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Copper-mediated Aminosulfonylation Of Unsaturated Compounds-Synthesis Of Sulfone-containing Heterocyclic Compounds

Posted on:2021-02-02Degree:MasterType:Thesis
Country:ChinaCandidate:J M ChenFull Text:PDF
GTID:2381330623476353Subject:Organic Chemistry
Abstract/Summary:
Alkenes and alkynes are one of the most common and widely used starting materials in organic synthesis.With them,many important molecular skeletons can be synthesized simply and efficiently,which have promoted the rapid development of medicine and materials.Therefore,it is of great significance both academical and industrial to continue to carry out synthetic research around their transformations.In recent years,remarkable progress has been made in the construction of novel functionalized carbon ring or heterocyclic compounds by using the series cyclization/bifunctional group strategy of unsaturated compounds and another component.Among them,sulfone-containing cyclic compounds have become one of the important research directions due to their unique structure and characteristics.At present,with the efforts of chemists,a variety of transition metals,non-transition metals,and photocatalytic synthesis methods use unsaturated compounds and sulfone reagents.However,in these reactions,the conditions for the synthesis of sulfoxide containing carbon/heterocyclic compounds are still insufficient,such as harsh conditions and limited application range of substrates.Therefore,there is a need to further develop simple,efficient and environmentally friendly synthetic methods to construct sulfone-substituted carbon / heterocyclic compounds.In this context,we also explored the construction of sulfone-containing cyclic compounds,and reported a copper-catalyzed / promoted sulfonylation reaction of 2-vinylbenzamide with sodium sulfinate.In addition,in order to further elaborate the reaction mechanism,we also conducted a series of control experiments.This paper is divided into three chapters:The first chapter mainly introduces the research progress of copper catalyzed alkyne/alkyne sulfone reaction,and also briefly introduces the research progress of other transition metals,without transition metals and photocatalyzed alkyne/alkyne sulfone reaction.The second chapter,we developed copper catalyzed / promoted the aminosulfonylation of 2-vinylbenzamide with sodium sulfinate to synthesize a series of sulfoned lactams.The C-N and C-S bonds were constructed by tandem cyclization of olefin.This method uses easy-to-obtain and stable sodium sulfinate as the sulfone reagent,and also has the advantages of easy operation,mild reaction conditions,and good functional group tolerance.The third chapter,conclusions and prospects.On the basis of our existing copper-mediated sulfonylation reaction of 2-vinylbenzamide and sodium sulfinate,we will continue to study the sulfone reaction of other olefin / alkyne substrates,and we hope to further synthesize structure-rich sulfone-containing heterocyclic compounds.
Keywords/Search Tags:Alkenes, Alkynes, Sulfone Reaction, Copper Promoted/Catalyzed, Lactam Compounds
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