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Synthesis Of 1,5-Diene Compounds Enabled By Photoredox/Palladium Cocatalysis

Posted on:2022-08-27Degree:MasterType:Thesis
Country:ChinaCandidate:M H TangFull Text:PDF
GTID:2491306725991079Subject:Chemistry
Abstract/Summary:
As one of the most important organic compounds,olefins are widely present in organic materials,biologically active molecules,and pesticides.1,5-Diene compounds occupy an important position in the huge olefin family with their unique chemical properties.It not only exists in many active molecules,but also an important synthetic building block in organic synthesis.Chemists have conducted a lot of research on the synthesis method of 1,5-diene compounds.Its synthesis difficulty lies mainly in the control of chemoselectivity.At present,the main synthesis methods of 1,5-diene compounds can be divided into two categories: transition metal catalysis and non-transition metal catalysis.In recent decades,with the continuous efforts of the majority of chemists,the development of various transition metal catalysis models has become more and more mature.Transition metal catalysis occupies an important position in modern organic synthesis due to its high reaction activity and high reaction selectivity.In recent years,photochemistry has attracted the interest of a large number of chemists.This new type of catalytic mode can produce highly reactive free radical intermediates under mild reaction conditions,which can achieve the transformations that cannot be achieved in traditional reactions.In this catalytic mode,controlling the selectivity of the reaction is the main difficulty.In order to solve the problem of selectivity,chemists creatively combined photochemistry and transition metal catalysis modes,providing a new idea of synergistic catalysis between transition metals and light.In this paper,the synthesis of 1,5-diene compounds by palladium and photocatalysis is the main research content.This paper focuses on the following two parts:The first part,through the palladium and photo-cooperative catalytic mode,the reductive self-coupling of allyl acetate is realized,thereby realizing the construction of polysubstituted(Z,Z)-1,5-diene compounds.The second part,based on the mode of palladium and photo-co-catalysis,a racemic 1,5-diene compounds containing a chiral quaternary carbon center was constructed,and a preliminary attempt was made to construct a chiral 1,5-diene compounds.
Keywords/Search Tags:Palladium and Light Synergistic Catalysis, 1,5-Diene Compounds, Light-induced Double Bond Isomerization, Chiral Quaternary Carbon Center
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