Visible Light-induced Deoxygenative Reduction And Coupling Reaction

As time goes by,human society continues to develop and advance,and science and technology continue to update and progress.However,traditional non-renewable fossil resources such as coal,oil and natural gas are facing severe problems such as depletion and global environmental pollution and climate change.Chemists have focused their attention on renewable visible light,hoping to use visible light catalysis to develop mild and highly selective synthetic strategies as a new target and field of organic synthetic chemistry.Both quinoline and pyridine compounds are important nitrogen-containing heterocyclic compounds.Whether they come from nature or synthetic molecules,as pivotal fine organic synthesis frameworks,they are widely used in the fields of drugs,dyes,functional materials and daily chemicals.Seeking and developing efficient direct functionalization of nitrogen-containing heterocyclic compounds is a long-term focus of synthetic chemists.With the successive development and application of metal and organic photocatalysts,the problem that most organic molecules can’t directly absorb visible light has been solved.Mild and environmentally friendly visible light organic synthetic chemistry has attracted great attention from researchers.Therefore,how to efficiently and rapidly construct compounds containing quinoline and pyridine structures with the help of photocatalytic synthesis tools has important research significance in organic chemistry.This thesis takes"Visible Light Induced Deoxygenative Reduction and Coupling Reaction"as the theme,mainly focus on the photocatalytic deoxygenation reduction and coupling reaction using2-benzoylquinoline and sodium arylsulfinate as raw materials.The specific research content is devided into the following two parts:1.A mild visible-light-induced deoxygenative reduction of N-heteroaryl ketone/alcohol deoxygenation reaction has been developed to realize a photochemical deoxygenation reduction reaction strategy.This method use acylquinoline compounds as raw materials,4Cz IPN is used as photocatalyst,a combination of trifluoromethanesulfonic acid and（Ph O）₂PO₂H,Li Br as additive and benzaldehyde as reducing agent to obtain a series of benzyl and alkyl N-heteroaromatics.A novel formal disproportionation reaction between two carbonyls was revealed,which may inspire other designs for reductive reactions with aldehydes as reducing agent.2.A visible light-induced/Ni catalyst-mediated direct C-S bond coupling reaction of sodium sulfinate deoxidation reduction was developed at room temperature to realize the debromo-thioetherification of aryl bromides.This method mainly uses cheap and readily available（hetero）aryl bromides and stable,non-toxic and easy-to-operate sulfinates as raw materials.Many（hetero）aryl sulfide compounds were accessed with good functional group tolerance under visible light/nickel synergistic catalysis.The method is efficient and sustainable without additional base and reductant and realizes thioetherification with high selectivity.