Nucleophilic attack of intramolecular hydroxyl groups on electron-rich aromatics using hypervalent iodine(III) oxidation

The hypervalent iodine(III) reagent, phenyliodine bis(trifluoroacetate) (PIFA)-mediated oxidative nucleophilic substitution of electron-rich aromatics involving aromatic cation radical intermediates was utilized in the direct aromatic carbon-oxygen bond formation reaction, and a novel and simple synthetic method for chroman derivatives was developed. As an extension of this methodology, a facile access to spirodienone derivatives was also achieved.