Palladium-Catalyzed Regioselective Coupling Of Amidines And 1,2,3-Triiodobenzenes: Facile Synthesis Of 2,3-Diiodinated N-Arylbenzimidamides As Potential Mdm2 And Mdm4 Inhibitors

A facile and unprecedented synthesis of 2,3-diiodinated N-arylbenzimidamide derivatives through highly regioselective Buchwald-Hartwig coupling of 5-substituted-1,2,3-triiodobenzene and amidine is described. Remarkably, the amination reactions are proceeded exclusively at the terminal positions, the less sterically hindered, and the most regioactive positions. The highest yields were isolated from a combination between electron-poor 1,2,3-triiodoarenes and electron-poor benzimidamides. The optimized conditions were found to be suitable for many functional groups. This report discloses the first method to make 2,3-diiodinated N-arylbenzimidamides that is efficient, general in scope, highly regioselective, and truly remarkable precursors for other transformations