Syntheses of Diarylmethanes Via an Oxidative Benzylic Functionalization of P-Alkyl Phenol Derivatives Under Quaternary Ammonium Hypoiodite Catalysis.

ABSTRACT

We herein report two strategies for the quaternary ammonium hypoiodite-mediated oxidative benzylic functionalization of p-alkyl phenol derivatives. By using either dibenzoylperoxide or H2O2 in hexafluoroisopropanol in the presence of tetrabutyl ammonium iodide gives access to activated intermediates which can then be coupled with electron-rich aromatic compounds. Overall, this sequential two-step one-pot procedure gives access to diversely decorated diarylmethane derivatives straightforwardly. Furthermore, the suitability of these products to undergo further oxidation reactions was successfully demonstrated.