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A Re-catalyzed C-H/C-C bond activation with cyclopropene process described in this work.The results show tuning of bases can introduce interesting product diversity.By employing three different bases namely,PhMgBr,LitBuO and NaHwe successfully carried of C-H alkenylation,hydroarylation and C-H allylation with cycloprpene moiety.We were also able to isolate and fully characterize,for the first time,elusive irnidorhenacycle intermediate which also manifests comparable catalytic activity.Comparison of NMR and Mass spectroscopic studies of the different C-H activation pathways illuminate the probable reaction pathways for this protocol.We also demonstrated an important transformation of C-H alkenyl product by simply manipulating with N-Iodosuccinimide.