Synthesis Of Triflyl-containing Compounds

The introduction of a trifluoromethanesulfonyl（triflyl,SO₂CF₃,Tf）group to the organic compound can significantly enhance the acidity,lipophilicity,and stability of the parent compound.The Tf-containing compounds have been widely used in pharmaceuticals,biology,materials and other fields.The common synthetic methods of CF₃SO₂-containing compounds include oxidization of CF₃S-containing compounds and trifluoromethylation of the sulfides.The direct triflylation methods are still limited.Therefore,the development of new triflylation methods has great significance.In the thesis,the new methods for the preparation of aryl and vinyl triflones were investigated.Part Ⅰ: The reaction of phenylsulfinate salts and TMSCF₃ for the preparation of aryl triflones was attempted.A series of reaction conditions have been investigated.However,the results are unsatisfactory and the yield of the desired product is poor.Part Ⅱ: The regioselective addition reaction of styrenes with CF₃SO₂ Na at room temperature was investigated.A number of reaction conditions including iodine source,base,metal,solvent,and equivalent were screened.This protocol provided a practical and efficient approach to vinyl triflones in high yields.Subsequently,we studied the Michael addition reaction of the resulting vinyl triflones with different C-,O-,N-,and S-nucleophiles.The vinyl triflones were proven to be excellent Michael addition acceptors to afford the addition products in good yields.