Cobalt has become increasingly prominent in organic synthesis, especially in facilitating complex and selective transformations. Among the various cobalt complexes employed, cobalamin, a porphyrinoid with a cobalt(III) centre, stands out as a biologically derived catalyst harnessed for various synthetic applications. The cobalt-catalysed transformations, like C-C coupling, hydrogenation, oxidation, dehalogenation, etc., benefit from the unique coordination environment provided by the macrocycle, which can be finetuned to enhance selectivity and reactivity. However, the field of metalloporphyrinoid chemistry is significantly richer, with modified porphyrin scaffolds such as carbaporphyrins emerging as particularly versatile platforms for a range of organometallic transformations. These macrocycles, featuring carbon atoms in place of one or more of the nitrogen atoms typically found in the porphyrin core, have demonstrated unique reactivity profiles compared to their conventional porphyrin counterparts, especially in transition metal coordination chemistry. The carbaporphyrin cavity exhibits a high degree of electronic tunability, stabilising a broader range of metal ions and unusual oxidation states. This feature makes carbaporphyrins particularly appealing for facilitating novel chemical transformations, especially in cobaltinduced reactions. Cobalt complex of N-confused porphyrin (NCP), the first among carbaporphyrins, quite effectively catalyses cyclopropanation reaction. On the other hand, the forced proximity of the (typically) aryl fragment to the metal centre within the macrocycle creates unique conditions that could facilitate its selective functionalisation. Thus, NCP reacted with a cobalt source can get functionalised at the inner C (21) atom with an oxygen atom, cyano, 2-chlorovinyl, methyl, or tolyl groups, depending on the reaction conditions. Here, the C(sp )-H activation and functionalisation of an α-carbon atom in ketones within metallocarbaporphyrins remain underexplored.