Studies On Copper(Ⅱ)-Catalyzed C-H Functionalization

The C-H bond has low activation because of the high C-H bond energy (such as the C-H bond energy of methane is up to 439 kJ/mol) and low polarity, therefore, to gain series of products via C-H functionalization has always been the dream of organic chemists for a long time. The C-H activation shown the important theoretical value in organometallic chemistry. The functionalization of C-H bond via transition metal catalysis, especially using the directing groups, has become the hot topic in the organic chemistry. This dissertation consists of three parts:The first part:the reviews on the development of C-H activation catalyzed by metal Cu which is lowly toxic and cheap.The second part: we discussed the copper (II)-catalyzed acyloxylation of the sp2 C-H bond with anhydrides. Formation of C-O bond via C-H activation in the presence of copper was described by using 2-arylpyridines and anhydrides as the substrates and O2 as terminal oxidant. Moreover, we investigated the preliminary mechanism.The third part:we discussed the copper (Ⅱ)-catalyzed acyloxylation and chlorination of the sp2 C-H bond with acyl chlorides. The selectivity can be controlled via changing reaction conditions by using 2-arylpyridines and acyl chlorides as reagents. Above all, the mechanism was reasoned and verified.