Study On The Coupling Reaction And N-Acylimine Reduction Reaction Based On Activated Amide N-C Bond Cleavage

As a unique functional group,amide is widely distributed in proteins,drug molecules,natural products,pesticides and polymers.Its direct functional grouping has always been a core issue in organic synthesis.In recent years,the coupling reactions of various activated amides as electrophiles and nucleophiles have emerged in an endless stream,which has attracted extensive attention and become a new research hotspot in organic synthesis.The development of new amide synthons is particularly important in the functionalization of amides;at the same time,catalyst-and ligand-controlled reactions are also pursued in the field of amide research;in the absence of transition metals,the development of functionalized reactions of activated amides Enthusiasm is widely studied;at the same time,the development of a new nucleophile coupling reaction with our amide is also an important cause of amide hot spots.The nucleophilic addition reaction of imide has been one of the hotspots in organic synthesis research.The structural fragments of the corresponding products are widely present in physiologically active natural products and pharmaceutical compounds.Based on the above research background,my work is mainly divided into the following three parts:1.The first part develops a simple and efficient reaction to the direct conversion of primary amides and aryl sulfides to thioester derivatives without transition metal.The reaction synthesizes a variety of thioester compounds widely present in proteins and organisms,and successfully achieves a gram-scale experiment,which has great application value for synthesizing thioester derivatives in industrial production.2.The second part develops a transamide amidation reaction of nickel-catalyzed saccharin amide with tertiary amine.Compared to most of the reported transamidation reactions,we apply tertiary amines to the conversion of amides,and the reaction conditions are simple and mild,and can be achieved without the addition of ligands and bases.This reaction not only increases our understanding of saccharin amide activity,but also provides direction for further development of amide and tertiary amine reactions in order to further expand the nucleophile species.3.The third part develops a palladium-catalyzed hydrogenation reduction reaction of N-acylimine with water.The reaction uses water as a source of hydrogen to achieve hydrogen addition at atmospheric pressure in a system of palladium and B₂nep₂,and the reaction is safe and efficient.