Synthesis of Oxazoline-spirocyclohexadienone via Electrochemical Dearomatization of Phenol Derivatives

Abstract

Oxazoline and spirocyclohexadienone moieties are prevalent in natural products and biologically active molecules. Herein, we report an efficient method for the synthesis of oxazoline-spirocyclohexadienones via electrochemistry-mediated oxidative dearomatization of phenol derivatives, utilizing amide side chains as nucleophiles. This approach features the employment of anodic oxidation strategy, circumventing the need for traditional oxidizing agents. A diverse range of oxazoline-spirocyclohexadienones are obtained in moderate to excellent yields (15–97 %). Cyclic voltammetry experiments reveal that the solvent plays a crucial role in this transformation and this reaction involves two consecutive single-electron transfer events.