Transition-Metal-Catalyzed C7-and N-Arylation Of Indoles (Indolines) With Arylsilanes

Indole is an important organic heterocyclic compound which exists widely in nature and mainly exists in natural flower oil,and it is widely used in medicine,materials and other fields.The assembly and modification of indoles through coupling reaction is an important strategy for the diversification of indole skeleton structure.In the literature review part,We summarize the C-C coupling arylation reactions with arylsilane and Cu-catalyzed C-N coupling arylation reactions with arylsilane.In the introduction of Chapter 2 and Chapter 3,we summarized the research progress of C7-arylation and N-arylation of indole,as well as N-arylation of amine respectively.This paper aims to develop a mild and environmentally friendly aromatization reaction.We chose organosilicon reagents as the coupling reagents with the obvious advantages of easy availability,low toxicity,easy operation,high stability and environmental friendliness.The arylation reaction of indoline and indole was studied.The main work includes the following two parts:1.Rh（III）-catalyzed C7-arylation of indolines.[Cp*Rh Cl₂]₂was used as catalyst for the selective aromatization of indoline and arylsilane at C7 position by C-H activation.The reaction uses pyrimidine as the guiding group,Ag F as the fluorine source and oxidant activated by C-Si bond,and Cu SO₄as the co-oxidant can further improve the reaction yield.2.Cu-catalyzed N-arylation of indoles and arylamines.The N-arylation reaction of indole and aryl amine was developed by using aryl silicon reagent as aryl source,Cu（OAc）₂as catalyst,and tetrabutylammonium fluoride（TBAF）as fluorine source.it is worth noting that the reaction uses O₂as the oxidant and does not require the addition of additional bases and ligands.In addition,the reaction can also be applied to aryl amines,and the same good results have been obtained.