With the olefin-imine metathesis reaction mechanism elucidated, we next seek to fathom the synthetic utility of the primary amine-bearing enaminone product (Scheme 7). In principle, 3aa can typically react as a nucleophile at both the amine and C β sites. This is evidenced by the copper-catalyzed N-arylation with phenyl boronic acid (product 9, 80%) and NBS-mediated C β -thiocyanation with KSCN (product 10, 70%). The C β -thiocyanated 10 can further cyclize into a heterocyclic product 11 (40%) by concurrent exploitation of the nucleophilicity of the amine group. The combined use of amine and C β sites is also demonstrated by the copper-catalyzed [3+3] annulation reaction with propiophenone (product 12, 65%) as well as the radical-based azirination reaction with HOAc (product 13, 50%).