Study On Difunctionalization Of Olefins With Silicon Or Sulfur-containing Compounds

The difunctionalization reaction of alkenes have an important position in organic synthesis because this transformation can introduce two different functional groups to alkenes at the same time with high selectivity.As a result,it is widely favored by chemists because of its convenience,high efficiency,economy,and strong applicability.In addition,the difunctionalization reaction of olefins is of great significance in the synthesis of some natural drugs and drug intermediates as well as the modification of drugs.Heteroatom-containing compounds skeleton structures are widely found in some natural products,pharmaceutical molecules,and some organic compound intermediates.At present,the methods of introducing heteroatomic compound structures to organic molecular skeletons have made some achievements in medicine,biochemistry,and chemical synthesis.Recently,the difunctionalization reaction of alkenes with heteroatom-containing compounds has attracted extensive research by scientists.There are many types of heteroatom compounds,and some heteroatom-containing compounds are important organic compounds in production and our life.Therefore,it is necessary to research and develop a simple and easy-to-operate method for introducing heteroatoms into the molecular structure of related compounds through the difunctionalization reaction of olefins.This thesis mainly describes the difunctionalization reaction of alkenes with heteroatom compounds initiated by peroxides to construct compounds heteroatom-containing molecules.This thesis mainly includes the following contents:In the chapter 1,the recently advance of difunctionalization of heteroatom compounds and olefins initiated by peroxides was described.It mainly includes three aspects:(i)Difunctionalization of olefins with silane compounds;(ii)Difunctionalization of olefins with thiophenol compounds;(iii)Difunctionalization of olefins with aminos.In the chapter 2,copper-catalyzed silylation of alkenes with silyl compounds and1,3-dicarbonyl compounds was realized.The reaction uses simple olefins,common silanes and 1,3-dicarbonyl compounds as substrates,peroxides as free radical initiators and Ph CF₃ as solvents.A verity of complex silicon-based compounds was constructed effectively under the conditions.At the same time,the reaction mechanism of this reaction was also explored accordingly.In the chapter 3,A cheap transition metal copper catalyst was used to realize the thioesterification reaction of olefins with thiophenol compounds or dithiol compounds and peroxides.In this transformation,alkenes reacted with various arylthiophenol compounds and peroxides and gave the corresponding functionalized ester derivatives.In this reaction,peroxide not only acts as a free radical initiator,but also as a source of ester groups.