Study On Copper-Catalyzed Asymmetric Hydroamination Of Polyfluoroalkyl Substituted α,β–Unsaturated Alkenes

Organofluorine compounds are widely distributed in various natural products,drug molecules and materials with excellent properties,and have attracted great attention.Trifluoromethyl and difluoromethyl are one of the most important functional groups of drug and pesticide molecules.The introduction of trifluoromethyl and difluoromethyl functional groups will significantly change the physical,chemical and biological properties of organic molecules,such as permeability,lipophilicity and metabolic stability,so they are synthesized into fluorinated compounds,In particular,organic molecules containing trifluoromethyl and difluoromethyl have become one of the important research topics in organic fluorine chemistry.In addition,amines are ubiquitous in bioactive organic molecules and drug molecules,and the construction of carbon nitrogen bond is one of the most commonly used reactions in drug synthesis.Therefore,it is of great significance to construct chiral amines in organic fluorine compounds economicallyFluoroamines have important applications in biology and medicine,such as α–Trifluoromethylamine compounds β– Trifluoromethylamine compounds,long-chain trifluoromethylamine compounds and long-chain difluoromethylamine compounds.It can affect the hydrophobicity,metabolic stability and permeability of biomolecules.It also has important applications in drug development,such as drug research in the treatment of osteoporosis,hyperthyroidism and Alzheimer’s disease.In addition,chiral fluoroamines have important applications in medicine,industry and agriculture.Fluoroamines with different configurations have unique and important properties in biological properties and functional materials.For example,most of the fluoroamines in pharmaceutical chemistry are chiral.However,regioselective and enantioselective synthesis is still facing great challenges.Asymmetric synthesis of fluorinated amines has always been a hot topic in the field of synthesis.In this paper,we choose the low active fluoroalkyl group α,β– Unsaturated olefins were used as substrates.Under the catalysis of cheap copper catalyst,a series of fluorinated alkyl compounds with high enantioselectivity and regioselectivity have been achieved economically α,β– Asymmetric hydroamination of unsaturated hydrocarbons with hydroxylamine compounds.A series of chiral polyfluoroalkylamines were obtained.The conversion conditions were mild,with good functional group compatibility and high enantioselectivity(up to 99% ee).It provides a simple and efficient method for the synthesis of important fluoroalkyl amines.