Transition-metal-catalyzed transformations of C–N single bonds: Advances in the last five years, challenges and prospects

Base-promoted direct E-selective olefination of organoammonium salts with sulfones toward stilbenes and conjugated 1,3-dienes

“…Therefore, the development of methodologies for organoammonium salts’ transformation has, to a certain extent, promoted the conversion and use of amines. 1 Since the pioneering Ni-catalyzed Kumada type coupling of organoammonium salts reported by Wenkert and co-workers in 1988, 2 the use of organoammonium salts as electrophiles in organic synthesis has attracted considerable attention. Over the past few decades, a great deal of chemical manipulations of organoammonium salts have been developed by MacMillan, 3 Wang, 4 Watson, 5 Uchiyama, 6 Yu, 7 Zhao 8 and others 9 to build various kinds of C–C bonds and C–heteroatom bonds via C–N bond cleavage, which fully demonstrated the diverse reactivity and the synthetic value of organoammonium salts.…”

Transamidation and Decarbonylation of N-Phthaloyl-Amino Acid Amides Enabled by Palladium-Catalyzed Selective C–N Bond Cleavage

“…Transamidation, as an important amide C–N bond activation reaction, has an irreplaceable role in the synthesis of multifunctional amides, and especially in the diversification of the inherent amide bonds of many biologically active molecules. However, the C–N linkage of amide, especially secondary amide, tends to be chemically inert due to the resonance effect .…”

Cobalt(II)-Catalyzed C–H and N–H Functionalization of 1-Arylpyrazolidinones with Dioxazolones as Bifunctional Synthons

“…The C–N bond is one of the most important chemical bonds in pharmaceuticals, natural products, and functional materials . Thus, significant efforts have been devoted for developing practical and effective synthetic methods to form C–N bonds in organic molecules.…”