Asymmetric Addition Reaction Of Amidodifluorophenes

Fluorinated compounds appear in all aspects of life,especially chiral fluoride widely exists in drug molecules,and plays a vital role in the treatment and diagnosis of human diseases.Traditional synthesis methods of fluorine-containing compounds directly convert relevant common functional groups into C-F through electrophilic,nucleophilic,and free radical reactions.Now the synthesis of fluorine-containing compounds is more inclined to generate new fluorine-containing compounds from known fluorine-containing compounds.Amidodifluorophene is a kind of easily obtained fluorine-containing compound with multiple reaction sites,but there are relatively few studies on the new reaction of amidodifluorophene.In this paper,starting from the compound of amidodifluorophene,under the catalysis of copper,attempts to react at different reaction sites of amidodifluorophene under different conditions,and more complex and diverse fluorine compounds were synthesized efficiently.At the same time,we also try to try the asymmetric catalysis of this kind of reaction through the screening of chiral ligands and other reaction conditions,in order to obtain chiral fluorinated compounds.The main contents of this paper are as follows:1.Under mild reaction conditions,amantadine of α-fluoro-2-pyridinyl acetate reacts with α-site of amidodifluorophene under copper catalyst to obtain continuous chiral fluorocarbon containing compounds with high yield,high dr Value and high ee value.The product has adjacent chiral centers,one of which is a tertiary carbon center containing fluorine,and the other is a quaternary carbon center with difluoroenyl terminal.2.Alkyl boron reagent was prepared from easily available olefin and 9-BBN;In the presence of catalyst copper,the defluorinated alkylation of difluorophene with alkyl boron reagents resulted in the formation of monofluorophene compounds with potential axial chirality.The reaction yield is high and the substrate functional group compatibility is goo...