In summary, a catalytic olefin-imine metathesis process has been discovered herein, revealing unique synthetic requirements for achieving this hitherto elusive reaction mode. A cobalt catalysis protocol for amidine olefination with enaminones has been developed, allowing convenient access to primary aminebearing enaminones. Experimental evidence is consistent with a mechanistic sequence of amine-imine group exchange, cobalt-catalyzed cyclization, and ring fragmentation. The primary amine-featured enaminones can serve as a versatile synthon for diversification into a broad range of structures, highlighting the enormous potential utility of our enabling synthetic methodology.