Metal-Free Chemoselective Oxidative Dehomologation or Direct Oxidation of Alcohols: Implication for Biomass Conversion

A transition metal-free, chemoselective reaction was performed using the sodium tert-butoxide-oxygen ((NaOBu)-Bu-t-O-2) system, resulting in either oxidative dehomologation or direct oxidation of alcohols. In particular, the newly developed protocol may be used to predict the major product formed, which depends on alkyl chain length of the alcohols and reaction conditions. The rational mechanism of this transformation was also demonstrated by performing an O-18 isotopic labelling experiment. This protocol presents a straightforward method for biomass conversion of a lignin model compound to phenol and benzoic acid.