Palladium-Catalyzed Activation And Transformation Of Benzylammonium Salts C-N Bond

In recent years, transition-metal-catalyzed cleavage of C-N single bonds has become a hot area, because it provides either an excellent nitrogen source or an excellent carbon source from readily available and simple N-containing compounds to construct useful molecules. It also provided a method for synthesizing useful molecules from simple and easy available N-containing compounds. Generally, it is difficult to break the C-N bonds. So it has become an important approach of breaking C-N bond which is through activating the inactive N-containing compounds into diazo compound or ammonium salts.Ammonium salts action as a convenient and readily available N-containing, which has attracted much attention. Recently, there are more and more reports about nickel-catalyzed C-N bonds activation of ammonium salts; However, palladium-catalyzed reactions of ammonium salts are scarce.This paper focused on the studies of palladium-catalyzed reactions of benzyl ammonium salts via C-N bonds broken. The main contents are shown as follow:?1? Palladium-catalyzed Suzuki crossing coupling between benzyl ammonium salts via C-N bonds activation and organic boron reagents. In this reaction, we obtained excellent yields of desired products while we selected the catalytic system of PdCl₂/PPh₃, in the solvent of ethanol at 100?. There are some advantages such as simple operation, wide range of substrates, good tolerance of functional group in the reaction.?2? We developed a new method of constructing amide. We had synthesize a wide range of derivate of phenylacetamide through palladium-catalyzed carbonylation between benzyl ammonium salts and amine, which undergo C-N bonds cleavage of ammonium salts.