Bioinspired oxidative cleavage of aliphatic C–C bonds of the acireductone model substrate 2‐hydroxy‐3‐oxo‐1,3‐diphenylprop‐1‐en‐1‐olate, bound to two paramagnetic nickel(II) complexes that are mimics for the nickel containing acireductone dioxygenase, has been achieved utilizing aerial oxygen under ambient conditions.