Synthesis Of N-alkylated Amides And N-alkylsulfonamides

Amines are very important structural units in many natural products and other biologically active compounds. And they also exhibit a broad range of pharmacological and physiological activities.The traditional method for the synthesis of alkylated amine compounds involves the reaction of halohydrocarbon with N-alkylated amines. However, These procedures suffer from the generation of at least stoichiometric amounts of harmful waste by-products, which will cause serious environmental pollution. Recently, researchers choose alcohol instead of hydrocarbon as a as a reaction material, the amine N-alkylation reaction has many advantages: relatively mild reaction conditions, high atom economy, easy to hold the substrate, etc. This ways also will become the focus of research. Most of these catalytic systems are based on the transition metal catalysts.In the second chapter, we have demonstrated the first example for direct synthesis of N-alkylated amides from aldoximes and alcohols via tandem rearrangement/N-alkylation reaction using Ru/Ir dual catalyst system. Notably, this reaction exhibited the advantages such as easily available starting materials, excellent selectivities for N-alkylated amides, high atom efficiency and environmental friendliness.In the third chapter, the N-alkylation of P-methylbenzenesulfonamide with benzyl alcohol in water was selected as a model in water to explore the feasibility of reaction.We researched the N-alkylation of sulfonamides with alcohols in water catalyzed by water-soluble [Cp*Ir(6,6’-(OH)2bpy)(H2O)][OTf]2. From the standpoint of sustainable chemistry, the development of organic synthesis in water has becoming increasingly important because water is cheap, safe and environmentally benign. The reaction meets the requirement of green chemisty and has broad prospects for development.This research on tandem synthesis of N-alkylated amides and N-alkylsulfonamides will open up new fields for "hydrogen auto-transfer reaction" and facilitate the progress of green chemistry-directed reaction in organic synthesis.