Palladium Catalyzed Carboxylated-Directed Arylation And Alkylation Of Carboxylic Acids

The development of C-H bond activation has been one of the most popular research directions in organic chemistry in the past ten years.It can effectively shorten the reaction step in C-C bond formation via transition metal catalyzed C-H bond activation,which has the advantages of high efficiency and atomic economy.Therefore,it is the focus and hot spot for scientists to apply the strategy of C-H bond activation to the synthesis of natural products and pharmaceutical molecules.Carboxylic acids are highly important synthesis unit,being commonly found in natural products,approved drugs,and biologically important molecules.It is very direct and efficient to realize the functionalization of carboxylic acids by means of C-H bond activation compared the traditional synthesis path.The thesis maily focused on the C-C bond formation reaction of carboxylic acids by C(sp3)-H?C(sp2)-H arylaion and alkylation The main contents are as follows:First,the C-C bonding of carboxylic acids catalyzed by transition metals has been summarized.This paper mainly describes the C-C bonding reactions of C(sp3)-H and C(sp2)-H,and summarizes the characteristics,advantages and disadvantages and research significance of such reactions.Second,we systematically studied the activation of carboxylic acids and amino acids,and developed a carboxylate-directed ligand-enabled ?-C(sp3)-H arylation of aliphatic acids.The synthesis of phenylalanine and phenylpropionic acid was successfully achieved by this strategy.Finally,We found a new alkylation reagent —— aziridine.With this reagent in hand,we can complete the alkylation of benzoic acid in mild condition.This new method help to realize the introduction of ethylamine to the ortho of benzoic acid.What's more,it provides a novel route for the synthesis of phenylethylamine.