| Over the past decade, C-H functionalization has received great attention by many chemical researchers. The traditional coupling methods can not meet the demand for the synthesis of huge compounds system. Therefore, C-H functionalization undergo an explosive development naturally. Generally, high site selective C-H transformation needs a directing center to realize the effective C-H functionalization. Thus the directing group strategy is one of the most important strategies in furnishing this goal. In this thesis, a new calss of N,O-bidentate directing group for amine and carboxylic acid is well expored. Herein a general method to realize the etherification, acetoxylation, and alkynylation for amines and carboxylic acid is developed.The whole thesis is mainly composed of following three parts.In part one; various types of bidentate directing groups are classed. Then, the etherification, acetoxylation and alkynylation via C-H functionalization are also well reviewed.In part two; palladium-catalyzed oxamide directed γ-C-H etherification and acetoxylation for amine substrates is described. The inactive C(sp3)-H can also realize the acetoxylation by modifying the reaction conditions. A possible reaction mechanism is also proposed. The newly developed protocol provides a new approach for C-O bond constructiong.In part three, palladium-catalyzed C-H alkynylation of carboxylic acid substrates via glycinamide is well developed. Various functional groups are tolerated. The protocol gives moderated to excellent yield of the ortho-alkynylated carboxylic amides products.All the products are identified by 1H NMR, 13 C NMR, partially 19 F NMR and HRMS. |
