Synthesis And Application Of Halogenated Trifluoromethylated Alkenes

The introduction of trifluoromethyl groups with strong electron-withdrawing and hydrophobic property can significantly improve the bioavailability,lipophilicity and metabolic stability binding selectivity,which are widely used in many fields.Trifluoromethylation reaction of alkenes is one of the most efficient methods to introduce trifluoromethyl groups.A free-radical halotrifluoromethylation of alkenes by using Mn(OAc)3·2H2O,Na SO2CF3 and perhalogenated carboxylic acids has been achieved.Mn(OAc)3·2H2O as single electron oxidant,Perhalogenated carboxylic acids as halogen source and Na SO2CF3 as trifluoromethyl source realize halotrifluoromethylated reaction of unactivated alkenes through free radical mechanism.The reaction proceeded readily under mild conditions with good tolerance of a variety of functional groups in the substrates.The radical clock experiment and TEMPO inhibition experiment support a radical process.The halogen reagent competition experiment shows that the last step of halogenation process is mainly through halogen abstraction mechanism.The reaction has good tolerance of functional groups,mild conditions,easy operation,and can be used in kilogram-level reaction,which has great industrialization potential.The industrial design is in progress.