This review focuses on the progress of the use of the hypervalent iodine reagent PIFA in the intramolecular olefin amidation reaction as an environmentally benign alternative over other related metal-assisted processes. The key step of this route embraces the oxidation of the nitrogen atom by the I(III) reagent to form an electronically deficient intermediate, and its succeeding trapping by the olefin fragment. A common behavior for a number of tailored designed substrates under such conditions is observed leading to the formation of a broad array of functionalized nitrogen-containing heterocycles.