An iridium(III)-mediated C–H functionalization sequence involving a concerted cyclometalation–deprotonation/migratory insertion pathway is reported for the undergraduate chemistry laboratory. The air- and water-stable iridacycle intermediates are readily isolated and characterized by NMR spectroscopy. Both steps of the experiment are performed at room temperature under benchtop conditions, rendering the protocol suitable for a wide range of student skill levels.
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