Selective Oxidations of Alcohols by Bromine in Combination with Nickel(II) Benzoate

Abstract

The combination of nickel(II) bromide with benzoyl peroxide serves as an effective reagent for the conversion of secondary alcohols to ketones and, when nickel(II) bromide is employed as an alcohol template, for the oxidation of primary alcohols to aldehydes.¹ The unique steric selectivity of the Bz₂O₂/NiBr₂ combination has recently been demonstrated in oxidations of 2,2-disubstituted-1, 4-butanediols to the corresponding β,β-disubstituted-γ-butyrolactones.² In the course of our investigation of this novel oxidative method, we have discovered that molecular bromine in combination with commercially available nickel(II) benzoate is a mild, effective, and selective oxidant for the conver-