The copper-catalyzed arylation and vinylation of nitrogen nucleophiles is a highly versatile method for the construction of sp2 C–N bonds. Copper-catalyzed C–N bond formation has an extensive history and the field has been reinvigorated with the development of ligand-promoted catalyst systems that provide general and effective reactions under relatively mild conditions. Copper promotes arylation and vinylation of a wide range of nitrogen nucleophiles, including amines, nitrogen heterocycles, and amide derivatives. The reactivity profile is complementary to that of palladium and often offers orthogonal chemoselectivity. This chapter presents a thorough overview of the copper-catalyzed coupling of aryl and vinyl halides with nitrogen nucleophiles. Current understanding of the mechanism of this process is presented along with a detailed overview of the scope and limitations of this reaction along with optimal reaction conditions for the coupling of various nitrogen nucleophile classes.