Some oxidative additions proceed analogously to the well known bimolecular nucleophilic substitution reactions in organic chemistry. Nucleophilic attack by the metal center at the less electronegative atom in the substrate leads to cleavage of the R–X bond, to form an [M–R] species. This step is followed by rapid coordination of the anion to the cationic metal center. For example, reaction of a square planar complex with methyl iodide:
This mechanism is often assumed in the addition of polar and electrophilic substrates, such as alkyl halides and halogens.