Radical-Induced Cascade Annulation/Hydrocarbonylation for Construction of 2-Aryl-4IH/I-chromen-4-ones

A robust metal- and solvent-free cascade radical-induced C-N cleavage/intramolecular 6-endo-dig annulation/hydrocarbonylation for the synthesis of the valuable 2-aryl-4H-chromen-4-ones is described. This practical synthesis strategy utilizes propargylamines and air as the oxygen source and green carbonylation reagent, in which propargylamines are activated by the inexpensive and available dimethyl 2,2′-azobis(2-methylpropionate) (AIBME) and (PhSe)[sub.2] as the radical initiators. This simple and green protocol features wide substrate adaptability, good functional group tolerance, and amenability to scaling up and derivatizations.