Catalytic Radical-Triggered Annulation/Iododifluoromethylation of Enynones for the Stereospecific Synthesis of 1‑Indenones

A new Pd­(II)-catalyzed annulation/iododifluoromethylation of enynones has been developed for the synthesis of versatile 1-indanones with moderate to good yields (26 examples). The present strategy enabled the concomitant incorporation of two important difluoroalkyl and iodo functionalities into 1-indenone skeletons with (E)-stereoselectivity. The mechanistic pathway was proposed, consisting of the difluoroalkyl radical-triggered α,β-conjugated addition/5-exo-dig cyclization/metal radical cross-coupling/reductive elimination cascade.