Α- Aryl Thioamide Compound Pd- Catalyzed Glycosylation Reaction

Thioamides are unique and significant synthetic building blocks with sulfur,nitrogen, and α-carbon three adjacent nucleophilic centers, which are widely used inthe synthesis of many important molecules, as well as building a variety ofheterocyclic compounds. However, they are rarely used as carbon nucleophiles fortransition-metal-catalyzed C-C coupling reactions. This master thesis focused on thePd-catalyzed α-arylation of thioamides, providing the corresponding α-arylatedthioamides in moderate to good yields under mild reaction conditions. The currentwork includes the following three parts:1. A series of thioamide compounds were prepared by the reaction of amidesand Lawesson reagent at reflux in THF.2. Optimal reaction conditions were obtained for the Pd-catalyzed α-arylationof thioamides by detailed investigation of reaction parameters including palladiumsource, solvent, reaction temperature, ligand, catalyst loading, and base.3. Substrate scope for the α-arylation of thioamides was investigated under theoptimized conditions.