A convenient catalytic oxidative 1,2-shift of arylalkenes for preparation of a-aryl ketones mediated by NaI

Using a catalytic amount of NaI and a stoichiometric oxidant Oxone(@), a convenient procedure has been developed for the catalytic oxidative 1,2-shift of arylalkenes in CH3CN/H2O at room temperature, which provides the corresponding a-aryl ketones in moderate to good yields. In this protocol, sodium iodide is first oxidized into hypoiodous acid, which reacts with arylalkene to afford iodohydrin. Then, the iodohydrin is transformed into the a-aryl ketone via an oxidative 1,2-shift rearrangement. (C) 2014 MM Zhu. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.