Copper Reagent-mediated Trifluoroethoxylation Of Aryl Bromides And Heteroaryl Bromides

Fluorine atom has many features,such as high electronegativity,low polarizability,small atomic radius.Therefore,the organic chemicals which contain the atom of fluorine have a great many of advantages that others have not,which make them have wide application in pharmaceuticals,pesticide,material,construction and other industries.Over the last few years,numerous synthetic examples of the selective incorporation of fluorine-containing groups into organic molecules have been developed.Among them,trifluoroethyl aryl ethers have attracted much attention because of the high metabolic stability and significant lipophilicity of the CF3CH2O group.As a consequence of their various beneficial pharmacological activities,trifluoroethyl aryl ethers are widely used by the pharmaceutical industry in many drugs and drug candidates.However,the current synthetic methods of Ar-OCH2CF3 all depend on harsh reaction conditions,such as the use of excess copper salts,high reaction temperatures,and long reaction times.The range of substrates is extremely narrow.Transition-metal when is applied in reaction can provide environmental,economical ways.How efficiently,environmentally,economically to construct the structure of the chemical which contains the bond of Ar-OCH2CF3 has become a popular research.The text includes:construct the structure of one coordination-compound:[(phen)2Cu][OCH2CF3],which can be utilized to catalyze the heteroaryl bromides to form the chemical bond of C-OCH2CF3.Firstly,low-cost CF3CH2OH,CuCl,NaOt-Bu and 1,10-phenanthroline are used as raw materials.The solution of NaOt-Bu in THF was added to a suspension of CuCl in THF,we can get CuOt-Bu in room temperature.The resulting light yellow mixture was filtered through a layer of celite.1,10-phenanthroline in THF was added and CF3CH2OH was added dropwise in it.We can get the coordination-compound:[(phen)2Cu][OCH2CF3],which was identified by X-ray,NMR-spectroscopy and elemental analysis.Secondly,the reagent can react with aryl and heteroaryl bromides,which lead to the synthesis of the chemical bond of C-OCH2CF3.The products can be separated and purified easily.Finally,similar coordination-compounds:[(phen)2Cu][OCH2CF2CF3],[(phen)2Cu][OCH2CF2CF2H]were also be constructed in same ways,which can also react with heteroaryl bromides.