Indium-Mediated Synthesis of Benzylic Hydroperoxides.

An indium(0)-metal-mediated efficient synthesis of benzylic hydroperoxides is described. The reaction proceeds efficiently with a broad range of benzyl bromides under aerobic conditions at room temperature to afford benzyl hydroperoxides in good to excellent yields. In addition, the tandem hydroperoxidation-Michael addition of ( E)-1-(bromomethyl)-2-(2-nitrovinyl)benzene was also demonstrated.