The Construction Of Fluorinated/Trifluoromethylated Quaternary Carbon Centers Through C-C Bond Formation Under Neutral Conditions

This dissertation is focused on the Michael reaction to construct fluorinated/trifluoromethylated quaternary carbon centers. We start our work with simple fluorinated compounds and construct mutil-functional fluorinated/trifluoromethylated molecules successfully. We also study the method to avoid β-defluorination and the mechanism of the reactions. The content mainly consist of the following two parts:Part1:The Michael addition reaction of methyl1,1-(bistrifluoromethyl) acetate with electron deficient olefins using organophosphine as a catalyst. We constructed trifluoromethylated quaternary carbon centers under mild conditions successfully, affording various desired products in excellent yields. This method reflects the important role of the control of C-F bond breakage in organic synthesis.Part2:The Michael addition reactions of α-fluoronitroalkanes with various α, β-unsaturated carbonyl compounds were realized by catalysis of low valence ruthenium species through a Csp3-H functionalization, providing a useful way to construct a fluorinated quaternary carbon center. The reactions were carried out under neutral conditions, affording desired products in moderate to excellent yields.