Pd-Catalyzed Diastereoselective Trifluoromethylthiolation of Functionalized Acrylamides

The Pd-catalyzed diastereos elective trifluoromethylthiolation of acrylamides was developed to allow the formation of the Z-isomer as a single product. Using a C-H bond functionalization strategy, the method was applied to a broad range of a aryl, alpha-alkyl, and alpha,beta-disubstituted acrylamides bearing the amide derived from the 8-aminoquinoline as a directing group. Mechanistic studies as well as postfunctionalization of the products were performed. This approach opens new routes to unprecedented SCF3-containing scaffolds.