Study On Acylation And Thiolation Via Transition-Metal-Catalyzed C(sp~2)-H Functionalization Assisted By Directing Groups

In recent years, transition-metal-catalyzed C-H functionalization involving directing groups has made tremendous progress. It has become one of the most powerful tools in modern organic synthetic chemistry for the selective formation of carbon-carbon and carbon-heteroatom bonds. Owing to their atom and step economy in synthetic chemistry, C-H functionalization has received much attention. This thesis mainly discloses transition-metal-catalyzed acylation and thiolation of C(sp2)-H bonds assisted by directing groups, which chiefly involves the following three parts.In chapter I, the development of transition-metal-catalyzed C-H functionalization assisted by directing groups has been summarized systematically. And transition-metal-catalyzed direct acylation and thiolation of C(sp2)-H bonds has been presented in detail.In chapter II, we described palladium-catalyzed C2-acylation of indoles with aryl and alkyl aldehydes. This method uses aromatic, aliphatic, and conjugated aldehydes as the acyl sources, showing excellent functional group tolerance, and providing a convenient and straightforward access toward various types of 2-aroylindoles.In chapter III, we summarized copper-catalyzed direct thiolation of C-H bonds in aromatic amides with aryl and aliphatic thiols. In this transformation, the substrate scope is quite broad. 8-Aminoquinoline amides can react well with 1°,2°,3° aliphatic thiols and thiophenols, and the thiolated products were obtained in moderate to good yields.