Photochemical Oxidative Cleavage and Dihydroxylation of Unsaturated Fatty Acids Using Triplet Nitroarenes

Abstract

The widespread use of bio-derived lipids as renewable feedstock chemicals requires their synthetic modification for downstream applications. Herein, we demonstrate the use of nitroarenes as photo-responsive oxidants for the synthesis of aldehydes and 1,2-diols from unsaturated fatty acids. This approach addresses the conventional use of hazardous and toxic reagents such as ozone (O₃) and osmium tetroxide (OsO₄). The successful employment of stable and nontoxic nitroarenes in oxidation chemistry is demonstrated on a series of industrially relevant fatty acids including carboxylic acids and their methyl ester equivalents producing oxygen-enriched substrates.