Iridium(III) and rhodium(III) complexes can catalyze the carbocyclization between 2-phenylimidazo[1,2-a]pyridine and -diazo esters. The reaction occurs via CH activation and dialkylation of the arene followed by intramolecular nucleophilic substitution. Iridium(III) and rhodium(III) catalysis offer complementary scopes with respect to the -diazo esters.