance of indole C-H bond functionalization reaction | 第8-9页 |
| 1.2 Functionalization of indole with non-directing groups | 第9-22页 |
| 1.2.1 Non-directing group assisted alkylelation of indole | 第10-13页 |
| 1.2.2 Non-directing group assisted allylation of indole | 第13-15页 |
| 1.2.3 Non-directing group assisted arylation of indole | 第15-19页 |
| 1.2.4 Alkylation of indole without directing group | 第19-20页 |
| 1.2.5 Amination of indole assisted by without directing group | 第20-21页 |
| 1.2.6 Non directing group assisted Oxyalkylation of indole | 第21-22页 |
| 1.2.7 Non directing group assisted halogenation of indole | 第22页 |
| 1.3 Progress in functionalization of indole with directing groups | 第22-28页 |
| 1.3.1 Directing group assisted alkylation of indole | 第22-23页 |
| 1.3.2 Directing group assisted methylation of indole | 第23-25页 |
| 1.3.3 Indole chlorination reaction assisted by directing group | 第25页 |
| 1.3.4 Directing group assisted cyanation of indole | 第25-26页 |
| 1.3.5 Directing group assisted indole Methylthiolation reaction | 第26-28页 |
| 2 LITERATURE REVIEW | 第28-39页 |
| Transition metal catalyzed C(SP2)-H Alkynylation | 第28-30页 |
| 2.1 Progress in the alkynylation of indole | 第30-39页 |
| 2.1.1 Alkynylation of indole without directing group | 第32-36页 |
| 2.1.2 Directing group assisted alkynylation of indole | 第36-39页 |
| 3 RESULTS AND DISCUSSIONS | 第39-68页 |
| 3.1 Study on the Alkynylation of C2-based indoles catalyzed byPalladium | 第39-42页 |
| 3.2 Optimization of experimental conditions | 第42-43页 |
| 3.3 Optimization of catalyst | 第43页 |
| 3.4 Optimization of base | 第43-45页 |
| 3.5 Optimization of reaction conditions | 第45-47页 |
| 3.6 Scope of C-2 alkynylation of indoles | 第47-48页 |
| 3.7 Application of indoles C2-based alkynylated products | 第48-49页 |
| 3.8 Reaction mechanism speculates | 第49页 |
| 3.9 Synthesis and characterization of substrates | 第49-53页 |
| 3.10 Alkynylation of 3-methyl-2-phenylpyridine | 第53-55页 |
| 3.11 NMR results of experiments | 第55-68页 |
| 4 CONCLUSION | 第68-69页 |
| ACKNOWLEDGEMENTS | 第69-70页 |
| REFERENCES | 第70-75页 |
