Oxidation And Silicalation Of Terminal Olefins And Preparation Of 2-vinylquinoline

Silicon is one of the most stocked elements on the earth.Organosilicon compounds are widely used in various materials,drugs and organisms due to their unique physical,chemical and biological activities.In recent years,the use of terminal olefin silicalation reactions to effectively construct C-Si bonds has become a hot topic in organic chemistry research.In addition,2-vinylquinoline is a compound with special research significance.It is widely used in organic synthesis and medicinal chemistry,and contains great scientific and commercial value the efficient synthesis of 2-vinylquinoline is also one of the hot topics in organic chemistry research.This thesis first systematically described the research progress in the field of C-H silicalation and free radical silicalation under the catalysis of transition metals in recent years,and based on this,designed and explored the cobalt-catalyzed silicalation reaction of olefins to synthesizeα-silyl ketone derivatives,as well as the 2-methylquinolinylation reaction involving silane.The main contents of the paper are as follows:The first chapter.This chapter focuses on the method of constructing C-Si bond.The progress of transition metal catalyzed silicalation of C-H bond and free radical silicalation were systematically described.In addition,the protection and deprotection reactions of organosilicon protecting groups and its application as reducing agent in the field of organic synthesis are briefly introduced.The second chapter.Cobalt-catalyzed oxidation and silicalation of olefins to synthesizeα-silyl ketone derivatives was developed.Theα-silicone ketone derivative was successfully synthesized by the reaction of aryl vinyl and silane in the presence of used Co（acac）₃as a catalyst and tert-butyl hydroperoxide（TBHP）as a oxidant.The structure of the product was confirmed by ¹H NMR,¹³C NMR and HRMS.The method has the characteristics of simple operation,mild reaction conditions.In addition,the gram-level response shows that the method has a potential practical value.In addition,the silicalation tandem cyclization reaction of1,6-enyne was initially explored.Experimental studies have shown that the reaction may generate a mixture of two isomers,and the mixture cannot be separated due to the similar polarities.We conducted an in-depth and comprehensive analysis of the reasons for the failure of the experiment,found the possible reason for the failure of the experiment,and ruled out a response path for the follow-up researchers.The third chapter.This chapter describes a 2-methylquinolinylation reaction promoted by silane.2-vinylquinoline was synthesized by the reaction of2-methylquinoline with DMF under the action of potassium hydroxide and triethylsilane.The structure of the product was confirmed by ¹H NMR,¹³C NMR and HRMS.This method overcomes the disadvantages of traditional synthesis methods,such as the need for transition metal catalysis,harsh and complex reaction conditions.Under the joint action of potassium hydroxide and triethylsilane,N,N-dimethylformamide can be used as an alkenylation reagent to achieve the synthesis of 2-vinylquinoline derivatives.