Prior to the discovery of this catalytic olefin-imine metathesis (C=C bond cleavage) reaction, as part of our continued commitment to the development of unconventional bond transformation schemes, we have previously identified a complementary C-C bond (enaminone C carbonyl -C β bond) cleavage reactivity. In particular, an otherwise infeasible C-C bond cleavage has been achieved through "neighboring appendage participation" (Scheme 3 With the optimized reaction condition established, the substrate scope is then examined. To this end, the enaminone reactivity is first inspected by employing 2a as the metathesis partner (Table ). The para substitution at the phenyl ring of 1a proves compatible with the transformation, irrespective of the electronic character of the substituent. The yield stands at 33% for an electron-donating methyl group (1b). A similar yield of 32% is observed when changed to a phenyl group (1c). A more electronically donating methoxy group (1d) promotes the yield to 45%. An electron-withdrawing fluorine substituent (1e) gives a 32% yield. An iodine substituent (1f) drops the yield to 27%. Significantly, the resulting olefin-imine Table . Substrate scope of enaminones.