Fe(TAML)Li/(diacetoxyiodo)benzene-Mediated Oxidation of Alcohols: Evidence for Mild and Selective C-O and C-C Oxidative Cleavage in Lignin Model Transformations

A novel combination of Fe(TAML)Li and (diacetoxyiodo)benzene for the oxidation of primary and secondary alcohols at 25 °C in acetone is reported. In view of the interesting ability of this system to selectively cleave specific types of C–C bonds of elaborated alcohols, the application of this novel combination to the oxidative cleavage of lignin model molecules was investigated. Considering the numerous supported versions of the oxidant as well as the mild conditions employed, the developed methodology appears to be a promising lignin depolymerization strategy. Various alcohols have been oxidized by using an unprecedented combination of Fe(TAML)Li and DAIB as the oxidant. The developed conditions showed promising results for the depolymerization of lignin, with model molecules being successfully cleaved under mild conditions.