Synthesis Of Hydroxyalkylated Nitrogen-Containing Heterocycles With Visible Light

With the development of science and technology,the industrial upgrading of the society was undergoing in the direction of resource conservation and environmental friendliness.In recent years,the field of organic synthesis has also been developed,in which the research on the photocatalytic reactions have received extensive attention.Visible light photocatalysis has the characteristics of mild conditions,high efficiency,and excellent selectivities,which provides an effective way for the late modification of drug moleculers.Nitrogen-containing heterocycles are ubiquitous scaffolds in biologically active compounds,and are also versatile intermediates in the synthesis of medicines and pesticides.Hydroxyalkylated quinoline and hydroxyalkylated indolinone derivatives play an important role in human life,and industry,due to their good biological activities.Minisci reaction is an important method for the synthesis of complex nitrogen-containing heterocycles,which can directly realize the late-stage functionalization of nitrogen-containing heterocycles.Bifunctionalization of acrylamides is an efficient strategy for the synthesis of diverse indolinone derivatives.The theme of this dissertation is"Synthesis of Hydroxyalkylated Nitrogen-Containing Heterocycles with Visible Light",including:（1）photoredox neutral decarboxylative hydroxyalkylations of heteroarenes withα?keto acids.（2）visible light induced aryl-hydroxyalkylation of N-arylacrylamides with benzyl alcohols.The details are as follows.1.Visible light-induced decarboxylation hydroxyalkylation Minisci reaction,usingα-keto acid and heterocycles as raw materials,[Ir（dF（CF₃）ppy）₂（dtbbpy）]PF₆ as photocatalyst,Zn（OTf）₂ as additive,under nitrogen atmosphere.A series of hydroxyalkylated products were obtained in moderate to high yields.The reaction features the advantages of mild conditions and wide substrate scope.2.Visible light-induced aryl-hydroxyalkylation of N-arylacrylamides.This method uses benzyl alcohol and N-arylacrylamide as raw materials,[Ir（dF（CF₃）ppy）₂（dtbbpy）]PF₆ as photocatalyst,and LiBr as additive,furnishing a series of 3-hydroxyalkylindole ketone compounds.The reaction has the characteristics of simple conditions,green and sustainable visible light photocatalysis.