Visible-light Promoted Selective TEMPO Oxidation Of Primary Alcohol&Quinazoline Synthesis Via Benzylamine Oxidation

This thesis composes with three parts as follows:In the first part, we summaried applications of visible light in organic synthesis, the addition of TEMPO to1,3-dicarbonyl compounds, oxidation of primary alcohols and synthesis of quinazoline.Second part is about our investigation of visible light promoted TEMPO selective oxidation of primary alcohol. We discovered TEMPO was oxidized to TEMPO cation under visible light and photoredox sensitizer. We utilized this discovery and successfully achieved selective primary alcohol oxidation.Next we investigated the synthesis of quinazoline through photoredox oxidation of benzylamine to imine. A new protocol of quinazoline synthesis from o-aminobenzylamine and benzaldhyde was designed and achieved successfully.In summary, through our discovery of oxidation TEMPO to TEMPO cation under visible light and sensitizer, we found that it could be applied to the selective oxidation of primary alcohols. We extended this method to the oxidation of benzylamine. We found that the oxidation of benzylamine didn’t need TEMPO. The methods have many advantages, for example, environmentally friendly, low catalyst loading, high yield, simple operation, mild conditions, easily accessible substrates, good functional group tolerance, and so on. In conclusion, it compliments to the development of research of practical and green chemistry.