KMnO4-catalyzed chemoselective deprotection of acetate and controllable deacetylation–oxidation in one pot

Abstract

A novel and efficient protocol for chemoselective deacetylation under ambient conditions was developed using catalytic KMnO₄. The stoichiometric use of KMnO₄ highlighted the dual role of a heterogeneous oxidant enabling direct access to aromatic aldehydes in one-pot sequential deacetylation–oxidation. The reaction employed an alternative solvent system and allowed the clean transformation of benzyl acetate to sensitive aldehyde in a single step while preventing over-oxidation to acids. Use of inexpensive and readily accessible KMnO₄ as an environmentally benign reagent and the ease of the reaction operation were particularly attractive, and enabled the controlled oxidation and facile cleavage of acetate in a preceding step.