Transition Metal-Catalyzed Perfluoroalkylation Reaction

The inclusion of fluorinated functional groups in small molecules has had a profound impact on the pharmaceutical,material,and agrochemical industries.In particular,the Perfluoroalkyl substituent has emerged as an important functional group for the modulation of the physical properties in new pharmaceutical candidates as it has excellent metabolic stability and lipophilicity,and is electron-withdrawing in nature.As a result,much attention has been paid to the development of new synthetic methods for the introduction of perfluoroalkyl group into diverse organic compounds.However,the current method of synthesizing perfluoroalkyl compounds still has some limitations.In this paper,An efficient perfluoroalkylation of cheap starting materials and catalysts was developed.Thesis is divided into two chapters:Part Ⅰ:Synthesis of sp~2 Carbon Perfluoroalkylated Compounds by Transition Metal CatalyzedCu-catalyzed perfluoroalkylation of aryl boronic acids was developed.The aromatic perfluoroalkylation catalyzed by a copper(1)salt with perfluoroalkylzinc reagents and boronic acids,was accomplished to provide a series of the perfluoroalky lated compounds in good-to-excellent yields.The advantages of this reliable and practical catalytic reaction are 1)tolerates a wide range of functional groups 2)cheap catalyst 3)mild conditions.In addition,the mechanisms of transition-metal-catalyzed perfluoroalkylation are discussed preliminarly.Part 2:Synthesis of sp~3 Carbon Perfluoroalkylated Compounds by Transition Metal CatalyzedA general and efficient method for copper-catalyzed cross-coupling of allyl phosphates with stable perfluoroalkylznic reagents has been developed.The reaction proceeds under mild reaction conditions with high efficiency,good functional group tolerance,high region-and stereoselectivities,and provides a general,straightforward and useful access to allyl-perfluoroalkyl compounds which are of interest in life and material sciences.