Iridium(III) and rhodium(III) complexes can catalyze the carbocyclization between 2‐phenylimidazo1,2‐a]pyridine and α‐diazo esters. The reaction occurs via C H activation and dialkylation of the arene followed by intramolecular nucleophilic substitution. Iridium(III) and rhodium(III) catalysis offer complementary scopes with respect to the α‐diazo esters.